Let's Talk Exten$ions...

TomBrunansky23

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Man, that's the hill you want to die on?

As in, wouldn't it be great if Ellsbury were sucking up $21.9M of Mr. Henry's dead AAV money instead of the Steinbrenners'?
I'm simply pointing out the lengthy and consistent history of this team's top tier free agents reaching the open market and walking. My belief is that Betts will be next on that list. Your choices are ride it out or trade him before he leaves.
 

TomBrunansky23

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But Jon Lester was on your list. That means it is not history.
You're correct insofar as it wasn't a perfectly analagous situation due to the trade, but you have to acknowledge that many thought he'd turn right back around and sign here once free agency opened. Didn't happen.

I guess I'd ask for an opposite example - when has a top tier guy ever hit the open market and then opted to re-sign here? There must be an example but I just can't think of one. I feel like we will have to debate what "top tier" means before we find someone who fits.
 

azsoxpatsfan

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You're correct insofar as it wasn't a perfectly analagous situation due to the trade, but you have to acknowledge that many thought he'd turn right back around and sign here once free agency opened. Didn't happen.

I guess I'd ask for an opposite example - when has a top tier guy ever hit the open market and then opted to re-sign here? There must be an example but I just can't think of one. I feel like we will have to debate what "top tier" means before we find someone who fits.
Ortiz in 2012. And your “lengthy and consistent history” is five guys over 25 years, two of which combined for three all star games. And for the sake of argument let’s say you’re right and he really doesn’t want to be here. What the fuck is he supposed to say when asked? You’re annoyed that he said he likes it here and has enjoyed it and that reports that he wants to leave are false. Would you rather he say yea I hate it and I’m leaving as soon as I can?
 

TomBrunansky23

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Ortiz in 2012. And your “lengthy and consistent history” is five guys over 25 years, two of which combined for three all star games. And for the sake of argument let’s say you’re right and he really doesn’t want to be here. What the fuck is he supposed to say when asked? You’re annoyed that he said he likes it here and has enjoyed it and that reports that he wants to leave are false. Would you rather he say yea I hate it and I’m leaving as soon as I can?
Are you talking about Ortiz signing in February of 2012? Because he was still arb-eligible at the time.

https://www.espn.com/mlb/story/_/id/7570133/david-ortiz-boston-red-sox-agree-deal-arbitration
Or are you talking the November 2012 two year deal signed a few hours into free agency for a 37 year old?

https://www.usatoday.com/story/sports/mlb/2012/11/02/red-sox-david-ortiz-two-year-contract-26-million/1678345/
Yes, I suppose Ortiz technically did get to free agency and re-signed. Hardly the same thing as free agency for a 28 year old (as Mookie will be on 10/7/20) in his prime.
 

azsoxpatsfan

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Are you talking about Ortiz signing in February of 2012? Because he was still arb-eligible at the time.

https://www.espn.com/mlb/story/_/id/7570133/david-ortiz-boston-red-sox-agree-deal-arbitration
Or are you talking the November 2012 two year deal signed a few hours into free agency for a 37 year old?

https://www.usatoday.com/story/sports/mlb/2012/11/02/red-sox-david-ortiz-two-year-contract-26-million/1678345/
Yes, I suppose Ortiz technically did get to free agency and re-signed. Hardly the same thing as free agency for a 28 year old (as Mookie will be on 10/7/20) in his prime.
The one signed a few hours into free agency. Obviously not the same thing but there aren’t a ton (if any) players in Sox history as good and young as mookie who hit free agency. One of your examples was a 32 year old 2 time all star Johnny Damon who to that point in his career was a .290 hitter who averaged 12 home runs per season. There just aren’t many accurate comparisons. But again, what would you have preferred he say? Because I think what he said was basically perfect. He has no obligation to resign with us, and who knows what he’s going to do, but he’s not saying anything worth getting upset about.
 

Bigpupp

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Ortiz wasn't "arb-eligible" in 2012. At least not like we usually use that phrase. It only takes 6 years of service time to be a free agent and he had well over that in 2012. Ortiz reached free agency, then accepted what we now call the qualifying offer, which at the time required a trip to arbitration to figure out his salary for the next year.

As for Mookie...sure he might sign somewhere else. But I'd rather keep him for the next year and half and have a great shot at signing him, than repeat the same mistake we made with Lester.
 

lexrageorge

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You're correct insofar as it wasn't a perfectly analagous situation due to the trade, but you have to acknowledge that many thought he'd turn right back around and sign here once free agency opened. Didn't happen.

I guess I'd ask for an opposite example - when has a top tier guy ever hit the open market and then opted to re-sign here? There must be an example but I just can't think of one. I feel like we will have to debate what "top tier" means before we find someone who fits.
You will not find a lot of examples because the Sox have tended to extend their young players before they hit free agency (Pedroia, Youkilis, and now Xander). Or they were OK with their departures (Ellsbury, Damon, Kimbrel, Papelbon, Jason Bay, and even Pedro). Or they were traded (Nomar, Lester, Andrew Miller, Nick Punto). The Sox probably should have resigned Beltre, and probably could have had they been more aggressive, but it was clear the Sox were OK with him leaving as well. The Lester situation was poorly handled, as there was still some lingering resentment from the absurd 5/70 offer the prior offseason. But the Sox have significantly revamped their front office since then. This is a very different front office from 2014.

Varitek and Lowell resigned here. They weren't what I would call "top tier", but Varitek was highly regarded among catchers, and Lowell had just won World Series MVP.

There is obviously risk in letting a player get to free agency, and that risk is greater if the player was willing to sign an extension earlier. Greener pastures are a thing, and often times free agents across MLB have noted that their prior team had a chance to sign them the season before but decided not to. So far, Betts hasn't even entertained an extension. But that could change this offseason.
 

Red(s)HawksFan

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Here's the flaw in this discussion. Saying the Sox "let" top-tier players get to free agency assumes that it's one-sided. They can want to re-sign the player all they want, but if the player is bound and determined to hit free agency, what can they do? It's his right and he can elect to do what he wants no matter how hard the team tries (or doesn't try) to sign him long term. Let's not take away the player's agency in this in a quest to paint the team as bad operators.
 

Danny_Darwin

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I'm not sure how relevant examples of free-agency departures that happened on Larry Lucchino's watch are going forward. Kimbrel is the highest-profile departure of the Dombrowski era, but I'm not sure that comparison applies here, either - the Sox weren't the only team who didn't want to sign him, clearly.
 
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Pandarama

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Varitek and Lowell resigned here. They weren't what I would call "top tier", but Varitek was highly regarded among catchers, and Lowell had just won World Series MVP.
How quickly World Series MVP (and free agent) Steve Pearce seems to have been forgotten.
 

Savin Hillbilly

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The wrong side of the bridge....
There really are some people who a fine just making a ridiculous amount of money and don't feel the need to make the most money. Xander appears to be one of those people. Mookie appears not to be. That doesn't make Xander foolish and it doesn't make Mookie greedy. People are actually different.
The bolded bits feel like trying to have it both ways. "Needing to make the most money" is pretty much exactly what the word "greedy" means. But wanting to go to free agency does not necessarily indicate a "need to make the most money." It may just indicate a reluctance to foreclose options prematurely. How Mookie views those options, or prioritizes their benefits, we have no idea. Conversely, Xander may have had reasons for signing an extension that having nothing to do with not feeling the need to make the most money. We have no idea. The difference may boil down to Mookie being more of a gambler by nature, and/or Xander valuing stability more. We have no idea.
 

johnnywayback

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In the mess of deadline tweets yesterday I stumbled across this. Gammons caveats apply, but if true this winter might be centered around trading Mookie.

https://twitter.com/redsoxstats/status/1156593098291650560?s=21
It should be. Well, the second half, anyway. The first half should be centered around finding out if he's going to insist on going to free agency, or whether he's ready to sign the massive, bigger-than-everyone-but-Trout extension I'm sure we're going to offer. If not -- whether it's because he wants to go somewhere else, or because he wants to see what the market is like, or because he thinks he can have an extraordinary 2020 that boosts his value beyond Trout's -- then we have to trade him. Losing him for nothing destroys the franchise in 2021 and beyond. But if that becomes a real possibility, trading him for an elite prospect and using the money to sign Gerrit Cole makes 2020 a competitive year in the Sale-Bogaerts window and extends that window a bit into the years when Sale is on the downside, Bogaerts ages off SS, and Devers is the star of the team.
 

Red(s)HawksFan

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It should be. Well, the second half, anyway. The first half should be centered around finding out if he's going to insist on going to free agency, or whether he's ready to sign the massive, bigger-than-everyone-but-Trout extension I'm sure we're going to offer. If not -- whether it's because he wants to go somewhere else, or because he wants to see what the market is like, or because he thinks he can have an extraordinary 2020 that boosts his value beyond Trout's -- then we have to trade him. Losing him for nothing destroys the franchise in 2021 and beyond. But if that becomes a real possibility, trading him for an elite prospect and using the money to sign Gerrit Cole makes 2020 a competitive year in the Sale-Bogaerts window and extends that window a bit into the years when Sale is on the downside, Bogaerts ages off SS, and Devers is the star of the team.
The bolded is a bit of hyperbole, don't you think? First, they aren't going to lose him for nothing even if he walks after 2020. They'll get some sort of compensation if he signs elsewhere. Second, I'm having a hard time buying that 30 year old Gerritt Cole extends the "Sale-Bogaerts window" in 2021 and beyond any more capably than 28 year old Mookie Betts. There's very little reason why the Sox shouldn't be willing to spend top dollar to keep Mookie around, even if that means waiting until he hits the market and discovers exactly what other teams are willing to pay. Failing to extend him before he hits free agency doesn't equal losing him in free agency.
 

Harry Hooper

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There's one unassailable fact: if you trade Mookie this winter, you don't have him playing for you and winning games in 2020. I don't accept the "letting him go for nothing" concept. You get something, him contributing on the field next season.

You want to talk about the Sox letting someone go for nothing, think Carlton Fisk.
 

JBJ_HOF

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I don't see why this is so confusing

Keep him: you have him for 2020 and then he can walk for a fourth round draft pick if he chooses

Trade him: you get your return for him and you have $30 million to go after Castellanos, Ozuna, Cole, contract extensions, or wait for Springer, Correa, etc
 

bosockboy

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Option A is definitely extending him.

If he’s not open to it, then the equation of these two options gets interesting-

1) Playing out 2020 and risk losing him for a comp pick.
2) Trading him and having the return of the prospect package plus signing Cole, Castellanos and the flexibility to extend JBJ.
 

Red(s)HawksFan

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I don't see why this is so confusing

Keep him: you have him for 2020 and then he can walk for a fourth round draft pick if he chooses

Trade him: you get your return for him and you have $30 million to go after Castellanos, Ozuna, Cole, contract extensions, or wait for Springer, Correa, etc
What's the return for him if you trade him? If he's due $30M like you imply, I would imagine that shrinks the market considerably. There will be teams that simply can't afford him (or can't justify paying him for a year in which they likely won't contend anyway). There will be teams that can afford/justify his salary but don't have all that much to trade. And then there are teams who can afford him and have prospects to burn...a very short list I expect.

Trading a guy with a year left because you fear you can't/won't re-sign him is the move of a lesser market team years away from contending. None of that describes the Boston Red Sox. To me, talk of trading Mookie Betts this winter is insanity.
 

Danny_Darwin

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What's the return for him if you trade him? If he's due $30M like you imply, I would imagine that shrinks the market considerably. There will be teams that simply can't afford him (or can't justify paying him for a year in which they likely won't contend anyway). There will be teams that can afford/justify his salary but don't have all that much to trade. And then there are teams who can afford him and have prospects to burn...a very short list I expect.

Trading a guy with a year left because you fear you can't/won't re-sign him is the move of a lesser market team years away from contending. None of that describes the Boston Red Sox. To me, talk of trading Mookie Betts this winter is insanity.
Right. I have a feeling people need to re-calibrate expectations for a Mookie trade. I said this elsewhere, but the best comparison might be the Heyward trade a few years back. Granted, that couldn't have worked out better for the Braves, but I feel like most people here would be disappointed with the 2019 equivalent of 2014 Shelby Miller.

(Incidentally, by your criteria of "teams who can afford him" and "teams with the assets to make this work," my first thought as a trade partner was indeed the Braves.)
 

sean1562

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A lot depends on whether JDM opts out or not. At this point, I am kind of hoping he does so we can spend that money on pitching, be that someone like Cole for the rotation or some great relievers. With Devers breaking out and Xander sustaining his success from last season, offense is not this team's problem
 

johnnywayback

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The bolded is a bit of hyperbole, don't you think? First, they aren't going to lose him for nothing even if he walks after 2020. They'll get some sort of compensation if he signs elsewhere. Second, I'm having a hard time buying that 30 year old Gerritt Cole extends the "Sale-Bogaerts window" in 2021 and beyond any more capably than 28 year old Mookie Betts. There's very little reason why the Sox shouldn't be willing to spend top dollar to keep Mookie around, even if that means waiting until he hits the market and discovers exactly what other teams are willing to pay. Failing to extend him before he hits free agency doesn't equal losing him in free agency.
I mean, they'll get a fourth-round pick. That's a massive loss compared to what you could get in return for a year of Betts, even counting that year's worth of production.

As for Cole, he doesn't extend the window, it's the return for Betts that does. Imagine getting Drew Waters and one of the Braves' pitching prospects, and having another 3-WAR outfielder who doesn't even hit arb until at least 2023. That allows you to re-sign JBJ and not sweat Benintendi and Devers hitting arb while still having more room to add smaller pieces that we currently can't afford. What a Cole does is make up for the short-term loss of Betts in 2020 -- the point is that, if you have $30M to spend, you can replace a lot of Betts's value in the short term.