Hold 'em or fold 'em - A Mookie free zone.

grimshaw

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What are some of the most significant non-moves this franchise has done with their own free agents over the years?

Letting Pedro and Ellsbury go seem to be the biggest winners. Thanking Jason Bay with a gift basket for his services also worked out well, and he was a big fan favorite.

I'm having a tough time coming up with ones they'd want a redo on during the Henry era, but Fisk is the obvious one outside that. Maybe Beltre, but I'm not sure he was signable.
 

nayrbrey

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DLowe was one who I hoped they would have kept, if just to not have to have signed either Clement or Wells for 05. Although it looks like They signed for 3 year deals while Lowe got a 4 year one at higher AAV.

Edit: Wells was 2/18, Clement 3/25.5 while Lowe got 4/36 from Dodgers. So all about the same AAV, just different length.
 
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nattysez

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This thread raises one of the great unknowable Sox questions: would Clemens been as motivated/gotten on the juice if the Sox had signed him to a long-term deal rather than letting him ride off to Toronto into the "twilight of his career?"
 

grimshaw

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This thread raises one of the great unknowable Sox questions: would Clemens been as motivated/gotten on the juice if the Sox had signed him to a long-term deal rather than letting him ride off to Toronto into the "twilight of his career?"
I think wheezing the juice was inevitable for him at any point, though all time greats live for the haters.
 

Leather

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Despite my sadness at the time, it was for the best that they did not sign Nick Esasky to a long-term deal.
 

Time to Mo Vaughn

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Letting Mo Vaughn go broke my 12 year old heart, but it certainly was correct in hindsight. Hard to say what would have happened to Vaughn's career though without breaking his ankle in his first play for the Angels.
 

RIFan

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A very underrated loss was Bruce Hurst. Hurst didn't even want to go to free agency after coming off his best season, but good old Lou Gorman wanted to play hardball and let him test the market. Sox finished 1st in the division in 88 with upcoming stars like Burks and Greenwell. They finished in 3rd, 6 games behind Toronto, in 89. Hurst went 15-11 with a 131 ERA+ with San Diego. The Sox trotted out the likes of Wes Gardner, Mike Smithson, and Eric Hetzel for 46 starts. All were below league average. If they re-signed Hurst it's more than possible that they three peat as division champs. It also would have set them up better in 1990 when you would have had a 1-3 rotation of Clemens, Hurst, and Boddicker. Taken it to the most unfavorable possible place, maybe they get to keep Greg Harris in the bullpen that year and don't feel the need to add another reliever and trade a certain prospect first baseman.
 

jaytftwofive

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A very underrated loss was Bruce Hurst. Hurst didn't even want to go to free agency after coming off his best season, but good old Lou Gorman wanted to play hardball and let him test the market. Sox finished 1st in the division in 88 with upcoming stars like Burks and Greenwell. They finished in 3rd, 6 games behind Toronto, in 89. Hurst went 15-11 with a 131 ERA+ with San Diego. The Sox trotted out the likes of Wes Gardner, Mike Smithson, and Eric Hetzel for 46 starts. All were below league average. If they re-signed Hurst it's more than possible that they three peat as division champs. It also would have set them up better in 1990 when you would have had a 1-3 rotation of Clemens, Hurst, and Boddicker. Taken it to the most unfavorable possible place, maybe they get to keep Greg Harris in the bullpen that year and don't feel the need to add another reliever and trade a certain prospect first baseman.
Wasn't 89 basically Hursts last good year. I didn't check stats but I thought he went downhill after that. Could be wrong.
 

RIFan

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Wasn't 89 basically Hursts last good year. I didn't check stats but I thought he went downhill after that. Could be wrong.
Nope. ERA+ in SD 131, 122, 116, 93. WAR 6.5, 5.0, 2.9, 1.0 He only signed a 3 year deal so the fall off happened after that deal. His shoulder surgery happened in 1992 which led to him going down hill.
 

TFisNEXT

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Wasn't 89 basically Hursts last good year. I didn't check stats but I thought he went downhill after that. Could be wrong.
No, he was good in 1990 and 1991 too. ERA+ of 122 in 1990 and 116 in 1991 while pitching over 220 innings each year.

edit: RIF beat me to it
 

jaytftwofive

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I think Boggs is on the list. I forget the details of his departure, other than him having an off year, but he had some pretty good years after he left the Sox.
An there was also the story or urban legend that at one point in 91, or 91 off season, that the Yanks were possibly offering Bernie Williams and Pettitte for Boggs. Of course that would have been highway robbery but the story is Gene Michael backed off when it came close.
 

brs3

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Andrew Benintendi, though perhaps he needed a fresh start.
Andrew Miller. I know they don't get E-Rod without Miller, but what a force he was.
Derek Lowe. In my brain I know his NL success wouldn't have translated to AL success, but he sure looked good after he left.
 

Hank Scorpio

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In hindsight, we should have kept Adrian Beltre for third, and let Youk hang on to first until Rizzo was ready.

This would have spared us Pablo Sandoval, and segued nicely into the Devers era. We could have sold high on Wombat, and could have traded Casey Kelly for something else.

How did Josh Reddick leave? I can’t recall, but if we held on to him, maybe we would have avoided the Carl Crawford fiasco.
 

jaytftwofive

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In hindsight, we should have kept Adrian Beltre for third, and let Youk hang on to first until Rizzo was ready.

This would have spared us Pablo Sandoval, and segued nicely into the Devers era. We could have sold high on Wombat, and could have traded Casey Kelly for something else.

How did Josh Reddick leave? I can’t recall, but if we held on to him, maybe we would have avoided the Carl Crawford fiasco.
Yes losing Beltre and Rizzo to me maybe no.2 next to Fisk. Mainly because A-Gon and Crawford were gone after a little over a year and a half, in the famous Nick Punto Trade. So we lost not 2 but 4 players who could have played. And how Beltre and Rizzo's careers got better and better.
 
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Red(s)HawksFan

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In hindsight, we should have kept Adrian Beltre for third, and let Youk hang on to first until Rizzo was ready.

This would have spared us Pablo Sandoval, and segued nicely into the Devers era. We could have sold high on Wombat, and could have traded Casey Kelly for something else.

How did Josh Reddick leave? I can’t recall, but if we held on to him, maybe we would have avoided the Carl Crawford fiasco.
Reddick was traded for Andrew Bailey. Incidentally, it followed the Crawford deal by a year. Arguably was facilitated by Crawford's presence.
 

Sandy Leon Trotsky

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In hindsight, we should have kept Adrian Beltre for third, and let Youk hang on to first until Rizzo was ready.

This would have spared us Pablo Sandoval, and segued nicely into the Devers era. We could have sold high on Wombat, and could have traded Casey Kelly for something else.

How did Josh Reddick leave? I can’t recall, but if we held on to him, maybe we would have avoided the Carl Crawford fiasco.
Yeah... this whole era was some bad Theo moves. He had blind spots (everyone does)... but they seemed obvious to me. He chose to stick with Anderson over Rizzo. Ryan Kalish over Josh Reddick. Was committed to getting Crawford, Adrian Gonzalez and was willing to push Youk back to 3rd when it was obvious he had passed that point.

There's some disagreement about the Rizzo/Anderson mess but it was pretty obvious by the time they were both in Portland which of Rizzo or Anderson should have been the keeper. But Anderson had the pedigree.
 

lexrageorge

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This thread raises one of the great unknowable Sox questions: would Clemens been as motivated/gotten on the juice if the Sox had signed him to a long-term deal rather than letting him ride off to Toronto into the "twilight of his career?"
Clemens was teammates with Conseco for 2 seasons, so my guess is that the juicing started while he was still with the Sox.

Only one poster seemed to keep bring up the Ellsbury non-signing years after it happened. It looked bad at the time, but it was a bullet dodged in the long run.
 

TFisNEXT

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All of the AGon/Crawford scenarios are interesting, but it should be noted that there's an excellent chance 2013 doesn't happen if they go another route.
 

Red(s)HawksFan

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I disagree on Ellsbury. We had Mookie ready.
Mookie was a single-A 2B when Ellsbury was allowed to walk as a free agent. If you want to argue they were okay with letting him go for reasons other than his contract demands were beyond what was reasonable, then the reason was JBJ despite his meager showing in 2013 when he was rushed up after a decent spring training and they had a roster spot because Ortiz started the year on the DL.
 

wiffleballhero

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In the simulacrum
Letting Mo Vaughn go broke my 12 year old heart, but it certainly was correct in hindsight. Hard to say what would have happened to Vaughn's career though without breaking his ankle in his first play for the Angels.
Vaughn would have also been better off continuing to hit in Fenway, independent of the ankle too. He was a sort of perfect Fenway lefty power hitter -- able to pull the ball deep but also able to exploit 'warning track power' the opposite way for doubles.
 

RSN Diaspora

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A very underrated loss was Bruce Hurst. Hurst didn't even want to go to free agency after coming off his best season
I don't recall it that way at all. I know that's how he frames it in the link you provided, but I distinctly recall him wanting to be closer to Utah and in an environment more in line with his Mormon values than the Sox clubhouse (lots of booze, the infamous "Can's Film Festival", etc.).
 

chrisfont9

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Johnny Damon departure hurt a bit, basically ruined 2006 (along with Beckett's off year and Matt Clement being Matt Clement). Yes, by the end of 2007 we had a solution to the problem, but for the better part of two seasons it was bad, and Damon was very good for most of the next six years. It should definitely be in the top ten of bad non-trade departures.
 

TFisNEXT

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Kind of a weird one, but I distinctly remember feeling like the ‘09 - ‘11 teams really could have used Coco Crisp as outfield depth.
Probably not possible without trading Ellsbury, but you are correct in the sense that Jacoby was injured in 2010 so we were using a cooked Mike Cameron, Daniel Nava, and Darnell McDonald. Jacoby basically missed all of 2010. Pedroia's injury was a killer too that year. Otherwise that team might have made the playoffs. Kind of hard to believe that team won 89 games with all the injuries they had.
 

chrisfont9

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I don't recall it that way at all. I know that's how he frames it in the link you provided, but I distinctly recall him wanting to be closer to Utah and in an environment more in line with his Mormon values than the Sox clubhouse (lots of booze, the infamous "Can's Film Festival", etc.).
I remember him saying that. Who knows what these guys really think vs what they are told to say? Here he is years later telling the Globe he wished he hadn't left. Even that sounds a bit like telling Boston fans what they want to hear.
https://www.bostonglobe.com/sports/2015/12/01/catching-with-bruce-hurst-series-mvp-who-wasn/Vp5tPmoGkE9MDBCG3fNHZJ/story.html

He sounds like a guy who was really connected to the organization and probably would have signed to stay on if Gorman had any ability to connect with players, which good lord. Just a guess that Hurst on a fat contract would have been fine with flying back to Utah and his people in the offseason.
 

scottyno

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Beltre, though I think literally 0 people in the world would have predicted how good his age 32-38 seasons would have been after he left Boston so it's a little hard to knock them on that.
 

grimshaw

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Beltre, though I think literally 0 people in the world would have predicted how good his age 32-38 seasons would have been after he left Boston so it's a little hard to knock them on that.
I don't recall a ton of push back when he signed that deal though it was fairly modest AAV at 5/$80. The Rangers then re-signed him.

The weird thing is, the Sox moved an aging Youkilis back to third and were not shy about throwing around long term contracts with Crawford, Lackey and Adrian Gonzalez all who would be past prime on the back end. MIddlebrooks was a big whiff.

Slight rehash from above but in retrospect, this was one that really came back to bite them. They had serious chemistry issues and could have used him. IIRC this is also back when Theo didn't really want to splurge on flashy guys just to keep up ratings and felt he was being overruled. Maybe he did want him back.
 
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Red(s)HawksFan

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Dwight Evans.

1) There was no need to watch him play his final year for the Orioles.
2) And maybe we wouldn't have signed Jack Clark.
From a sentimentality standpoint, I can't argue with this.

From an on-the-field production standpoint, Clark was the right choice. (2.3 WAR vs 0.6 WAR for Dewey in Baltimore)
 

chawson

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What is this, like our sixth ‘Let’s Remember Some Guys’ nostalgia thread this year? I’ll say Carlos Peña.
 

lexrageorge

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I remember him saying that. Who knows what these guys really think vs what they are told to say? Here he is years later telling the Globe he wished he hadn't left. Even that sounds a bit like telling Boston fans what they want to hear.
https://www.bostonglobe.com/sports/2015/12/01/catching-with-bruce-hurst-series-mvp-who-wasn/Vp5tPmoGkE9MDBCG3fNHZJ/story.html

He sounds like a guy who was really connected to the organization and probably would have signed to stay on if Gorman had any ability to connect with players, which good lord. Just a guess that Hurst on a fat contract would have been fine with flying back to Utah and his people in the offseason.
One of the big issues for Hurst was the Red Sox insistence on using the least favorable lockout language in their agreements, as an extended lockout was expected in 1990 due to the collusion fiasco. There was a lockout that cancelled most of spring training in 1990, but it was resolved in time to allow for a slightly delayed start to the regular season.

Apparently the Sox were holding the hardest line among all MLB teams in terms of language that would basically mean the player does not get paid in the event of a lockout with no CBA in place.
 

Marciano490

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A very underrated loss was Bruce Hurst. Hurst didn't even want to go to free agency after coming off his best season, but good old Lou Gorman wanted to play hardball and let him test the market. Sox finished 1st in the division in 88 with upcoming stars like Burks and Greenwell. They finished in 3rd, 6 games behind Toronto, in 89. Hurst went 15-11 with a 131 ERA+ with San Diego. The Sox trotted out the likes of Wes Gardner, Mike Smithson, and Eric Hetzel for 46 starts. All were below league average. If they re-signed Hurst it's more than possible that they three peat as division champs. It also would have set them up better in 1990 when you would have had a 1-3 rotation of Clemens, Hurst, and Boddicker. Taken it to the most unfavorable possible place, maybe they get to keep Greg Harris in the bullpen that year and don't feel the need to add another reliever and trade a certain prospect first baseman.
Is he the guy who said he felt like he worked for UPS pitching in the Padres uniform?
 

Van Everyman

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The 2010-11 offseason, Beltre was on the market seemingly for forever, despite having put up great numbers on a “prove it” one year $8M deal with the Sox..Even at the time, it seemed like that deal for Adrian Gonzalez was somewhat unnecessary. Youk was in his prime, an exceptional fielder by that point and a perennial MVP vote getter. As noted, the problem with 2010 was other guys got injured.

As an aside, I’ve always been salty that Theo barfed Rizzo up in the Gonzalez deal and then found a way to get him back from the Padres just a few years later with the Cubs and Hoyer where he turned into a stud. I know there was nothing officially shady but it seemed kind of wrong.
 

ngruz25

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What made the lackluster effort to re-sign Lester really hurt was when the Sox backed up the Brinks truck to land David Price one season later. We all knew of the organization's philosophy on signing pitchers over 30 to long-term deals, so letting Lester go made some sense. And then it didn't.

Of course, 2018 healed a lot of wounds.