High-Class Problems: Worst Blunders of the Henry Era

Rough Carrigan

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I have my quibbles with them (mainly how Tito was treated), but otherwise this is correct. They’ve taken a franchise & have soared beyond all imagination. Kudos to them.
What are the three worst decisions present Sox ownership has made since they took control of the team? You might say the hirings of Grady Little and Bobby Valentine and the treatment they gave Tito on his way out. I was under the impression that all three were Lucchino operations.
 

TheoShmeo

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What are the three worst decisions present Sox ownership has made since they took control of the team? You might say the hirings of Grady Little and Bobby Valentine and the treatment they gave Tito on his way out. I was under the impression that all three were Lucchino operations.
I’m not sure from where you developed that impression.

Of the three, the only one that has been uniquely pinned on LL was Valentine.

Also, Henry has repeatedly said that organizational decisions are made collectively. The idea that Henry and Werner would not have significant input in any significant decision that involves this team seems very naive. As much as BV was very likely Larry’s guy, they all bought in to that hideous call.

Yes, these owners have been awesome. I frankly don’t think we need any caveats. Every organization makes mistakes. Expecting absolute perfection or saying “yeah but” every time we say they’re great is a little unfair. Think about how many winning calls they’ve made or been part of over the years. We should all have such a ratio of great to bad in our jobs and lives.

If you had told any of us after the Grady Boner that our team would go on to win 4 titles by November, 2018, we’d have all laughed pretty hard. The only constants during that period have been the owners, Sam Kennedy and some other lower level employees.
 

lexrageorge

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What are the three worst decisions present Sox ownership has made since they took control of the team? You might say the hirings of Grady Little and Bobby Valentine and the treatment they gave Tito on his way out. I was under the impression that all three were Lucchino operations.
I can give the ownership team a pass on Little. The team was already a couple of weeks into spring training when the sale went through, and retaining incumbent Joe Kerrigan was a non-starter for obvious reasons. The pool of candidates was thin; and Little had been bench coach of the team previously, so had some experience with the environment. Kind of felt bad for Mike Cubbage, though.
 
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I can give the ownership team a pass on Little. The team was already a couple of weeks into spring training when the sale went through, and retaining incumbent Joe Kerrigan was a non-starter for obvious reasons. The pool of candidates was thin; and Little had been bench coach of the team previously, so had some experience with the environment. Kind of felt bad for Mike Cubbage, though.
Agreed. I recall several articles from that period which stated that the players were thrilled when Grady was promoted to manager. Additionally, it's been frequently reported that Grady had been provided with ample analytics (which, among other things, documented Pedro's rapid loss of effectiveness beyond 100 pitches) and Grady willing ignored such information.

If anything, the rapid firings of Grady and Bobby V demonstrate how quickly this ownership group acts to rectify their mistakes.
 

m0ckduck

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What are the three worst decisions present Sox ownership has made since they took control of the team? You might say the hirings of Grady Little and Bobby Valentine and the treatment they gave Tito on his way out. I was under the impression that all three were Lucchino operations.
Great question.

- Treatment of Tito on way out, definitely
- 2011 is a murky period, but I would say Theo's departure was a significant organizational failure. I got the impression from pieces that I read at the time that he lost clout due to the fate of the 2009 and 2010 teams, which seems reactionary and short-sighted if true.
- There was a piece posted earlier this year about how the Sox had fallen behind other teams in terms of usage of advanced metrics. This seems to have entirely fallen by the roadside given the current atmosphere of group-Alex-hug-Cora, but at the time, it seemed like a woeful state of affairs
- Jon Lester contract negotiations? One can pin this on the Cherington regime, but it's the type of situation that strong ownership will often step in and mediate before things go off the rails entirely

I agree that that ownership deserves a pass on Little. As others have noted, there were no good options in spring 2002. Moreover, the clubhouse culture was so toxic and acrimonious after 2001 that I remember reading reports of players bursting into applause when Little was introduced and nodding in approval. Valentine was a bad hire, but after the 2011 debacle, I can't entirely blame them.
 

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What are the three worst decisions present Sox ownership has made since they took control of the team? You might say the hirings of Grady Little and Bobby Valentine and the treatment they gave Tito on his way out. I was under the impression that all three were Lucchino operations.
My vote would be Sandoval and Hanley Ramirez. That was so much money for so little output that covers the three worst decisions.
 

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What are the three worst decisions present Sox ownership has made since they took control of the team? You might say the hirings of Grady Little and Bobby Valentine and the treatment they gave Tito on his way out. I was under the impression that all three were Lucchino operations.
1. Pablo Sandoval. It was just idiotic, giving five years at big money to a guy who complained his previous team had the nerve to expect him to stay in reasonably good shape as he got into his 30s and never again had to worry about getting a big payday.

2. Treatment of Tito on his way out.

3. Lowball of Lester.
 

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1. Pablo Sandoval. It was just idiotic, giving five years at big money to a guy who complained his previous team had the nerve to expect him to stay in reasonably good shape as he got into his 30s and never again had to worry about getting a big payday.

2. Treatment of Tito on his way out.

3. Lowball of Lester.
4. Carl Crawford

5. Rusney Castillo.... Not to hi-jack the thread but how did this guy get a 7 year 72.5 million deal without ever proving himself? Just blind faith that his game would translate?
 

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I will eternally be grateful to this group...but...

6. Orsillo
This is easily top 2-3 for me
My #1 and it's not close. I'll never understand it and it has drastically reduced my enjoyment of NESN broadcasts. Nothing else ownership has done negatively has had such an impact.

Edited to add: such a first-world sports problem which just goes to show how amazingly fortunate we have been as fans.
 
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DennyDoyle'sBoil

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1. Pablo Sandoval. It was just idiotic, giving five years at big money to a guy who complained his previous team had the nerve to expect him to stay in reasonably good shape as he got into his 30s and never again had to worry about getting a big payday.

2. Treatment of Tito on his way out.

3. Lowball of Lester.
It's funny what one post-season can do, isn't it? Nobody even has considered the Lackey for Allen Craig and Joe Kelly trade in this list even though a couple years ago, when they were paying the last umpteen million on Craig's contract and Kelly was struggling it seemed awful.

Standing up to Tyler Austin and pitching great in the playoffs suddenly makes the Allen Craig experiment worth it.
 

pk1627

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Not sure why a particular trade or signing should be on the ownership. They hire a GM and let him do his job.

Henry has spent some money but this team has a preponderance of homegrown talent. He upgraded Fenway, hired some really talented GM's, and won 4 WS titles in 17 years. That's phenomenal. I love that he's going for it in 2019.

He managed to lose the best manager in baseball that is T. Francona, but we have Cora now so all is forgiven.
 

Danny_Darwin

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I guess I'd characterize my biggest issue with the Henry tenure less as one particular move and more that - for a while, at least - they ran a leaky ship. I can think of quite a few moves and non-moves that, regardless of their merits, played out in a sometimes ugly, messy, public fashion (Nomar, Manny, Pedro, A-Rod, Francona, Adrian Gonzalez, the Theo departure and return, surely more things I'm not thinking of). It does seem like it happens less frequently under Dombrowski, so I guess it could be attributed to Lucchino?

(Maybe this should be its own thread?)

(Edited to add examples)
 
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Plympton91

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I don't know if I'd go that far. In September of this year, there were serious questions as to whether Kelly should be on the postseason roster. But after October, it's certainly an easier pill to swallow now.

I mean, Cherrington should have done better than Kelly/Craig for Lackey.
What’s interesting is how many of the moves on the list are Cherington moves, but nobody has listed handing the GM to him without doing a real search after Theo left as a big mistake. That 2013 WS with all the mid-tier signings working out has bought him a lot of goodwill. Yet, this is a cautionary tale in not having a thorough and inclusive hiring process.
 

koufax32

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Not sure why a particular trade or signing should be on the ownership. They hire a GM and let him do his job.
The Lester fiasco seemed to be driven by ownership concerns.

The Crawford deal was made in the context of ownership wanting to make a splash and jumpstart sagging fan interest.

Am I remembering these correctly? If so, those disasters are all on them.
 

John Marzano Olympic Hero

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What’s interesting is how many of the moves on the list are Cherington moves, but nobody has listed handing the GM to him without doing a real search after Theo left as a big mistake. That 2013 WS with all the mid-tier signings working out has bought him a lot of goodwill. Yet, this is a cautionary tale in not having a thorough and inclusive hiring process.
You know, I never thought about it like this but your right. Cheering Ron was overmatched in a lot of his job responsibilities. Why didn’t the Sox brass recognize that?

The Sox ownership should bear some criticism for elevating Cherrington. Though I’m not sure where I’d put that on the (short) list of dumb things they’ve done.
 

Adrian's Dome

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The Lester fiasco seemed to be driven by ownership concerns.

The Crawford deal was made in the context of ownership wanting to make a splash and jumpstart sagging fan interest.

Am I remembering these correctly? If so, those disasters are all on them.
At the end of the day, John Henry is not the one negotiating contracts. He may voice a preference or set a hard limit on payroll, but the actual numbers and signing of deals is on the GM.

Lowballing Lester was 100% on Cherington, which was also the direct cause for overpaying Price, so basically a double whammy. Not that Price has been bad, but Lester is comparable production wise and would've cost less money and years.
 

Sandy Leon Trotsky

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At the end of the day, John Henry is not the one negotiating contracts. He may voice a preference or set a hard limit on payroll, but the actual numbers and signing of deals is on the GM.

Lowballing Lester was 100% on Cherington, which was also the direct cause for overpaying Price, so basically a double whammy. Not that Price has been bad, but Lester is comparable production wise and would've cost less money and years.
I liked Lester a lot.... didn't love him but really liked him. I do think they lowballed him... but I'm not sure he was the guy to get paid. He still wasn't really Ace Level to me and I was hoping they would've broken the bank for Scherzer instead that offseason- who truly has been a horse and a no. 1 all this time and worth the contract (in the context of course of the stupid amount ML baseball players get paid....). Lester had a great post-season and had some very good seasons prior... but he had consistency issues (not as extreme as Buchholz) and many of us were hoping to deal him for Cole Hamel at one point.
I wasn't bummed they lost him- just wish Ben was able to get a better return. I never understood the '14 sale MO. Felt unfocused
 

Sausage in Section 17

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Eovaldi...YES!!!


Full hijack....

Wasn’t the Lackey trade essentially a mutual quickie divorce on the heels of the beer and fried chicken fiasco? Sort of lumped in with the Tito firing, but I think Lackey didn’t want to be here, or play for free after hurting his elbow (per his contract )and winning us the WS.

We can sit here and say we shoulda paid Jon Lester, but it’s hard to say Price’s contract was a mistake in hindsight.

And they never should have let Orsillo go.
 

John Marzano Olympic Hero

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Full hijack....

Wasn’t the Lackey trade essentially a mutual quickie divorce on the heels of the beer and fried chicken fiasco? Sort of lumped in with the Tito firing, but I think Lackey didn’t want to be here, or play for free after hurting his elbow (per his contract )and winning us the WS.

We can sit here and say we shoulda paid Jon Lester, but it’s hard to say Price’s contract was a mistake in hindsight.

And they never should have let Orsillo go.
Chicken and beer was 2011 and Lackey was traded in 2014. He had redeemed himself in the eyes of many Sox fans with his 2013 playoff performances.

He was pitching pretty well for Boston when he got moved.
 

sezwho

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4. Carl Crawford

5. Rusney Castillo.... Not to hi-jack the thread but how did this guy get a 7 year 72.5 million deal without ever proving himself? Just blind faith that his game would translate?
I get the perspective, but for me Castillo doesn’t make the list. I actually harbor a fascination for an alternative reality where he didn’t get trapped in the minors by his salary and had a somewhat more normal development path opportunity.

Anyway, please carry on with the Eo thread morphing into a top ten list of things we don’t like about ownership :)
 

dhappy42

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I get the perspective, but for me Castillo doesn’t make the list. I actually harbor a fascination for an alternative reality where he didn’t get trapped in the minors by his salary and had a somewhat more normal development path opportunity.

Anyway, please carry on with the Eo thread morphing into a top ten list of things we don’t like about ownership :)
I don’t want to further sidetrack the thread, so I hope there’s a quick, short answer to this question: Are there other MLB players trapped in the minors by big contracts or is Castillo unique in that regard? Seems to me it be in the MLB’s interest (and just the right thing to do) to have some kind of mechanism to prevent this from happening.
 

Red(s)HawksFan

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I don’t want to further sidetrack the thread, so I hope there’s a quick, short answer to this question: Are there other MLB players trapped in the minors by big contracts or is Castillo unique in that regard? Seems to me it be in the MLB’s interest (and just the right thing to do) to have some kind of mechanism to prevent this from happening.
Kei Igawa?

Obviously not current, but another case like Castillo's where he was outrighted off the 40-man and became stuck in minor league limbo until his contract expired.

There should never be another case like Castillo's because it is no longer possible to outright a player with a contract like his and have it removed from the team's luxury taxable payroll.
 

chawson

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I don’t want to further sidetrack the thread, so I hope there’s a quick, short answer to this question: Are there other MLB players trapped in the minors by big contracts or is Castillo unique in that regard? Seems to me it be in the MLB’s interest (and just the right thing to do) to have some kind of mechanism to prevent this from happening.
I believe the Diamondbacks buried Yasmany Tomas in the minors with a 2/$32.5M contract.
 

judyb

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Castillo probably would have gotten a chance here and there if they hadn't changed that rule, because they could have outrighted him again if it wasn't worth keeping him on the 25, his salary only would have counted against the luxury tax for the time he was actually on the 40.
 

lexrageorge

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I'll tend to leave the GM mistakes (signing Sandoval, Crawford, Castillo) at the foot of the GM. Sure, ownership probably signed off on each of them, and may even have encouraged those signings in some cases ("Win in more exciting fashion"). But it's up to the GM to execute, and part of that is convincing ownership why signing a certain player is a good or bad idea.

Not exactly sure where to pin the Lester lowball: We know Cherington was GM, and it's really up to the GM to make the case if ownership is pushing back. At the same time, Henry was making noise about how signing players over 30, especially pitchers, is nearly always a bad investment. Then a few months later, Cherington makes a market offer to Lester that was just slightly topped by Theo and the Cubs. So, if I was to list the mistakes made by ownership:

1.) The treatment of Francona. Tito was going to be fired; Henry and Lucchino wanted him out for some reason. Now, we may not know all the reasons and the back stories, and the move may have been best for both parties (Francona seemed to be dealing with a lot towards the end). But the manner in which his exit occurred, and the following leaking of damaging information to the Bob Hohler, was disgraceful.

2.) The hiring of Valentine. Lucchino had Valentine pegged as the guy they were going to hire since mid-2011.

3.) Not naming Theo to be VP of Baseball Operations. Yes, Theo made mistakes, as has every GM in baseball. But there was no reason to him to continue to be subservient to Lucchino.

Maybe they could have found a better GM than Cherington. But, as much as he is derided here, Cherington did keep the prospect core alive long enough to bear fruit, whereas other GM's may have traded Betts and Benintendi for middle relief help.

The good news is that when mistakes were made, the ownership team took corrective action as opposed to doubling down on the same strategy.
 

TheoShmeo

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1.) The treatment of Francona. Tito was going to be fired; Henry and Lucchino wanted him out for some reason. Now, we may not know all the reasons and the back stories, and the move may have been best for both parties (Francona seemed to be dealing with a lot towards the end). But the manner in which his exit occurred, and the following leaking of damaging information to the Bob Hohler, was disgraceful.
I think it's interesting that Sox fans seemingly universally pin the Hohler source as Sox ownership.

I can understand why that would be so.

On the other hand:

- Hohler never revealed his sources so we have no actual confirmation. I would not expect him to do so, of course. I'm just saying we have no Deep Throat reveal here so it's open to question.

- Whatever one thinks of Henry, LL and Werner, they are not dumb men, and anyone with a brain would know that the reaction would be terrible. Really on two levels. One, because they would look so petty. Two, because whatever was ascribed to Tito happened on their watch; if he was using drugs and doing whatever else Hohler wrote, it behooved them to intervene in some way or help make the situation better, and they did not succeed in doing that. For PR conscious guys like these owners, I have some trouble believing they would not do the math in advance. Maybe Charles Steinberg wasn't on the job then but I can't believe he would not have objected (if they needed any help).

- Players who did not like Tito might have had an incentive to trash him. I know the popular refrain is that everyone loved Tito but that was a craptastic year. It's at least possible that one or more of the players had a problem with how he handled things. The ironic thing, to me, about the Hohler piece is the outrage over how Tito was treated on the way out has completely overshadowed that the Manager's performance might have been, and probably was, a contributing factor in the meltdown. Not the only factor; but one of many. Francona was such a sympathetic figure after Hohler that whatever percentage of the blame he deserved got immediately reduced to zero for most fans. Maybe a player or two thought that was BS and felt like doing something about it.

- Theo Epstein was the architect of that team, for the most part. The epic team wide collapse on the field and the apparent breakdown in discipline in the clubhouse reflected badly on everyone involved, including Theo. Pinning blame on Tito would provide teflon to Epstein. As a guy on the way out the door, being able to pin responsibility elsewhere would be beneficial in talks with other teams. And as a shrewd guy, he had to know that the public would blame the owners, and ignore Theo.

- It's possible also that Tito's issues were widely known among the media and that Hohler had multiple sources for his story. Either including or not including the Trio. Of everything I have written, this seems most likely to me.

I'm not saying that any of the above is true. I have no idea, really. I am also aware that the Sox ownership had a reputation for trashing guys on the way out. Still, I think there are plausible alternatives to the narrative that most seem to take as gospel.
 

TheoShmeo

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I think the Rusney Castillo contract was the worst player related decision.

In the 2013 off season, they gave a boat load of cash to a player who had played in a league no better than AAA (I assume) who was injured and hit .274 in the season before and who had two good seasons in that league the prior years.

I'm sure he looked great on film. But as bad as the Sandoval deal was, at least that guy had enjoyed some success in the majors and was a money player in the post season. Not that I am justifying that deal.

I just see Rusney as a bigger reach.

I know the same could be said for any deal involving a player from Japan or Cuba, and some have worked out very well, of course.
 

Papelbon's Poutine

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Dice K and Rusney were obviously blunders but didn’t cost anything more than money. It’s not our money so who gives a shit.

They should have traded Youk and kept Beltre. Fine to go ahead with AGon deal or allow Rizzo to develop. Sticking with Youk was one of their biggest mistakes imho.

I think Cherington should have been left in development. Without getting into the ‘departure’ of Tito, we don’t know how it went down but we do know he had some affairs during his tenure and as much as I loved him, much like Theo, people have shelf lives. If the ownership had a part in him getting smeared on way out, shame on them, but I’m not entirely convinced that’s the case.

If hooked up to a lie detector I didn’t mind Valentine at the moment it happened. I thought they needed a distraction and he’d provide it with his personality. I was obviously way off base on that. I thought their allegiance to Farrell was worse, despite the ring.

All good I don’t have many complaints. Every ownership/FO is going to have its foibles. 4 rings garner a lot of forgiveness.
 

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I think it's interesting that Sox fans seemingly universally pin the Hohler source as Sox ownership.

I can understand why that would be so.

On the other hand:

- Hohler never revealed his sources so we have no actual confirmation. I would not expect him to do so, of course. I'm just saying we have no Deep Throat reveal here so it's open to question.

- Whatever one thinks of Henry, LL and Werner, they are not dumb men, and anyone with a brain would know that the reaction would be terrible. Really on two levels. One, because they would look so petty. Two, because whatever was ascribed to Tito happened on their watch; if he was using drugs and doing whatever else Hohler wrote, it behooved them to intervene in some way or help make the situation better, and they did not succeed in doing that. For PR conscious guys like these owners, I have some trouble believing they would not do the math in advance. Maybe Charles Steinberg wasn't on the job then but I can't believe he would not have objected (if they needed any help).

- Players who did not like Tito might have had an incentive to trash him. I know the popular refrain is that everyone loved Tito but that was a craptastic year. It's at least possible that one or more of the players had a problem with how he handled things. The ironic thing, to me, about the Hohler piece is the outrage over how Tito was treated on the way out has completely overshadowed that the Manager's performance might have been, and probably was, a contributing factor in the meltdown. Not the only factor; but one of many. Francona was such a sympathetic figure after Hohler that whatever percentage of the blame he deserved got immediately reduced to zero for most fans. Maybe a player or two thought that was BS and felt like doing something about it.

- Theo Epstein was the architect of that team, for the most part. The epic team wide collapse on the field and the apparent breakdown in discipline in the clubhouse reflected badly on everyone involved, including Theo. Pinning blame on Tito would provide teflon to Epstein. As a guy on the way out the door, being able to pin responsibility elsewhere would be beneficial in talks with other teams. And as a shrewd guy, he had to know that the public would blame the owners, and ignore Theo.

- It's possible also that Tito's issues were widely known among the media and that Hohler had multiple sources for his story. Either including or not including the Trio. Of everything I have written, this seems most likely to me.

I'm not saying that any of the above is true. I have no idea, really. I am also aware that the Sox ownership had a reputation for trashing guys on the way out. Still, I think there are plausible alternatives to the narrative that most seem to take as gospel.
I think it’s fair to blame LL. Not that I think he was a key source for Hohler — if he were, Shaughnessy would’ve gotten the scoop instead. But it’s not like the leakers were loyal to Theo or Tito; they obviously thought LL would be pleased when he read the story, or at least not pissed. This perception speaks volumes about his leadership as President of the organization.
 

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I think it’s fair to blame LL. Not that I think he was a key source for Hohler — if he were, Shaughnessy would’ve gotten the scoop instead. But it’s not like the leakers were loyal to Theo or Tito; they obviously thought LL would be pleased when he read the story, or at least not pissed. This perception speaks volumes about his leadership as President of the organization.
Maybe, maybe not. If I were in his shoes, if I was not the source, I would have been pissed because I would have known that I would be blamed. And because Tito's problems, once revealed, arguably reflected poorly on all of them for not better dealing with them.

As to LL's leadership, the Sox won 3 WS, including the first one in 86 years, on his watch. I think that's pretty fucking good leadership. All of my team's should have leaders who are as effective as him.
 

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There have been some bad acquisitions and departures, but they are easy to put aside when looking at the success over the past 15 years.

That said, to me the biggest blunder was how the Lester situation. They could have kept him for a relative bargain prior to the start of that season, then low balled him, then traded him away. In hindsight, the original numbers would have been a tremendous bargain for the team, and by now we'd be looking at a potential Hall of Fame career spent on one team.
 

lexrageorge

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Dice K and Rusney were obviously blunders but didn’t cost anything more than money. It’s not our money so who gives a shit.

They should have traded Youk and kept Beltre. Fine to go ahead with AGon deal or allow Rizzo to develop. Sticking with Youk was one of their biggest mistakes imho.
I disagree with Dice-K being a blunder. He was a serviceable 3/4 starter for 3 of his first 4 years here before injuries caught up to him. He was overpaid, but not by that much once you take out the posting fee. Rusney was a far bigger blunder.
 

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I disagree with Dice-K being a blunder. He was a serviceable 3/4 starter for 3 of his first 4 years here before injuries caught up to him. He was overpaid, but not by that much once you take out the posting fee. Rusney was a far bigger blunder.
Fair enough, I think reasonable minds can differ. I disagree on ignoring the posting fee, but again...

I think if not for the luxury tax ramifications, Rusney would have proven to be the equivalence as a 4th Ofer.
 

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There have been some bad acquisitions and departures, but they are easy to put aside when looking at the success over the past 15 years.

That said, to me the biggest blunder was how the Lester situation. They could have kept him for a relative bargain prior to the start of that season, then low balled him, then traded him away. In hindsight, the original numbers would have been a tremendous bargain for the team, and by now we'd be looking at a potential Hall of Fame career spent on one team.
At the risk of appearing to be or being overly defensive of ownership, I will nevertheless note that i never understood the “low ball” explanation for Lester leaving. In the real world, low ball opening offers happen all the time. To think Lester would effectively leave over that is to say the he had incapable agents who could not explain the reality that to him. I find that hard to believe.
 

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Fair enough, I think reasonable minds can differ. I disagree on ignoring the posting fee, but again...

I think if not for the luxury tax ramifications, Rusney would have proven to be the equivalence as a 4th Ofer.
Daisuke was a useful piece of a WS-winning squad, then followed it up with a great 2008 (which was an absolute fluke, but it still happened.)

That's far more valuable and important than potentially maybe being a 4th OFer if not for circumstance. The two aren't even in the same stratosphere.
 

Adrian's Dome

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At the risk of appearing to be or being overly defensive of ownership, I will nevertheless note that i never understood the “low ball” explanation for Lester leaving. In the real world, low ball opening offers happen all the time. To think Lester would effectively leave over that is to say the he had incapable agents who could not explain the reality that to him. I find that hard to believe.
Dude. Lester was very willing to take a reasonable hometown discount to stay and avoid free agency and they gave him a completely halfass offer. That'd piss anyone off.
 

bankshot1

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Not to diminish the work of DD, but I think the ownership's mishandling of the LL/Theo relationship and not allowing Epstein greater autonomy which led to his departure might be the mistake with the greatest long-term impact. I think Theo Epstein is one of those very special talents who come along far too infrequently, and should be nurtured and allowed to grow. Unfortunately Fenway was too confining for both LL and Theo to do their best work. And its a shame we only got the first 10 years of Theo's growing executive abilities.
 

TheoShmeo

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Dude. Lester was very willing to take a reasonable hometown discount to stay and avoid free agency and they gave him a completely halfass offer. That'd piss anyone off.
True. And then any agent worth his salt would explain reality to the player and would counsel him to counter. Especially if his client really wanted to stay where he was. Dude.
 

lexrageorge

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Jul 31, 2007
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True. And then any agent worth his salt would explain reality to the player and would counsel him to counter. Especially if his client really wanted to stay where he was. Dude.
Except that offer didn't really indicate a willingness on the part of the team to negotiate. It was absurdly low for a pitcher of Lester's talent.
 

Adrian's Dome

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True. And then any agent worth his salt would explain reality to the player and would counsel him to counter. Especially if his client really wanted to stay where he was. Dude.
That's not how reality works...like at all. If someone's willing to bend over to do you a favor, you do not begin negotiations by attempting to completely screw them over.

Any agent worth his salt would explain to his player their exact realistic worth, and anyone with a shade of baseball knowledge knew Lester was worth far more than 4/70 at that point in time.
 
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TheoShmeo

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That's not how reality works...like at all. If someone's willing to bend over to do you a favor, you do not begin negotiations by attempting to completely screw them over.

Any agent worth his salt would explain to his player their exact realistic worth, and anyone with a shade of baseball knowledge knew Lester was worth far more than 4/70 at that point in time.
Agree to disagree on that reality.

In all walks of business, opening bids are often ridiculously low and motivated parties still find ways to get deals done. The notion that Lester was turned off and that lead to the deal not getting done makes no sense. If Lester was trained on staying in Boston, he would have listened to his agent telling him that huge low balls are commonplace and the process would have continued.

Did it open the door for other teams? Maybe. But that again allows that Lester reacted emotionally to the first bid, even after his agents educated him.
 

Van Everyman

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Ownership blunders in this group are few and far between – this might be the best ownership group in all of sports when you combine titles, market pressure, media environment, the renovation of Fenway and the fact that they’ve been competitive almost every year.

Of course they aren’t infallible and have made their share of mistakes, tho, as posters have noted, they’ve tended to correct those mistakes in fairly short order.

Player Acquisitions:
1a) Crawford – this was an out and out disaster only mitigated by the fact we could dump him
1b) Sandoval – not as huge of a contract but one they had to eat (oh the irony), so just as bad on balance
2) Replacing Beltre with AGon– his career numbers show Beltre is the one that got away and given what he did the year he was here they should’ve recognized the value of ability to play in Boston, but Theo’s boner for AGon made him lose perspective. Giving up Rizzo and grinding Youk down in all this also a check mark against this.

Personnel
1a) Hiring Bobby the Fifth – just an awful decision again mitigated by the fact that they dumped him quickly
2) Hiring Grady – by all accounts they knew early on he was resistant to analytics, he never should have been here

Even still, I think the biggest “blunder” was an organizational dynamic that Henry failed to correct: his tolerance of far too much tension and drama between baseball operations the business side for far too long. I’m probably one of the biggest apologists on the board for Lucchino and I’m sure they had good reasons not to give a 30 year-old kid from Brookline the keys to the kingdom right away. But in retrospect Theo and Lucchino were never going to work out long-term once they won and the gorilla suit nonsense should have been the sign that needed to end – they were lucky to get Theo back.

That they moved Lucchino out only a few years after Theo left suggests to me that they recognized this after the fact – likely due to Cherington’s inability to manage up with Lucchino and the pitiful personnel decisions that resulted. That they’ve now installed what appears to be an organizational structure with a clear delineation of responsibilities—Dombrowski with baseball ops, Kennedy with everything else—suggests to me that they’ve learned their lesson here. And that they still managed to win so many titles during this dysfunction suggests that they are exceptional performers in just about every other aspect of the business.
 
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