Worst Red Sox contracts ever

Van Everyman

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Not for nothing, but an aside about Carl Crawford.

He's now a music executive, and he signed Megan Thee Stallion -- if you don't know who Megan is, she's one of ten greatest female rappers of all time. He's also essentially holding her hostage on his label and she's called him a "powder head", which implies exactly what you think it implies.

He signed her to a predatory 360 deal early in her career, and she blew up well beyond anyone's initial expectations. And now... they are suing one another.

https://afrotech.com/megan-thee-stallion-carl-crawford-lawsuit?item=2
This seems like a nice gentleman’s dispute:

Later in the evening Monday, Megan Thee Stallion then proceeded to call out Crawford directly, even accusing him of drug use.

“Carl I don’t wanna be signed to yo pill popping ass!” she tweeted. “You talking abt I ain’t paid for a show and you sound slow. I’m the artist I don’t pay you directly maybe fight with THE MAN YOU SIGNED TO AND YOU MIGHT SEE SOME MONEY YOU F–KING POWDER HEAD! You hiding behind [Rap-A-Lot records CEO] JPRINCE.”

Crawford addressed Megan The Stallion in an Instagram post on Monday, writing: “Stop playing the victim @theestallion u haven’t paid for 1 show since 2019 hiding behind #Rocnation .. U can keep that bulls–t ass mix tape and send over that straight drop whenever u read.”
https://nypost.com/2022/03/22/megan-thee-stallion-calls-carl-crawford-powder-head-in-contract-feud/
 

Shaky Walton

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Don't sleep on, or with, Rusney Castillo. The Sox signed him in August, 2014 for $72.5 mm.

Castillo put up good numbers, albeit in short seasons, in Cuba in 2010-11and 2011-12. He then saw his numbers decline -- his batting average was .274 for example -- in 2012-13 and he missed almost all of 2013-2014 until the Sox signed him due to injury.

So off a few strong seasons in Cuba, which is effectively a AAA comp, and a down year and a year in which he didn't play, the Red Sox gave him an enormous contract.

Trying to catch the Cuban wave or some such thing.

We all saw the results and his inability to stick with the team.

At least guys like Sandoval and Crawford had enjoyed some success in the majors and at least whatever success they did enjoy wasn't so limited.

His numbers:

https://www.baseball-reference.com/register/player.fcgi?id=castil000rus
 

m0ckduck

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It's no Panda or Rusney by a long shot, but: resigning Mike Lowell heading into 2008 went pretty badly: 3/37M for 2.1 bWar overall, and negative value the last two seasons. That deal had the weird quality of being clearly bad at the time and yet nobody could bring themselves to care, since he'd just taken home the WS MVP.
 

jose melendez

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It's got to be something recent, because the contracts were just so much shorter back in the day. An 8 year mistake is so much worse than a three year mistake.

What about non-contracts--can we add Fisk?
 

lexrageorge

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Me too, with Sandoval a close second.

It was clear before the ink was dry that signing Price was in lieu of keeping at least one of our young stars. That puts it ahead of Sandoval, which was a worse talent evaluation (he was declining his last two years in SF, and the Giants couldn’t wait to be rid of him), but Panda got less than half as many total dollars as Price and therefore didn’t hamstring us nearly as much.
Price played a huge role in the Red Sox 2018 run and title, so his contract is IMO disqualified from being among the worst.
 

moondog80

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Price played a huge role in the Red Sox 2018 run and title, so his contract is IMO disqualified from being among the worst.
Price also gave us 588 IP with an ERA+ of 118. He’s not in the top 10.

Sandoval’s most productive year was 2016 when he only had 7 PA and thus very little opportunity to be below replacement level. It wasn’t a mega-deal like some others, but he was never an even marginally productive player.
 

mauf

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Price played a huge role in the Red Sox 2018 run and title, so his contract is IMO disqualified from being among the worst.
I’m not sure how to think about that. Price’s postseason results were excellent, but with 10 unintentional walks in 24 innings, wasn’t he more lucky than good? His regular-season results were solid, but weren’t among the 10 biggest reasons that team was special. I wouldn’t trade the 2018 title to still have Mookie Betts on the team*, but I think they probably win without Price, especially if you assume his money was redeployed in some way.

I’ll cheer Price when he comes back to Fenway someday, but I’m still inclined to view the signing as a mistake, both ex ante and ex post.


*- Yes, I’m aware there’s a good chance Mookie didn’t want to be here beyond 2020 in any event, and Chaim might not have met his price even if he had the money to spend.
 

lexrageorge

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I’m not sure how to think about that. Price’s postseason results were excellent, but with 10 unintentional walks in 24 innings, wasn’t he more lucky than good? His regular-season results were solid, but weren’t among the 10 biggest reasons that team was special. I wouldn’t trade the 2018 title to still have Mookie Betts on the team*, but I think they probably win without Price, especially if you assume his money was redeployed in some way.

I’ll cheer Price when he comes back to Fenway someday, but I’m still inclined to view the signing as a mistake, both ex ante and ex post.


*- Yes, I’m aware there’s a good chance Mookie didn’t want to be here beyond 2020 in any event, and Chaim might not have met his price even if he had the money to spend.
6 of those walks were in the first 2 games: one dreadful outing against New York, and one mediocre start against the Trash Cans. But he was outstanding in Game 5 against Houston, and put together 2 very solid starts against the Dodgers, and it's revisionist history to downgrade either of those 2 World Series starts The starting pitching was a bit thin in the post season, and it's conceivable if Price was not there that the Sox could have lost.

From a roster management and payroll perspective, sure, it's conceivable that the same money could have been redeployed and they win anyway. But there's also an excellent chance that the hypothetical other players do not match up to what Price contributed in 2018. Overall, Price really was a very good pitcher for the team in 2016 and 2018. He battled injuries in 2017 and 2019, and that seems to be what most people here remember. And his bad playoff start against Cleveland in 2016.
 

BuellMiller

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He was actually pretty decent his first year in Boston. 826 OPS, 108 OPS+ at 2B. Made the All-Star Team!

Was dreadful after that.
His 2000 season had some bit of BABIP bad luck involved (going from around .320 in his previous several years to like .280), but still walked a bit. He did go from stealing 45 bases in his final season in KC to 18 in 1999 to going 0 for 8 in 2000, so maybe there was also a bit of decline in athletic ability (either from age, injury, or not giving an f after signing).
Some of the disregard of his contract at the time was the loss of Mo at the same time (although, in hindsight that was a missed bullet to some degree), as well as missing out of Bernie Williams (whether he would have actually signed or was just potential interest to get more $ from the MFY). Also, in hindsight, whether they could have better spent that money they spent on Offerman on Robbie Alomar instead (signed later in that offseason for a few million more), but not sure if they were ever actively in on him or considered him.
 

John Marzano Olympic Hero

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Hard to gauge from a monetary standpoint because the money was so different back then, but Lou Gorman had a long, long list of bad contract detritus on his ledgers. It's kinda incredible how many free agents he signed that were a) in their mid-30s and b) were more or less the highlight acquisitions of those winters: Dennis Lamp (35), Tony Pena (33), Jeff Reardon (34), Matt Young (32), Jack Clark (35), Danny Darwin (35), Frank Viola (32), and finally Dawson (38). However much these guys were paid, being past their prime almost guaranteed they'd be viewed as disappointments.
I'm glad you listed all of these players out because it never occurred to me how old they all were when Gorman signed them. All of them were so far beyond the primes and most of them just broken down.

Gorman severely lost his fastball as an executive after 1986. Trades, scouting, signing free agents; he just hit a wall.
 

Red(s)HawksFan

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I'm glad you listed all of these players out because it never occurred to me how old they all were when Gorman signed them. All of them were so far beyond the primes and most of them just broken down.

Gorman severely lost his fastball as an executive after 1986. Trades, scouting, signing free agents; he just hit a wall.
It occurred to me as I was looking up those players that perhaps they were all older because players hit free agency later on average than they do now, but even still, he never seemed to go after the cream of the crop. As an example, when the Red Sox signed Dawson (2 years!!! for ~$9M), these were some of the notables who signed with new teams that winter: Greg Maddux (27), Barry Bonds (28), Benito Santiago (28), Ellis Burks (28), David Cone (30), Jose Guzman (30), Chris Bosio (30), Jimmy Key (32), Chili Davis (33), Mike Moore (33), Wade Boggs (35), Tom Henke (35), Dave Stewart (36), Dave Winfield (41), Charlie Hough (45).
 

John Marzano Olympic Hero

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It occurred to me as I was looking up those players that perhaps they were all older because players hit free agency later on average than they do now, but even still, he never seemed to go after the cream of the crop. As an example, when the Red Sox signed Dawson (2 years!!! for ~$9M), these were some of the notables who signed with new teams that winter: Greg Maddux (27), Barry Bonds (28), Benito Santiago (28), Ellis Burks (28), David Cone (30), Jose Guzman (30), Chris Bosio (30), Jimmy Key (32), Chili Davis (33), Mike Moore (33), Wade Boggs (35), Tom Henke (35), Dave Stewart (36), Dave Winfield (41), Charlie Hough (45).
It was strange, for a team that made a big splash in the first free agent winter (Bill Campbell), it didn't seem like the Red Sox really understood free agency until the signed Manny. They kinda loped around and kicked a few tires, they were used as the mystery team so that stars (Kirby Puckett and Bernie Williams are two that I know about) could have leverage with their old teams and then they would sign all of these past-their-prime former stars to fill key roles. And it never worked. I couldn't figure out if the Red Sox were being cheap or stupid.
 

Red(s)HawksFan

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It was strange, for a team that made a big splash in the first free agent winter (Bill Campbell), it didn't seem like the Red Sox really understood free agency until the signed Manny. They kinda loped around and kicked a few tires, they were used as the mystery team so that stars (Kirby Puckett and Bernie Williams are two that I know about) could have leverage with their old teams and then they would sign all of these past-their-prime former stars to fill key roles. And it never worked. I couldn't figure out if the Red Sox were being cheap or stupid.
I'm going with stupid if only because they did spend money. Gorman made Clemens one of the highest paid players in the league from 1991-96. He gave Dawson nearly about $4.5M per year at a time when the highest paid player in the game was getting just about $6M (Bobby Bonilla). He spent money, just on a lot of the wrong players.

Duquette also spent money, even before Manny (the extensions to Pedro and Nomar were rich for the time). But he seemed to revel in being the smart guy finding value before it was the cool thing so you get instances like Clemens and Vaughn walking away because the Sox wouldn't pay up, as well as Pedro and Nomar being surrounded by journeyman and broken down vets and prospects instead of more high quality players. I think it was only fear for his job because of the pending sale that Duquette abandoned the "value" approach and splashed for Manny (after striking out on Mussina), and then Damon a year later.
 

Van Everyman

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It occurred to me as I was looking up those players that perhaps they were all older because players hit free agency later on average than they do now, but even still, he never seemed to go after the cream of the crop. As an example, when the Red Sox signed Dawson (2 years!!! for ~$9M), these were some of the notables who signed with new teams that winter: Greg Maddux (27), Barry Bonds (28), Benito Santiago (28), Ellis Burks (28), David Cone (30), Jose Guzman (30), Chris Bosio (30), Jimmy Key (32), Chili Davis (33), Mike Moore (33), Wade Boggs (35), Tom Henke (35), Dave Stewart (36), Dave Winfield (41), Charlie Hough (45).
For that reason, Duke's signing of Manny at 160/8 felt like such a sea change: the Sox getting a premium free agent in the prime of his career. The best Red Sox contract ever?

Edit: @Red(s)HawksFan juuuuuust beat me to it. But Manny really was the dividing line, it felt like.
 

lexrageorge

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It was strange, for a team that made a big splash in the first free agent winter (Bill Campbell), it didn't seem like the Red Sox really understood free agency until the signed Manny. They kinda loped around and kicked a few tires, they were used as the mystery team so that stars (Kirby Puckett and Bernie Williams are two that I know about) could have leverage with their old teams and then they would sign all of these past-their-prime former stars to fill key roles. And it never worked. I couldn't figure out if the Red Sox were being cheap or stupid.
The Mike Torrez signing was a big splash the following offseason. His 1977 postseason performance was rightfully overshadowed by Reggie Jackson's heroics, but if not for his crucial relief stint in the clinching game of the ALCS, there is no Mr. October.

The Sox, especially in the early 1980's, managed themselves much like a small market team. Players were regularly traded before they hit free agency when Haywood Sullivan ran the team. There were ownership struggles as well; recall Buddy LeRoux's disgraceful coup attempt on Tony C night. There were even rumors that the owners were looking to sell the team to out of town owners with a possible relocation in mind.

And, to be fair, when Lou Gorman was hired on, he did focus on rebuilding a barren farm system, which bore fruit in 1986 and helped them further in the latter part of the 80's. Thanks to collusion among the MLB owners (Sox included), there was very little player movement during the mid-1980's. And there was always some drama; they lost Bruce Hurst to free agency because they toed the league line on the lockout language, a trend which hurt them throughout the early 90's as well. It was part of the reason why Gorman had to overpay for the 2nd tier free agents like Danny Darwin or Matt Young or Otis Nixon or Andre Dawson. Boston just wasn't a destination for the premier players, and a lot of players, especially Black players, routinely would place Boston on their no-trade lists.

They did start to flex their financial muscle a bit when Duquette came on board, but he also was dealing with a barren farm system. The Manny signing was huge, but should also point out that he was their 2nd choice after they heavily pursued Mike Mussina and lost out to the Yankees. And Theo & Co were trying to find ways to move on from Manny's contract early on, either by placing him on irrevocable waivers or by attempting to move him for A-Rod.

Anyway, for those of us that lived through the pre-Henry owners, there is zero doubt that we as fans lucked out with the current ownership team.
 

cornwalls@6

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It was strange, for a team that made a big splash in the first free agent winter (Bill Campbell), it didn't seem like the Red Sox really understood free agency until the signed Manny. They kinda loped around and kicked a few tires, they were used as the mystery team so that stars (Kirby Puckett and Bernie Williams are two that I know about) could have leverage with their old teams and then they would sign all of these past-their-prime former stars to fill key roles. And it never worked. I couldn't figure out if the Red Sox were being cheap or stupid.
They really were lost in the weeds. On the cheap front, with a possible ulterior motive. IIRC, one of the main justifications they had for wanting a new ballpark built was to have the revenue to attract/retain top free agents. Signing them on any kind of regular basis would undermine that argument. But to your broader point, agree completely. There was more than a little bit of stupid and incompetence at play, and they spent the better part of 20 years failing to understand the process, and how to get value out of of it. The Duke got them started on the road(but of course, forever has the blood of Jose Offerman on his hands), but it really took Theo to start becoming big, smart players in free agency.
 

BaseballJones

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The Castillo deal is and forever will be hilarious. They gave him a ton and yet it was worth more to them to pay him that much to stick in AAA, because it would have hurt the team far more to have him on the MLB roster. I don't think I've ever seen anything like that in sports before.
 

John Marzano Olympic Hero

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Can’t it be both?
It certainly can, but I was being diplomatic.

I'm going with stupid if only because they did spend money. Gorman made Clemens one of the highest paid players in the league from 1991-96. He gave Dawson nearly about $4.5M per year at a time when the highest paid player in the game was getting just about $6M (Bobby Bonilla). He spent money, just on a lot of the wrong players.

Duquette also spent money, even before Manny (the extensions to Pedro and Nomar were rich for the time). But he seemed to revel in being the smart guy finding value before it was the cool thing so you get instances like Clemens and Vaughn walking away because the Sox wouldn't pay up, as well as Pedro and Nomar being surrounded by journeyman and broken down vets and prospects instead of more high quality players. I think it was only fear for his job because of the pending sale that Duquette abandoned the "value" approach and splashed for Manny (after striking out on Mussina), and then Damon a year later.
Like I said, it seems to me Gorman lost his fastball and was just throwing money at names because that's what sells tickets in the winter. While the Duke was the prototype for the dumpster diving GMs, who loved finding value in other teams' throwaways. And I think that works to an extent. For every Troy O'Leary there's two Midre Cummings. For every Tim Wakefield, there's a dozen Keith "Apache" Sheppards. Selling the Sox was the best thing that ever happened to the team because it did get them Manny. And Damon. And extensions for Pedro and Nomar. There was a real change in the SOP of the Sox front office in the late 90s. And that was good.
 

simplicio

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They really got lucky that they were able to stash Rusney like they did and write it off as just a cash loss; if he'd actually had an effect on the cap I think he'd be in the conversation here. But for me it has to be Panda, as the most obvious bad move from day 1 that somehow looked even worse with every day that followed.
 

BaseballJones

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Sandoval in the three years before coming to Boston:

1,509 ab, 179 r, 78 2b, 42 hr, 215 rbi, .280/.335/.424/.759, 116 ops+

His worst of the three years he put up a 111 ops+.

With Boston he put up a 71 ops+ in 161 games. Then the two years after being in Boston, he did this for SF:

502 ab, 33 2b, .259/.311/.466/.778, 108 ops+

So basically he was a good hitter before Boston got him, an epic catastrophe with Boston, and then pretty good again the two years after leaving Boston.

So bizarre.
 

cornwalls@6

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They really got lucky that they were able to stash Rusney like they did and write it off as just a cash loss; if he'd actually had an effect on the cap I think he'd be in the conversation here. But for me it has to be Panda, as the most obvious bad move from day 1 that somehow looked even worse with every day that followed.
Agree, that would be my pick as well. It's the one signing of this era that felt like it was almost completely driven by the marketing department. Coming off a disastrous season, fan interest waning badly, let's sign the fat, cute, dude who had a good World Series, and make a folk hero out of him. Never mind the screaming red flags about his conditioning, and where it was likely to go in the near future, and how this fan base would react to a woefully out of shape player the first time he struggled. I'm not sure if I was completely down on it when they announced, but by the first time we saw him in spring training, I remember thinking this an impending disaster.
 

Petagine in a Bottle

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True but Pablo’s OPS by year before he made to to Boston went from 909 to 789 to 758 to 739. What’s odd is that he had two solid years with the Giants after the Sox dumped him. But given his body type and horrible plate discipline, I don’t think anyone should have been surprised by his rapid and early decline.
 

snowmanny

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Don't sleep on, or with, Rusney Castillo. The Sox signed him in August, 2014 for $72.5 mm.

Castillo put up good numbers, albeit in short seasons, in Cuba in 2010-11and 2011-12. He then saw his numbers decline -- his batting average was .274 for example -- in 2012-13 and he missed almost all of 2013-2014 until the Sox signed him due to injury.

So off a few strong seasons in Cuba, which is effectively a AAA comp, and a down year and a year in which he didn't play, the Red Sox gave him an enormous contract.

Trying to catch the Cuban wave or some such thing.

We all saw the results and his inability to stick with the team.

At least guys like Sandoval and Crawford had enjoyed some success in the majors and at least whatever success they did enjoy wasn't so limited.

His numbers:

https://www.baseball-reference.com/register/player.fcgi?id=castil000rus
It’s the getting distracted by the World Series and somehow not winning the bidding on Abreu, the obvious fit for the next year’s team with Napoli a FA....and then within the year giving big bucks to Rusney, and taking on the at-the-time-thought-to-be-only-maybe-permanently-disabled Craig as mid-season additions to a last place club that makes all this such a cluster. Just a weird weird sequence of events.
 

bigq

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It was strange, for a team that made a big splash in the first free agent winter (Bill Campbell), it didn't seem like the Red Sox really understood free agency until the signed Manny.
I agree with your point however don’t forget that Jerry Remy was signed as a free agent in 1981. ;)
 

Whoop-La White

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And, to be fair, when Lou Gorman was hired on, he did focus on rebuilding a barren farm system, which bore fruit in 1986 and helped them further in the latter part of the 80's. Thanks to collusion among the MLB owners (Sox included), there was very little player movement during the mid-1980's. And there was always some drama; they lost Bruce Hurst to free agency because they toed the league line on the lockout language, a trend which hurt them throughout the early 90's as well. It was part of the reason why Gorman had to overpay for the 2nd tier free agents like Danny Darwin or Matt Young or Otis Nixon or Andre Dawson. Boston just wasn't a destination for the premier players, and a lot of players, especially Black players, routinely would place Boston on their no-trade lists.
By coincidence a few weeks ago I stumbled on this old article from the Dawson signing in which Gorman says "We actually hadn't thought about Dawson. We wanted to sign (free agent Mark) McGwire but we couldn't work out the dollars."'

I remembered feeling that Dawson was a broken, lackluster runner-up prize after other players who could have been difference makers. The year before the Sox were supposedly in on Bob Welch following his Cy Young year and ended up with Young and Darwin. And you're right, there was always some narrative about good players never wanting to play in Boston, whether due to cramped clubhouses or ownership or cold weather or racism.
 

Van Everyman

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The Castillo deal is and forever will be hilarious. They gave him a ton and yet it was worth more to them to pay him that much to stick in AAA, because it would have hurt the team far more to have him on the MLB roster. I don't think I've ever seen anything like that in sports before.
It's funny in part because we have heard forever about the Sox want to be small market smart with big market resources. And yet, they have had a lot of deals (as mentioned in this thread) completely blow up on them. Theo, for all his legend, had Renteria, Lugo, Clement, and Crawford (I liked Wells, actually). Cherington had Hanley and Panda. Dombrowski the Sale extension. There are others of course -- but they've always seemed to recover from deals that would've otherwise crushed other franchises for years.

Bloom is the only GM thus far not to have a whopper mistake. Until Story breaks his ribs putting on his cowboy boots, that is.
 

lexrageorge

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Like I said, it seems to me Gorman lost his fastball and was just throwing money at names because that's what sells tickets in the winter. While the Duke was the prototype for the dumpster diving GMs, who loved finding value in other teams' throwaways. And I think that works to an extent. For every Troy O'Leary there's two Midre Cummings. For every Tim Wakefield, there's a dozen Keith "Apache" Sheppards. Selling the Sox was the best thing that ever happened to the team because it did get them Manny. And Damon. And extensions for Pedro and Nomar. There was a real change in the SOP of the Sox front office in the late 90s. And that was good.
Manny was signed when JRY Trust still owned the Sox. As was Damon.
 

chrisfont9

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I don't think you guys are missing too many possibilities. For me, the most disappointing one would be Edgar Renteria, just because it seemed like a sure bet. But in general my takeaway here is that the Sox have done a decent job of not hamstringing themselves with horrible contracts. The worst one here wouldn't make the top 5 of the Mets, Yankees, Angels and probably a few other clubs.
 

Van Everyman

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Re. Renteria seeming like a sure bet, he was one of the first guys that made me start to think that some guys are cut out for Boston and others aren't. Renteria started making excuses (snakes in the grass anyone?) for why he was playing so poorly -- and the Sox clearly cut bait on him quickly, which suggests that they didn't think it was going to get much better in Boston. Meanwhile, you may not have liked the David Wells contract or how it turned out, but he seemed to be totally comfortable playing in Boston on the big stage.

Crawford clearly wasn't. One of the crazier aspects of the Crawford deal (and it's worth re-reading some of the threads on him) is that somehow he signed a 7-year deal without doing any research as to what it was like to play here. Meanwhile, Theo had a PI (or maybe it was Allard Baird?) tail him for months and he didn't turn up any red flags either. And yet, everyone thought it was worth diving into a $142M deal.

Another guy who struggled with Boston was Coco Crisp, who by all accounts went from being a positive energy guy to being super surly after he broke his finger at the beginning of the 2006 season and never really came out of it. Seth Mnookin wrote about his attitude problems, IIRC. Like Renteria, he went on to have a decent career, post-Boston.

Which is another way saying, it's as interesting to wonder why some of these contracts were so bad as it is to identify which ones are the worst.
 

John Marzano Olympic Hero

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Manny was signed when JRY Trust still owned the Sox. As was Damon.
Yes, I know thist. But I should have been more clear. From what I've read, DD was told to sign some big ticket free agents because the team was getting ready to be sold and Harrington wanted a championship for the Yawkey trust. Thus the sale (or threat of a sale) motivated the team to spend.

Re. Renteria seeming like a sure bet, he was one of the first guys that made me start to think that some guys are cut out for Boston and others aren't. Renteria started making excuses (snakes in the grass anyone?) for why he was playing so poorly -- and the Sox clearly cut bait on him quickly, which suggests that they didn't think it was going to get much better in Boston. Meanwhile, you may not have liked the David Wells contract or how it turned out, but he seemed to be totally comfortable playing in Boston on the big stage.
I remember that the temperature on this board was very cool to Renteria. Bill Simmons (when he still posted here) loved it because he claimed that Renteria was the only one that scared him on the 2004 Cards (I think he did, it's been almost 20 years) which got a lot of laughs from people here. Simmons scrammed after that.

But most people wanted the Sox to keep Cabrera. But that wasn't going to happen.
 

moondog80

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Wasn’t Cabrera rumored to be getting very friendly with some teammate’s wife/gf?
 

Red(s)HawksFan

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Re. Renteria seeming like a sure bet, he was one of the first guys that made me start to think that some guys are cut out for Boston and others aren't. Renteria started making excuses (snakes in the grass anyone?) for why he was playing so poorly -- and the Sox clearly cut bait on him quickly, which suggests that they didn't think it was going to get much better in Boston. Meanwhile, you may not have liked the David Wells contract or how it turned out, but he seemed to be totally comfortable playing in Boston on the big stage.
I thought snakes in the grass was a Beltre expression? And to be fair, the field conditions were shitty for decades until they did a complete overhaul about a decade ago.

IIRC, Renteria hurt his back early in that season (maybe during spring training?) and played through it which affected him in the field and at the plate. If he ever got healthy that year, it didn't matter because the media and fans had written him off. I always thought he would not have been traded if Theo hadn't quit that winter, and maybe the turnaround he had in Atlanta (8.3 bWAR the next two years) happens here. I just don't see Theo trading both Renteria and Hanley in the matter of a week and leaving the team with no viable SS options and no tangible plan to replace them. I mean, Alex Gonzalez could not possibly have been the plan going into that off-season.
 

Smiling Joe Hesketh

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I remember that the temperature on this board was very cool to Renteria. Bill Simmons (when he still posted here) loved it because he claimed that Renteria was the only one that scared him on the 2004 Cards (I think he did, it's been almost 20 years) which got a lot of laughs from people here. Simmons scrammed after that.

But most people wanted the Sox to keep Cabrera. But that wasn't going to happen.
No, Simmons claimed, after Renteria was traded after the 2005 season, that he hated the Renteria signing because Renteria was a guy who never scared him in the 2004 World Series. When it was pointed out that his feelings about being scared don't matter and in fact Renteria had batted 333/412/533 in the 2004 World Series and was in fact one of the few guys for St. Louis who actually showed up, he doubled down, got defensive, and ran away.
 

Petagine in a Bottle

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Renteria hit 287/327/401 for the Cards in 04, and then 276/335/385 for the Sox. I guess the expectation was we’d be getting the 03 Edgar (330/394/480) but that year, and 2007 really stand out as outliers. His career numbers are pretty similar to what the Sox got in his age 28 year.
 

Smiling Joe Hesketh

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Renteria hit 287/327/401 for the Cards in 04, and then 276/335/385 for the Sox. I guess the expectation was we’d be getting the 03 Edgar (330/394/480) but that year, and 2007 really stand out as outliers. His career numbers are pretty similar to what the Sox got in his age 28 year.
The back injury really limited him in the field.

He's widely seen as an awful player but he did play until the 2011 season so he was hardly washed up when the Sox dumped him. He was a full time starter for 4 more years and then played about 1/2 time for two more after that, got himself a ring in 2010 with SF.
 

John Marzano Olympic Hero

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No, Simmons claimed, after Renteria was traded after the 2005 season, that he hated the Renteria signing because Renteria was a guy who never scared him in the 2004 World Series. When it was pointed out that his feelings about being scared don't matter and in fact Renteria had batted 333/412/533 in the 2004 World Series and was in fact one of the few guys for St. Louis who actually showed up, he doubled down, got defensive, and ran away.
Oh yeah, you're 100% right. If only I could remember the mean poster that scared off Simmons. Who was that again?
 

BuellMiller

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The Manny signing was huge, but should also point out that he was their 2nd choice after they heavily pursued Mike Mussina and lost out to the Yankees.
There are some interesting alternate histories that could have happened here...what if Mussina signs with the Red Sox instead. Do the Yankees shift to Manny, or maybe another pitcher (saving Mike Hampton from Colorado? or saving Colorado from Mike Hampton). Maybe they go after A-Rod a few years early (maybe the whole alternate history is triggered because Brosius blows out his knee playing basketball three years before AFB would). If Manny goes back to Cleveland, do the Red Sox bring Ellis Burks back a few years earlier (although, it looks like Burks signed a bit earlier in the offseason than Mussina, and maybe Cleveland signed JuanGon as a replacement after Manny signed with the Red Sox IRL).
In 2001, have to assume the Red Sox still end up far out of the playoffs with Nomar and Pedro missing most of the season, and Jimy still gets canned during the season and DD after it. But 2002 would feature a pretty good big 3 in the rotation with Pedro, Lowe, and Mussina. Depending on who they got to replace LF/DH, maybe the improvement of Mussina over Burkett/Frank Castillo gets them into the playoffs and Grady Little can again bungle it and get fired a year early. One could only hope...
 

Manuel Aristides

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B. I figured in 2004 he'd come back to haunt us when he played for the Yankees -- and he went down meekly in the ALCS, even though Foulke was gassed and getting by on smoke and mirrors.

...

I think it is Rusney Castillo...he was so overpaid the team literally could not afford to play him. He defined negative value. At least Crawford was worth trading.
I remember hearing an anecdote that, when Clark was up in the 9th in '04 G6, where he could have walked it off with a homer, that Theo Epstein was doing the fan thing of "not this guy, not this fucking guy, it can't be this guy". Just locked in how much I love Theo.

As for Rusney, truly terrible contract, but, I don't think it can be worst ever since they effectively got it off the books by forcing him to play it all at AAA. A billionaire losing money on an investment is no skin off my nose so long as the investment isn't counting towards the salary cap of my preferred team.
 

jose melendez

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It certainly can, but I was being diplomatic.



Like I said, it seems to me Gorman lost his fastball and was just throwing money at names because that's what sells tickets in the winter. While the Duke was the prototype for the dumpster diving GMs, who loved finding value in other teams' throwaways. And I think that works to an extent. For every Troy O'Leary there's two Midre Cummings. For every Tim Wakefield, there's a dozen Keith "Apache" Sheppards. Selling the Sox was the best thing that ever happened to the team because it did get them Manny. And Damon. And extensions for Pedro and Nomar. There was a real change in the SOP of the Sox front office in the late 90s. And that was good.
Midre Cumming had an OPS+ of 120 in his first stint with Boston. He wasn't Troy O'leary, but he was a productive pinch hitter for a year.

Edit: Fun fact Yummy's best OPS+ was 116.
 

jose melendez

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Yes, I know thist. But I should have been more clear. From what I've read, DD was told to sign some big ticket free agents because the team was getting ready to be sold and Harrington wanted a championship for the Yawkey trust. Thus the sale (or threat of a sale) motivated the team to spend.



I remember that the temperature on this board was very cool to Renteria. Bill Simmons (when he still posted here) loved it because he claimed that Renteria was the only one that scared him on the 2004 Cards (I think he did, it's been almost 20 years) which got a lot of laughs from people here. Simmons scrammed after that.

But most people wanted the Sox to keep Cabrera. But that wasn't going to happen.
Cabrera also hit worse than injured Renteria in 2005, though he was a very good defender and ER was awful.
 

BaseballJones

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There are some awful contracts that you end up surprised they were so awful, and other awful contracts that you had a pretty good feeling right away were going to be awful (or at least not wise).

To me, Carl Crawford fits in the former category, and I think the Chris Sale extension probably fits in the latter category.