Free Agent Starting Pitchers and Boston

lexrageorge

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There was a recent mini-diversion in the Chris Sale thread regarding the attractiveness of Boston as a destination for starting pitchers. I believe @chawson made the original assertion that the Red Sox have trouble signing free agent pitchers, which raised some discussion. Not wanting to divert the Sale thread any further, I decided to start another thread. I'll leave it to the mods to decide if it's worth moving those posts over from the Sale thread over to this one. Anyway,...

I’d thought I would take some time to at least see if the Sox as an organization have signed more or fewer free agent starting pitchers than other organizations. So, I went back to the 2004-05 offseason and charted the free agent signings of starting pitchers with a cumulative bWAR of 9 or greater over the past 3 seasons.

This analysis is by no means exhaustive. I did not attempt to find old press releases, stories, interviews by free agent pitchers. I did not take into account players that the Sox were interested in or were rumored to be interested in. In the interest of time, I ignored extensions that were signed prior to a player becoming a free agent. I did track re-signings and note those out separately. I ignored opt-outs, opt-ins, players demanding trades, etc. And I did not differentiate one year contracts from multi-year ones. The 9 bWAR cutoff is somewhat arbitrary; it simply means that the player averaged 3 bWAR of the past three seasons. David Price would have qualified based on his past 3 seasons, that seemed to be therefore a reasonable measure of a 1/1A/2 class starter.

Also, there are a lot of ways of building a pitching staff. The Sox have in several notable cases traded for a star pitcher who was nearing free agency (Pedro, Schilling, Beckett, and, of course, Sale). A pitching staff needs a solid mid-to-back end rotation as well, which I’ve ignored. I also ignored relievers, openers, and such.

But, bearing the above in mind, it seemed as if this analysis would at least determine if there is indeed something there about Boston being unattractive to free agent starting pitchers. Note that Boston has had hardly any problem signing free agent position players. And the team has won 4 World Series Titles over the duration of this analysis, and most posters here (although certainly not all) would take that over the Payroll Efficiency Titles that Oakland and Tampa annually compete for.

I'll start with my year-by-year breakdown. The next post will have the summary data and my own conclusions:

2004-05: Pedro was the big prize, despite his 0.259 OPS. He went to the Mets after they offered 4th guaranteed year. The other qualifying pitchers were Clemens (resigned w/ Houston), David Wells, Al Leiter (39 y/o), Matt Clement, Derek Lowe (who was not offered a contract by Boston), and Woody Williams.

2005-06: Slim pickings. Esteban Loaiza and 41 y/o Kenny Rogers were the only qualifiers. The Sox traded for Beckett instead.

2006-07: Jason Schmidt and Barry Zito were the big names. Glavine and Mussina resigned, and then you had Maddux going to the Padres while nearing the end of his career, and Pettite returned to the Yankees after a brief interlude with Roger and the Astros. The Sox did sign Dice-K, but that was because the won a posting fee auction, so Dice-K had no real choice to sign anywhere else, so I will ignore this one. And the Sox signed Julio Lugo, who had also put up a combined 9 bWAR over the past 3 seasons (<insert face palm here>)

2007-08: Pettite and Schilling resigned and Glavine returned to the Braves.

2008-09: CC made the biggest splash, going to the Yankees, along with Felger & Mazz’s favorite free agent of all time, Mark Teixeira. Lowe went to the Braves, while the Sox signed John Smoltz (ugh!). They also signed Brad Penny (double-ugh), who just missed the cut with 8.7 bWAR3. It was unclear if the Sox were ever interested in signing Sabathia, or would have even been in the running had they been.

2009-2010: The biggest prize was John Lackey. Other qualifiers were Pettite (yet again resigned by the Yankees) and Erik Bedard (resigned w/ Seattle).

2010-11: Cliff Lee was the big prize, being scooped by Philly. The Sox instead signed Carl Crawford and traded for Adrian Gonzalez. The only other qualifier was one of the heroes of the 2004 ALCS, Javier Vazquez, who went to the Marlins.

2011-12: Only two pitchers qualified: 2005 playoff hero Mark Buehrle went to the Marlins, and journeyman Edwin Jackson signed with the Nationals.

2012-13: Another year with only two qualifiers, and both resigned (Kuroda with the Yankees, and Anibel Sanchez with the Tigers). Anyone complaining about the Sox approach to free agency that offseason needs to be barred from being a fan of the team. Zach Greinke just missed the cut.

2013-14: This offseason was headlined by Cano and Ellsbury. And yet another year with only two qualifying pitchers: Kuroda, who resigned with the Yankees, and forever young Bartolo Colon who took his talents to Queens.

2014-15: Max Scherzer topped the list, going to Washington. The other qualifier was James Shields (egads). Jon Lester made headlines by spurning Boston’s offer to go to the Cubs, but he did not qualify having a 7.7 bWAR over the prior 3 seasons thanks to his disastrous 2012. I’ve arbitrarily decided to make him an honorable mention. The Sox went all in on Sandoval and Hanley instead.

2015-16: This was a big year for free agent pitchers. The Sox were rumored to be in on Zack Greinke (Arizona) and David Price. Iwakuma resigned with Seattle. Other qualifies included Johnny Cueto (whom the Sox were rumored to be interested in trading for at one point), Jordan Zimmerman (can’t blame Dombrowski for that one; he was with Boston by then), and John Lackey, with Doug Fister just missing the cut.

2016-17: Nada.

2017-18: Jake Arrieta (Phillies) was the only qualifier. Honorable mentions to CC Sabathia and Yu Darvish, who garned a lot of press given the dearth of free agent pitchers during this period.

2018-19: You know pickings are relatively slim when the 5th most prominent pitcher by bWAR3 was Drew Pomeranz. The Yankees went all in, signing Gio Gonzalez, resigning J. A. Happ, and resigning CC yet again as an honorable mention. The Sox resigned Eovaldi, but he did not qualify.
 

lexrageorge

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Summary of results (with re-signings in parantheses):

Sox: 6 (1): Clement, Wells, Lackey, Price, Smoltz(*), Schilling (resigned)

*: Smoltz was coming off a serious injury and signed a one year offer for something like $5M.

A’s: 1
Astros: 1 (1)
Braves: 2
Cubs: 2* (includes Jon Lester)
Diamondbacks: 1
Giants: 2
LA Dodgers: 3* (includes Greinke)
Mariners: 1 (1)
Marlins: 3
Mets: 3 (1)
Nationals: 2
Padres: 3
Phillies: 2
Tigers: 3 (1)
Yankees: 8 (6)

Conclusions: There were only 43 qualifying pitchers over this 14 year period, of which only 32 actually changed teams. Which makes it somewhat difficult to draw a lot of meaningful assertions. I will start by saying it is indeed correct that the Sox "only" signed a handful of top tier free agent starters over this period. Just should be noted that only the Yankees have signed more.

There were clearly years where the Sox were not pursuing free agent starters for various reasons. And some years the pickings were mighty slim. And some of the headline contracts have turned disastrous, so it's not exactly upsetting that the Sox missed on some of those. There are still 14 teams that have not signed a high-profile free agent starting pitcher.

If Boston is unattractive to prospective free agent pitchers, the data do not yet reflect that sentiment.
 

Mueller's Twin Grannies

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I don't see how Boston couldn't be appealing to free agent pitchers given they are always competitive (or endeavor to be), have deep pockets, a passionate fanbase (which does matter to some guys), and a storied history. That's usually stuff baseball players eat up.

If there's anything that can be pegged as the reason the Red Sox aren't always in the thick of free agent pitcher pursuits, it's likely timing. They either don't need the pitcher (at the price said pitcher will likely command) or they don't want to spend so much money on one guy and would rather spread the wealth and have more depth/greater value. When the really good names come up for free agency, it has generally, seemingly, coincided with periods where Boston wasn't looking to spend big on arms or free agents.
 

Savin Hillbilly

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The wrong side of the bridge....
Part of the equation is how much, if anything, do the Red Sox have to outbid their opponents by in order to land a FA pitcher.
But since we have no way of knowing the answer to this, it becomes just a vehicle for reinforcing assumptions. I.e., if you think pitchers hate the idea of pitching in Boston, you can assume that they would have signed for X percent less somewhere else, and there's no way of refuting or confirming that.
 

chrisfont9

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Having taken part in the original discussion, I analogized the Sox' position to that of the Celtics: not an automatic destination for geographic (and maybe cultural) reasons, given the number of southerners and Californians in the game, but with some unique qualities and a case to be made around winning. So I don't know that anyone called Boston "unattractive" but like the Celtics, there are a couple other cities they have a hard time competing with. A ton of these guys already live in Florida or Texas and need to be talked out of signing close to home. Just as NBA players tend to live increasingly in LA, and are always looking at Miami too.

Clearly the Sox have some ability to target guys who *are* open to playing in Boston, and then they can compete for talent. And since we are limiting this to starting pitching, the Sox are a regular and enthusiastic buyer too, since we haven't developed anyone since the Bush administration. So just talking out my ass here but my hunch is that free agents are either open to Boston and then it's a simple bidding war with a level playing field, or they aren't open and the subject is closed.
 

YTF

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With Porcello, Holt, Moreland, Pearce, Nunez and Thorburg coming of the books that frees up about $44.5 M. Roughly $23 M of that will be eaten up by the Sale and Bogaert extensions leaving about $21.5 M. How much of that goes toward first base (do you try JD there? Maybe Chavis with Marco at second?) Your going to have to either resign Holt or find his equivalent somewhere. So between those two holes what's left of the $21.5 M? There is also the matter of any players who may be arbitration eligible, so what's left after that? We know the Sox will need one starter with Porcello leaving (fingers are crossed for both Sale and Eovaldi) and the closer situation is going to need to be resolved. So pending some creativity or making a trade there will once again be very little wiggle room between anything that the Sox potentially gain from departing players and the salary threshold that they look to maintain. That said I haven't considered the fact that JD could opt out at the end of this season as I see no reason that he would and I haven't factored in the additional $1.58 M that the Sox shed from the remainder of Cashner's contract because he could be back at $10 M next season. It's complicated with a vesting option or player option pending his combined innings pitched in the '18 and '19 seasons. Also, there is also the distinct possibility that there other other considerations that I've missed.
 

chrisfont9

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Related, why are the Sox always seemingly on everyone's "no trade" list? Because they don't want to go there, or because they view Boston as a likely trader so when the subject of being traded there comes up, the player wants to wield the NTC as a weapon to get something back?
 

shaggydog2000

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I don't see how Boston couldn't be appealing to free agent pitchers given they are always competitive (or endeavor to be), have deep pockets, a passionate fanbase (which does matter to some guys), and a storied history. That's usually stuff baseball players eat up.

If there's anything that can be pegged as the reason the Red Sox aren't always in the thick of free agent pitcher pursuits, it's likely timing. They either don't need the pitcher (at the price said pitcher will likely command) or they don't want to spend so much money on one guy and would rather spread the wealth and have more depth/greater value. When the really good names come up for free agency, it has generally, seemingly, coincided with periods where Boston wasn't looking to spend big on arms or free agents.
Or they would rather trade for a cost controlled younger starter who likely has a higher chance of repeating past performance than most free agents who are older and exiting their primes would.
 

Red(s)HawksFan

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Part of the equation is how much, if anything, do the Red Sox have to outbid their opponents by in order to land a FA pitcher.
The only pitcher during the examined period for whom they really went full out bidding war to land was Price. Lackey reportedly came to them looking for an offer, so I'm not sure he fits as someone they had to outbid anyone for even though he got a high priced deal. Everyone else they either weren't all that in on in the first place (like CC or Scherzer), or they were in on them but were out-bid which I think says more about their desire to stick to valuations than the player's feelings on the city/franchise.
 

chrisfont9

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With Porcello, Holt, Moreland, Pearce, Nunez and Thorburg coming of the books that frees up about $44.5 M. Roughly $23 M of that will be eaten up by the Sale and Bogaert extensions leaving about $21.5 M. How much of that goes toward first base (do you try JD there? Maybe Chavis with Marco at second?) Your going to have to either resign Holt or find his equivalent somewhere. So between those two holes what's left of the $21.5 M? There is also the matter of any players who may be arbitration eligible, so what's left after that? We know the Sox will need one starter with Porcello leaving (fingers are crossed for both Sale and Eovaldi) and the closer situation is going to need to be resolved. So pending some creativity or making a trade there will once again be very little wiggle room between anything that the Sox potentially gain from departing players and the salary threshold that they look to maintain. That said I haven't considered the fact that JD could opt out at the end of this season as I see no reason that he would and I haven't factored in the additional $1.58 M that the Sox shed from the remainder of Cashner's contract because he could be back at $10 M next season. It's complicated with a vesting option or player option pending his combined innings pitched in the '18 and '19 seasons. Also, there is also the distinct possibility that there other other considerations that I've missed.
Also Sandoval goes from $19m to a final $5m buyout, so another -$14m for them to maybe spend.
 

Red(s)HawksFan

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Related, why are the Sox always seemingly on everyone's "no trade" list? Because they don't want to go there, or because they view Boston as a likely trader so when the subject of being traded there comes up, the player wants to wield the NTC as a weapon to get something back?
Considering that players that name the Red Sox often also name teams like the Yankees and Dodgers, I think it has more to do with negotiating power. Frankly no matter who the player or what teams are listed, NTCs are all about leverage, and probably only rarely have to do with a player simply not wanting to play for certain teams or in certain markets.
 
Jul 5, 2018
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But since we have no way of knowing the answer to this, it becomes just a vehicle for reinforcing assumptions. I.e., if you think pitchers hate the idea of pitching in Boston, you can assume that they would have signed for X percent less somewhere else, and there's no way of refuting or confirming that.
I doubt if there are example of someone choosing a comparable offer from some other team over the Sox. I believe that players are generally going to take the best offer. Pedro presumably enjoyed playing for Boston, but even though he had already made $80M+ in his career, he went for the extra year with the Mets.
 

Lose Remerswaal

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With Porcello, Holt, Moreland, Pearce, Nunez and Thorburg coming of the books that frees up about $44.5 M. Roughly $23 M of that will be eaten up by the Sale and Bogaert extensions leaving about $21.5 M. How much of that goes toward first base (do you try JD there? Maybe Chavis with Marco at second?) Your going to have to either resign Holt or find his equivalent somewhere.
I expect Holt to be back and 1B to be filled by some combo of him, Chavis, and a cheap veteran who goes unsigned somewhere. 2B to be filled by Holt/Chavis/Marco/Lin
 

Mueller's Twin Grannies

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I doubt if there are example of someone choosing a comparable offer from some other team over the Sox. I believe that players are generally going to take the best offer. Pedro presumably enjoyed playing for Boston, but even though he had already made $80M+ in his career, he went for the extra year with the Mets.
I recall that the buzzword surrounding those negotiations was "respect." To Pedro, years meant more than money in terms of respect. Anyone can pay you an exorbitant amount but to want to keep you around long-term was what he was looking for and he felt he'd earned the benefit of the doubt for that guaranteed fourth year. Theo, et al, disagreed and so he left. At least there was no acrimony and he's back in the fold now. But I think he was mostly looking for security for the next few years and three just wasn't the magic number.
 

YTF

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I expect Holt to be back and 1B to be filled by some combo of him, Chavis, and a cheap veteran who goes unsigned somewhere. 2B to be filled by Holt/Chavis/Marco/Lin
I do as well, but you never know. My guess is that he would prefer to stay in Boston. He seems to enjoy it here and has invested himself in the community, but this may be his shot at his biggest pay day. There seems to be more demand than ever for multi-positional talent. I think there might be more guys in the game now that have really embraced this and have realized it to be the one true for them to get at bats. My God I know what they're doing is next level, but look at the construction of The Dodger's lineup. It seems like 2/3 of the roster plays at least two positions and there seems to be plenty of ABs to go around. With that in mind, like you I see Chavis assuming that role to some degree as well as the three man approach at second. It keeps guys active without wearing them down, though it looks like Chavis or Marco could handle it for a prolonged period of time. Again I agree with your take on first base which is what we've seen for a portion of this season, but I'm wondering if Sam Travis may have finally arrived. Hopefully he gets semi-regular ABs to finish out this season and does well playing fall or winter ball somewhere during the off season and keeps it rolling into spring training.
 
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I recall that the buzzword surrounding those negotiations was "respect." To Pedro, years meant more than money in terms of respect. Anyone can pay you an exorbitant amount but to want to keep you around long-term was what he was looking for and he felt he'd earned the benefit of the doubt for that guaranteed fourth year. Theo, et al, disagreed and so he left. At least there was no acrimony and he's back in the fold now. But I think he was mostly looking for security for the next few years and three just wasn't the magic number.
The Red Sox were concerned about Pedro's durability and rightfully so. Their offer was a good one and the Sox shouldn't have been expected to match the Mets' above market offer and it turned out to be a bad contract for the Mets.

I looked it up and Pedro made $90 million with the Sox so security shouldn't have been an issue. I'm not criticizing Pedro; I'm just using his case as being an example of players going for top dollar.
 

Yelling At Clouds

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I doubt if there are example of someone choosing a comparable offer from some other team over the Sox. I believe that players are generally going to take the best offer. Pedro presumably enjoyed playing for Boston, but even though he had already made $80M+ in his career, he went for the extra year with the Mets.
Maybe now that teams' offers to free agents are reportedly becoming more similar because of collusion more teams relying on proprietary player valuation systems, we can start finding out who really values what!

More seriously, I think the actual answer is "there are a lot of factors that a player considers when picking a new team, with money usually - but not always - the biggest one, but things rarely work out in such a way that it ever makes that big of a difference." In other words, it's possible that there have been pitchers who have been reluctant to come to Boston for that reason (as Schilling, not a free agent, famously was), but it probably only comes into play in the really specific instance of the Red Sox having a near-identical offer to some other team.
 

Lose Remerswaal

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Again I agree with your take on first base which is what we've seen for a portion of this season, but I'm wondering if Sam Travis may have finally arrived. Hopefully he gets semi-regular ABs to finish out this season and does well playing fall or winter ball somewhere during the off season and keeps it rolling into spring training.
I forgot about Travis, thank you for bringing him up. I had written him off before this season, but he has showed he belongs in the mix for 2020
 

Cesar Crespo

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I forgot about Travis, thank you for bringing him up. I had written him off before this season, but he has showed he belongs in the mix for 2020
He actually fits in really well if they want to go Chavis/Travis at 1b and Marco/Chavis at 2b. I don't know if they want to hand Marco the large half of a platoon though.
 

lexrageorge

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Related, why are the Sox always seemingly on everyone's "no trade" list? Because they don't want to go there, or because they view Boston as a likely trader so when the subject of being traded there comes up, the player wants to wield the NTC as a weapon to get something back?
I do not believe the Red Sox are on that many no-trade lists, and I highly doubt they are on an inordinate number of such lists. Again, such an assertion needs evidence that goes beyond citing media reports that say "OMG, star player X has Boston on its no trade list!!". The reality is that the Sox have had little trouble trading for big name players when they wanted to. And, as noted, such clauses are often used for leverage.
 

Plympton91

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He actually fits in really well if they want to go Chavis/Travis at 1b and Marco/Chavis at 2b. I don't know if they want to hand Marco the large half of a platoon though.
Why Marco instead of Holt? I don’t think Holt will be prohibitively costly and is vastly underrated given his utility man status, plus his age and the multiple concussion issues will also make teams unwilling to go long term crazy.

The pen is working itself out. They just need a fifth starter, who they hopefully can get for Lance Lynn money 3/$10, or less.
 

Plympton91

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Having taken part in the original discussion, I analogized the Sox' position to that of the Celtics: not an automatic destination for geographic (and maybe cultural) reasons, given the number of southerners and Californians in the game, but with some unique qualities and a case to be made around winning. So I don't know that anyone called Boston "unattractive" but like the Celtics, there are a couple other cities they have a hard time competing with. A ton of these guys already live in Florida or Texas and need to be talked out of signing close to home. Just as NBA players tend to live increasingly in LA, and are always looking at Miami too.
I think that has a lot to do with weather and so isn’t as much of a hindrance for the Red Sox. Being in Boston from April through October is quite pleasant; being in Boston from October through April absolutely sucks.
 

Savin Hillbilly

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The wrong side of the bridge....
He actually fits in really well if they want to go Chavis/Travis at 1b and Marco/Chavis at 2b. I don't know if they want to hand Marco the large half of a platoon though.
Why not? He's been essentially as good a hitter as the other two in his short MLB career (Marco 92/Chavis 96/Travis 86) and a better one in 2019, albeit in a tiny sample (109/96/97). And he hasn't so far had all that much trouble against LHP, so they could go Marco 2B/Travis 1B when Chavis needs a day off.

It's far from ideal, but it might be as good as any other solution available. The Sox could try to trade for a 1B or 2B, of course, but it seems like whatever tradeable assets they have would be better spent on pitching. The only FA candidates at either position who seem remotely worth pursuing are Abreu at 1B and Dozier and Schoop at 2B, and I'm not sure any of them would be enough of an improvement to be worth even a modest investment.
 

Cesar Crespo

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Why Marco instead of Holt? I don’t think Holt will be prohibitively costly and is vastly underrated given his utility man status, plus his age and the multiple concussion issues will also make teams unwilling to go long term crazy.
Holt is fine too but he has that utility man status so I assume they'd continue using him in that role.
Why not? He's been essentially as good a hitter as the other two in his short MLB career (Marco 92/Chavis 96/Travis 86) and a better one in 2019, albeit in a tiny sample (109/96/97). And he hasn't so far had all that much trouble against LHP, so they could go Marco 2B/Travis 1B when Chavis needs a day off.
Because Marco is largely unproven and wasn't a top prospect like Chavis was and he's always injured. Plus his minor league track record suggests he's going to struggle vs lefties. Travis would be in a much more limited role.
 

Plympton91

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Holt is fine too but he has that utility man status so I assume they'd continue using him in that role.


Because Marco is largely unproven and wasn't a top prospect like Chavis was and he's always injured. Plus his minor league track record suggests he's going to struggle vs lefties. Travis would be in a much more limited role.
At risk of contributing further to the thread derailment, power hitting first basemen have been severely downgraded in value the past couple offseasons. They can probably bring back Pearce on a minor league deal and Moreland for $5 million if they want to go that route, and leave Chavis for optionable depth
 

TrotNixonsHat

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I remember that before Schilling came here, Boston had a hard time getting free agent pitchers. He was the guy who flipped the script a little bit (even though he came in via trade, he had a NTC and it was similar to courting a FA.)

In the 2000 offseason, the Red Sox main free agent target was actually Mike Mussina. The main hangup was that he wanted a NTC, but also I think the stigma of pitching in Fenway was part of why he chose the MFY offer. It all worked out because Manny was the more valuable player, and he won two rings in Boston (compared to Moose's 0 rings in New York) but I remember that being more evidence that free agent pitchers didn't want to come here.
 

chawson

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Summary of results (with re-signings in parantheses):

Sox: 6 (1): Clement, Wells, Lackey, Price, Smoltz(*), Schilling (resigned)

*: Smoltz was coming off a serious injury and signed a one year offer for something like $5M.

A’s: 1
Astros: 1 (1)
Braves: 2
Cubs: 2* (includes Jon Lester)
Diamondbacks: 1
Giants: 2
LA Dodgers: 3* (includes Greinke)
Mariners: 1 (1)
Marlins: 3
Mets: 3 (1)
Nationals: 2
Padres: 3
Phillies: 2
Tigers: 3 (1)
Yankees: 8 (6)

Conclusions: There were only 43 qualifying pitchers over this 14 year period, of which only 32 actually changed teams. Which makes it somewhat difficult to draw a lot of meaningful assertions. I will start by saying it is indeed correct that the Sox "only" signed a handful of top tier free agent starters over this period. Just should be noted that only the Yankees have signed more.

There were clearly years where the Sox were not pursuing free agent starters for various reasons. And some years the pickings were mighty slim. And some of the headline contracts have turned disastrous, so it's not exactly upsetting that the Sox missed on some of those. There are still 14 teams that have not signed a high-profile free agent starting pitcher.

If Boston is unattractive to prospective free agent pitchers, the data do not yet reflect that sentiment.
I appreciate you taking the time to dive into this — and I agree with you that some big-ticket free agent signings certainly did not work out for other teams — but at first glance this analysis seems incomplete. I'm also confused by your criteria, and why you're using the outcome-based bWAR rather than the contracts themselves.

- Carl Pavano was the prize in the 2004-05 offseason, and Theo was in on him. He's omitted in your year-by-year breakdown. As a fan of the team, I'm glad it didn't work out, but the Sox whiffing on him while letting Pedro and Lowe walk meant they needed to make up 400 innings quick, which led them to go after Clement.

- Why is Smoltz counted here as a major free agent signing? He wasn't a coveted free agent, he was a late-career/scrap heap flyer that didn't work out. Same with Wade Miller, Brad Penny, Bartolo Colon, Doug Fister, Paul Byrd, etc. I think those guys are somewhat outside the scope.

- Why are we counting Schilling — a guy the Sox traded for — re-upping with the team on a couple one-year deals and not counting, say, Eovaldi? I think it definitely *is* common practice for the Sox to trade for a guy and then try to sign or extend him (Schilling, Porcello, Beckett, Eovaldi, Pedro). The Cardinals often do this too (see Paul Goldschmidt), and like to see that a player fits with their climate. This seems necessary for a pressure-cooker city like Boston.

- The Dodgers, to take one team in your list, have signed well more than *three* free agents over that time. Jason Schmidt was a huge one; he just got hurt. Others that fit your criteria off the top of my head include McCarthy, Greinke, Wolf, Capuano, Kazmir, Ryu, Kuroda, Rich Hill, Aaron Harang, Ted Lilly, and Derek Lowe. They also spent big money extending Kershaw, Billingsley, and Brad Penny. You have the Giants signing two guys, but from memory they've signed Cueto, Samardzija, Zito, Hudson, Matt Morris, Vogelsong, et al. over that period.

- Is it really helpful to compare the Sox' ability to sign FA pitchers compared to small market teams like the Marlins, Tigers and Padres? Ironically, I think it was reported that Theo [edit: Cherington] lost out to the Marlins on Buehrle in 2012, but typically those teams have wildly different contention cycles, budgets and business models and are not pulling from the same pool.
 
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lexrageorge

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I appreciate you taking the time to dive into this — and I agree with you that some big-ticket free agent signings certainly did not work out for other teams — but at first glance this analysis seems incomplete. I'm also confused by your criteria, and why you're using the outcome-based bWAR rather than the contracts themselves.
Thanks for your feedback; much appreciated in terms of moving the discussion forward.

The primary limitation in my screen was using bWAR3, aka, the cumulative bWAR over the 3 seasons prior to the player hitting free agency. It is not an outcome metric, as I was looking at the 3 seasons prior to the free agent signing, not any subsequent signings. It was instead intended to be used as an imperfect guide to the most prominent free agents that particular offseason. But that metric does have its limitations, many of which you noted. Let me try to address the points you raised:

- Carl Pavano was the prize in the 2004-05 offseason, and Theo was in on him. He's omitted in your year-by-year breakdown. As a fan of the team, I'm glad it didn't work out, but the Sox whiffing on him while letting Pedro and Lowe walk meant they needed to make up 400 innings quick, which led them to go after Clement.
Obviously, the big prize that offseason was Pedro: 19.8 combined bWAR from 2002-04. The Sox lost out on him, but that had nothing to do with Fenway Park, but instead was because the Mets were willing to offer a 4th guaranteed year, something Theo was unwilling to do (and for good reason, as it turned out). Carl Pavano got a big ticket contract, but his bWAR3 at the time of his signing was 7.3, which was less than my cutoff of 9.0, mainly because of his crappy 2002.

- Why is Smoltz counted here as a major free agent signing? He wasn't a coveted free agent, he was a late-career/scrap heap flyer that didn't work out. Same with Wade Miller, Brad Penny, Bartolo Colon, Doug Fister, Paul Byrd, etc. I think those guys are somewhat outside the scope.
Another limitation to my screen. Smoltz was very good in 2006 and 2007, and was pretty effective until he got hurt in 2008. So his bWAR3 met the criteria I was using.

- Why are we counting Schilling — a guy the Sox traded for — re-upping with the team on a couple one-year deals and not counting, say, Eovaldi? I think it definitely *is* common practice for the Sox to trade for a guy and then try to sign or extend him (Schilling, Porcello, Beckett, Eovaldi, Pedro). The Cardinals often do this too (see Paul Goldschmidt), and like to see that a player fits with their climate. This seems necessary for a pressure-cooker city like Boston.
I mentioned I was breaking out re-signings separately, so you're free to ignore them. And Schilling was yet another illustration of some of the limitations of the screen I was using. He was very good in 2006 and 2007. Of course, turns out he was injured when he resigned, but noone knew that at the time. Note that he was only counted once in this analysis; his extensions which were signed prior to his becoming a free agent were ignored.

Eovaldi came nowhere near meeting the screen, given that he missed all of 2017, and was average in 2015 and 2016.

- The Dodgers, to take one team in your list, have signed well more than *three* free agents over that time. Jason Schmidt was a huge one; he just got hurt. Others that fit your criteria off the top of my head include McCarthy, Greinke, Wolf, Capuano, Kazmir, Ryu, Kuroda, Rich Hill, Aaron Harang, Ted Lilly, and Derek Lowe. They also spent big money extending Kershaw, Billingsley, and Brad Penny. You have the Giants signing two guys, but from memory they've signed Cueto, Samardzija, Zito, Hudson, Matt Morris, Vogelsong, et al. over that period.
Again, I was focusing on guys that had #1/1A starter records. I mentioned how Greinke barely missed the cut. I counted Lowe. And I ignored extensions. Most of the players you mentioned for the Dodgers missed the cut, as they were considered good, but not premier free agent starters. As for the Giants, I counted Cueto and Zito. Samardzija had one good year (2014) prior to his 2016 free agency. Tim Hudson's best days were way past him, and he was basically average in his final couple of seasons with the Braves. Matt Morris and Vogelsong weren't even average prior to joining the Giants, and so weren't exactly highly sought after.

- Is it really helpful to compare the Sox' ability to sign FA pitchers compared to small market teams like the Marlins, Tigers and Padres? Ironically, I think it was reported that Theo [edit: Cherington] lost out to the Marlins on Buehrle in 2012, but typically those teams have wildly different contention cycles, budgets and business models and are not pulling from the same pool.
Other posters here think Florida or California teams have a significant advantage, so I couldn't really exclude them. But even among big market teams, Boston has had no trouble getting premier free agents when they were aggressive. Not all pursuits succeeded, but that is true of every single team; no team is batting 1.000.

I guess I could expand my criteria at some point. As I noted, free agent pitchers come in all sorts of shapes and sizes, and there are many ways to build a championship pitching staff, something the Red Sox have done 4 times recently. But any screen will be somewhat arbitrary.
 

lexrageorge

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I remember that before Schilling came here, Boston had a hard time getting free agent pitchers. He was the guy who flipped the script a little bit (even though he came in via trade, he had a NTC and it was similar to courting a FA.)

In the 2000 offseason, the Red Sox main free agent target was actually Mike Mussina. The main hangup was that he wanted a NTC, but also I think the stigma of pitching in Fenway was part of why he chose the MFY offer. It all worked out because Manny was the more valuable player, and he won two rings in Boston (compared to Moose's 0 rings in New York) but I remember that being more evidence that free agent pitchers didn't want to come here.
The interesting aspect is that the Sox aggressively pursued Mussina precisely because he was used to pitching in the AL East and has success in both Fenway and Yankee Stadium. Mussina also wanted a ring, and the Yankees were coming off a stretch of winning the Series 4 of the past 5 seasons.

The years prior to 2004 were interesting. In 1991 and 1992, the Sox signed one of the top free agents available in that period in Frank Viola, and paid another two like they were premium free agents in both Danny Darwin and the horrific Matt Young. Things got kind of wonky after that. Their only free agent starter pitcher signings of any note after that were Tom Gordon; Jeff Fassero; Brother Ramon (who was a scrap heap signing as he was injured); Brett Saberhagen (ditto); a 38 y/o David Cone, whom IIRC they had tried to sign years earlier but were rebuffed in favor of the Yankees; Hideo Nomo (more of a lottery ticket at the time), and the embedded Yankee (who was a reliever). Many of those guys were not really pursued by their previous team aside perhaps from the player who graces the title of a Steven King novel. But there were a lot of other issues with the team at the time, which have long since been put to bed, so it's probably not really relevant anymore.
 

wade boggs chicken dinner

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The interesting aspect is that the Sox aggressively pursued Mussina precisely because he was used to pitching in the AL East and has success in both Fenway and Yankee Stadium. Mussina also wanted a ring, and the Yankees were coming off a stretch of winning the Series 4 of the past 5 seasons.

The years prior to 2004 were interesting. In 1991 and 1992, the Sox signed one of the top free agents available in that period in Frank Viola, and paid another two like they were premium free agents in both Danny Darwin and the horrific Matt Young. Things got kind of wonky after that. Their only free agent starter pitcher signings of any note after that were Tom Gordon; Jeff Fassero; Brother Ramon (who was a scrap heap signing as he was injured); Brett Saberhagen (ditto); a 38 y/o David Cone, whom IIRC they had tried to sign years earlier but were rebuffed in favor of the Yankees; Hideo Nomo (more of a lottery ticket at the time), and the embedded Yankee (who was a reliever). Many of those guys were not really pursued by their previous team aside perhaps from the player who graces the title of a Steven King novel. But there were a lot of other issues with the team at the time, which have long since been put to bed, so it's probably not really relevant anymore.
Going from memory here so I might be wrong but wasn't the Duke's eternal quest to find lighting in a bottle due mostly to budgetary concerns?
 

Yelling At Clouds

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The interesting aspect is that the Sox aggressively pursued Mussina precisely because he was used to pitching in the AL East and has success in both Fenway and Yankee Stadium. Mussina also wanted a ring, and the Yankees were coming off a stretch of winning the Series 4 of the past 5 seasons.

The years prior to 2004 were interesting. In 1991 and 1992, the Sox signed one of the top free agents available in that period in Frank Viola, and paid another two like they were premium free agents in both Danny Darwin and the horrific Matt Young. Things got kind of wonky after that. Their only free agent starter pitcher signings of any note after that were Tom Gordon; Jeff Fassero; Brother Ramon (who was a scrap heap signing as he was injured); Brett Saberhagen (ditto); a 38 y/o David Cone, whom IIRC they had tried to sign years earlier but were rebuffed in favor of the Yankees; Hideo Nomo (more of a lottery ticket at the time), and the embedded Yankee (who was a reliever). Many of those guys were not really pursued by their previous team aside perhaps from the player who graces the title of a Steven King novel. But there were a lot of other issues with the team at the time, which have long since been put to bed, so it's probably not really relevant anymore.
Technically, Duquette did sign Kevin Appier at one point. And Sammy Sosa!
 

Sandy Leon Trotsky

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Going from memory here so I might be wrong but wasn't the Duke's eternal quest to find lighting in a bottle due mostly to budgetary concerns?
I don't recall any serious budgetary concerns... just general frustration that he never got a compliment to Pedro. Until Derek Lowe's '02 season, it was pretty much Pedro and a bunch of "no. 3's" at best. Lowe's '03 was just okay. By '04 Pedro's best years were clearly behind him and he sort of filled in as the ace.2 behind Schilling. Anyhow... I was always just so frustrated with that and when Mussina turned down the Sox offer to go to NY I thought it was pretty much a done deal that they were never going to go the extra mile to put a great team together
 

chawson

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Some posters here think Florida or California teams have a significant advantage, so I couldn't really exclude them. But even among big market teams, Boston has had no trouble getting premier free agents when they were aggressive. Not all pursuits succeeded, but that is true of every single team; no team is batting 1.000.

I guess I could expand my criteria at some point. As I noted, free agent pitchers come in all sorts of shapes and sizes, and there are many ways to build a championship pitching staff, something the Red Sox have done 4 times recently. But any screen will be somewhat arbitrary.
Isn’t it common knowledge that the Rockies have difficulty luring free agent pitchers to play in that dong carnival of a park? Why is it hard to think the Sox, who consistently rank second or third in MLB in park factors for offense, face a similar (if lesser) obstacle?

One thing I’m not wild about in your metric is that it excludes the 2/$10-20 million type contracts which Boston almost never signs. Sometimes these guys are simply middling and we don’t want them anyway. Sometimes they sign elsewhere because they want to rebuild value, and no sensible pitcher would try to do that in Fenway. But sometimes those guys just sign elsewhere. Those kinda guys can have value in rounding out a rotation, and Burkett and Wells are the only examples this century (I’ve really only been looking 2000 on).

Premier free agents are typically bid up to the point where they land with major-market teams. I don’t see how you can look at even your own metric and conclude that “Boston has had no trouble getting premier free agents when they were aggressive.” I think the way to do it is to look at, say, the top 25 free agents by contract $ since 2000, and then compare the starting pitchers the Sox signed against the ones signed by other major-market teams with top 10 payrolls (which is a lot of work, and I’m not suggesting you do).
 

Plympton91

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It was definitely the visionless John Harrington who constantly tried to make the Red Sox into a mid-market team and kept the financial shackles on during the Duquette years. The epitome of penny wise and pound foolish, Harrington was always setting the budget at what would have been sufficient to win in the prior year, and thus actually saving money in the long run. But no.

And so, as Sandy Leon trotsky said, the 1998-2001 Sox were perpetually a #2 starter and a middle of the order bat away from getting by the Yankees. Instead of getting a real solution, Duke was left trying to put together those pieces with Saberhagen’s bionic arm and later replacing Mo Vaughn a year too late with the clinically insane and thus less expensive Carl Everett.

Good times. Good times.
 

lexrageorge

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Isn’t it common knowledge that the Rockies have difficulty luring free agent pitchers to play in that dong carnival of a park? Why is it hard to think the Sox, who consistently rank second or third in MLB in park factors for offense, face a similar (if lesser) obstacle?

One thing I’m not wild about in your metric is that it excludes the 2/$10-20 million type contracts which Boston almost never signs. Sometimes these guys are simply middling and we don’t want them anyway. Sometimes they sign elsewhere because they want to rebuild value, and no sensible pitcher would try to do that in Fenway. But sometimes those guys just sign elsewhere. Those kinda guys can have value in rounding out a rotation, and Burkett and Wells are the only examples this century (I’ve really only been looking 2000 on).

Premier free agents are typically bid up to the point where they land with major-market teams. I don’t see how you can look at even your own metric and conclude that “Boston has had no trouble getting premier free agents when they were aggressive.” I think the way to do it is to look at, say, the top 25 free agents by contract $ since 2000, and then compare the starting pitchers the Sox signed against the ones signed by other major-market teams with top 10 payrolls (which is a lot of work, and I’m not suggesting you do).
When I used my admittedly imperfect metric, the Sox had signed as many if not more premier free agent starters as any other big market team. Price and Lackey were the two premier free agent pitchers during their respective offseasons. The Sox aggressively pursed both and got them. It doesn't make sense to discount those signings as others have done.

I would like to expand my sample size (41 pitchers is not a lot), and filter by contract, and consider those mid-rotation pitchers as well. Probably will not get to that for a while.
 

Cesar Crespo

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It was definitely the visionless John Harrington who constantly tried to make the Red Sox into a mid-market team and kept the financial shackles on during the Duquette years. The epitome of penny wise and pound foolish, Harrington was always setting the budget at what would have been sufficient to win in the prior year, and thus actually saving money in the long run. But no.

And so, as Sandy Leon trotsky said, the 1998-2001 Sox were perpetually a #2 starter and a middle of the order bat away from getting by the Yankees. Instead of getting a real solution, Duke was left trying to put together those pieces with Saberhagen’s bionic arm and later replacing Mo Vaughn a year too late with the clinically insane and thus less expensive Carl Everett.

Good times. Good times.
DD also wasted a lot of money on middling players like Dante Bichette, Jose Offerman and Mike Lansing, even if the Lansing deal was to find the "bargain" of Rolando. Maybe those deals were DD trying to find a bargain, but he overpaid for all of them.

Then Epstein came in and found real bargains like Bill Mueller, Bronson, Ortiz, etc. Not Mike Lansing at $7 mil a year.
 

Red(s)HawksFan

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Isn’t it common knowledge that the Rockies have difficulty luring free agent pitchers to play in that dong carnival of a park? Why is it hard to think the Sox, who consistently rank second or third in MLB in park factors for offense, face a similar (if lesser) obstacle?

One thing I’m not wild about in your metric is that it excludes the 2/$10-20 million type contracts which Boston almost never signs. Sometimes these guys are simply middling and we don’t want them anyway. Sometimes they sign elsewhere because they want to rebuild value, and no sensible pitcher would try to do that in Fenway. But sometimes those guys just sign elsewhere. Those kinda guys can have value in rounding out a rotation, and Burkett and Wells are the only examples this century (I’ve really only been looking 2000 on).

Premier free agents are typically bid up to the point where they land with major-market teams. I don’t see how you can look at even your own metric and conclude that “Boston has had no trouble getting premier free agents when they were aggressive.” I think the way to do it is to look at, say, the top 25 free agents by contract $ since 2000, and then compare the starting pitchers the Sox signed against the ones signed by other major-market teams with top 10 payrolls (which is a lot of work, and I’m not suggesting you do).
Coors is so far and away the most hitter-friendly park that it's not even comparable to the rest. Fenway is hitter friendly, but it is far closer to other, more pitcher friendly parks than it is to Coors. Close enough that I don't think it enters into the equation for most free agents.

I disagree with the idea of simply looking at the premier free agents that landed big contracts, counting how many the Red Sox signed, and drawing conclusions. First, can you really say the player spurned the Red Sox, for park or other reasons, if they never really made a serious pursuit? For the better part of 15 years, the Red Sox front office was run by guys (Theo, Cherington) who thought the free agent market was an inefficient means to acquire top talent, pitching or otherwise. I just don't see how to draw conclusions that, for example, Barry Zito (biggest FA pitching contract ever at the time) didn't sign in Boston because he didn't want to play here as opposed to Theo never made a serious offer. He had signed Matsuzaka for a lesser total package and already had Beckett, Schilling, Wakefield, Tavarez, Lester, and other young pitchers like Buchholz, Masterson, Bowden (all on BA top 100 pre-2007), Hansack, and Gabbard in the pipeline. That was the peak of the "player development machine" Theo wanted.

By that same token, hard to draw much of a conclusion from the lack of "middling" signings since, again, the team wasn't often hard-up for pitching. They had vets, trade acquisitions, and they had a pipeline of young guys as well. Perhaps they weren't signing those types because they didn't think they needed them rather than that those pitchers chose to stay away. That said, you missed a few pitchers from your list. It was far more than just Burkett and Wells based on your criteria. I think you're overlooking (working backwards) Masterson (1/10), Dempster (2/26), Penny (1/5), Smoltz (1/5...if you're counting Wells, have to count Smoltz).
 

chawson

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Coors is so far and away the most hitter-friendly park that it's not even comparable to the rest. Fenway is hitter friendly, but it is far closer to other, more pitcher friendly parks than it is to Coors. Close enough that I don't think it enters into the equation for most free agents.
You're right that Coors is (typically) far and away the most hitter-friendly park. But Fenway is routinely Top 5. It's the most hitter-friendly park of the big-market teams, generally. We also have the evidence that Schilling stated 15 years ago he didn't think he would fare well at Fenway, which could be seen as proof that there's a narrative that pitchers believe things like this.

I disagree with the idea of simply looking at the premier free agents that landed big contracts, counting how many the Red Sox signed, and drawing conclusions. First, can you really say the player spurned the Red Sox, for park or other reasons, if they never really made a serious pursuit? For the better part of 15 years, the Red Sox front office was run by guys (Theo, Cherington) who thought the free agent market was an inefficient means to acquire top talent, pitching or otherwise. I just don't see how to draw conclusions that, for example, Barry Zito (biggest FA pitching contract ever at the time) didn't sign in Boston because he didn't want to play here as opposed to Theo never made a serious offer. He had signed Matsuzaka for a lesser total package and already had Beckett, Schilling, Wakefield, Tavarez, Lester, and other young pitchers like Buchholz, Masterson, Bowden (all on BA top 100 pre-2007), Hansack, and Gabbard in the pipeline. That was the peak of the "player development machine" Theo wanted.
Addressing the bolded in order: 1. No, we can't. We don't have access to that information. 2. Yeah, that's fair, and it is. But the Sox are a big payroll team and should be able, like the Dodgers, Cubs, Yankees, Mets, Giants, and Phillies, to spend some money to fill rotation holes. They have, but they haven't as much as those teams, not over the last 15-20 years anyway. 3. Zito is a fairly pointed example, since everyone on this board knew Theo was smart enough not to sign him. 4. They "already had" Beckett and Schilling because they traded for them. Wakefield is a true anomaly here, and I think his presence probably did protect the FO from dropping money in the free agent market for a decade. Tavarez was signed as a reliever and only made 23 starts. Masterson made 15 before being traded. Gabbard made 11 starts before Theo sold high. Bowden made two. Hansack made three, two of them in the final week of a lost season. The "player development machine" really only produced Lester and Buchholz (and Doubront, I guess).

By that same token, hard to draw much of a conclusion from the lack of "middling" signings since, again, the team wasn't often hard-up for pitching. They had vets, trade acquisitions, and they had a pipeline of young guys as well. Perhaps they weren't signing those types because they didn't think they needed them rather than that those pitchers chose to stay away. That said, you missed a few pitchers from your list. It was far more than just Burkett and Wells based on your criteria. I think you're overlooking (working backwards) Masterson (1/10), Dempster (2/26), Penny (1/5), Smoltz (1/5...if you're counting Wells, have to count Smoltz).
Yep, I cited all those guys in the Sale IL thread before the conversation broke out to this new one. I had wrongly remembered Dempster's original contract as a three-year deal that was voided after a year, but you're right that it was 2/$26.
 

Red(s)HawksFan

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Addressing the bolded in order: 1. No, we can't. We don't have access to that information. 2. Yeah, that's fair, and it is. But the Sox are a big payroll team and should be able, like the Dodgers, Cubs, Yankees, Mets, Giants, and Phillies, to spend some money to fill rotation holes. They have, but they haven't as much as those teams, not over the last 15-20 years anyway. 3. Zito is a fairly pointed example, since everyone on this board knew Theo was smart enough not to sign him. 4. They "already had" Beckett and Schilling because they traded for them. Wakefield is a true anomaly here, and I think his presence probably did protect the FO from dropping money in the free agent market for a decade. Tavarez was signed as a reliever and only made 23 starts. Masterson made 15 before being traded. Gabbard made 11 starts before Theo sold high. Bowden made two. Hansack made three, two of them in the final week of a lost season. The "player development machine" really only produced Lester and Buchholz (and Doubront, I guess).
My point in listing all those pitchers wasn't to say that they were all successes of the "player development machine" so much as to say that, at the time (winter 06-07), there was plenty of starting pitching depth in the organization. Such that signing a free agent to a long term deal, or in that case two after DiceK, wasn't really in the best interests of the club. Whether it was Zito or someone else (better), I have my doubts that Theo would have been in all that hot of a pursuit on that free agent market.

There's no denying that the Red Sox are a big market team. But just because they have financial clout doesn't mean they have to be in on every high priced free agent on the market every winter. That they haven't made a big splash on the free agent market as often as other teams doesn't mean they're less attractive to the players. As I've been trying to say, it's an organizational philosophy more than anything else. When you aim to create a player development machine, you're doing it for two reasons...1) to develop top flight talent in-house and 2) to have prospect capital to make trades for what you need.
 

BeantownIdaho

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Petey retiring would help the club moving forward. Retire....hire as a bench coach at his same salary or something comparable with incentives/bonus/etc.....free up 13+ million.
 

uncannymanny

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You're right that Coors is (typically) far and away the most hitter-friendly park. But Fenway is routinely Top 5. It's the most hitter-friendly park of the big-market teams, generally. We also have the evidence that Schilling stated 15 years ago he didn't think he would fare well at Fenway, which could be seen as proof that there's a narrative that pitchers believe things like this.
If you look deeper into the PF numbers, it’s not a hugely hitter friendly park. It’s a great doubles park, ESPECIALLY for LHB.

https://www.fangraphs.com/guts.aspx?type=pfh&season=2018&teamid=0&sort=4,d
 

nvalvo

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Petey retiring would help the club moving forward. Retire....hire as a bench coach at his same salary or something comparable with incentives/bonus/etc.....free up 13+ million.
People need to stop inventing cockamamie schemes to get around our CBT threshold situation. The league shouldn't let us get away with that, and they won't.

It might be an interesting question for a future CBA. What if each team got one slot at a time for a deal that had gone sideways; say, in exchange for removing some portion of the player's salary from the CBT number, the player would get paid but could not be rostered again by any team during the duration of the contract — both the team and player would have to agree to do this. So we'd use ours on Pedroia, but then we couldn't do it again until his deal was up. If *knocks on wood* *burns incense* *mutters the names of several saints* someone else had a career-ending injury while Pedroia was in that slot, we'd still be SOL.

This would be useful to teams in scenarios like Prince Fielder had. This would be desirable for the players because it would mitigate the risks of the kinds of high-dollar, long-term guaranteed contracts they want teams to be extending.

But you couldn't use it on a guy like Sandoval, because he wasn't done playing.
 
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People need to stop inventing cockamamie schemes to get around our CBT threshold situation. The league shouldn't let us get away with that, and they won't.

It might be an interesting question for a future CBA. What if each team got one slot at a time for a deal that had gone sideways; say, in exchange for removing some portion of the player's salary from the CBT number, the player would get paid but could not be rostered again by any team during the duration of the contract — both the team and player would have to agree to do this. So we'd use ours on Pedroia, but then we couldn't do it again until his deal was up. If *knocks on wood* *burns incense* *mutters the names of several saints* someone else had a career-ending injury while Pedroia was in that slot, we'd still be SOL.

This would be useful to teams in scenarios like Prince Fielder had. This would be desirable for the players because it would mitigate the risks of the kinds of high-dollar, long-term guaranteed contracts they want teams to be extending.

But you couldn't use it on a guy like Sandoval, because he wasn't done playing.
The purpose of the luxury tax is to allow the smaller market teams to be more competitive. Your scheme would widen the the gap between the haves and the have nots.