High-Class Problems: Worst Blunders of the Henry Era

bankshot1

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Seems to me Lester acted rationally by responding to the low-ball offer by 1) rejecting it and 2) telling the Red Sox he would not let it distract his on-field efforts and would not negotiate during the regular season. (ie hello free-agency-Jonny Lester LLC is open for business). If Red Sox management's goal was to resign Lester they failed spectacularly.
 

The Talented Allen Ripley

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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.
I negotiate salaries for a living. Generally I'm always trying to get a candidate to accept the lowest offer he/she will be comfortable with, but that never, ever starts by throwing out a figure that's 50% - 60% of what they're seeking (and what the market has established they're worth).

If the lowball approach is so reasonable, why not offer 30%? 20%? You can always move up, right?

What that ridiculous initial offer to Lester did was cause him to think of a baseball life in anything other than a Red Sox uniform. Up until then, he assumed he'd re-sign and was happy to at a discount, but that half-hearted attempt by the Sox made him think, "Gee, maybe I might end up playing somewhere else." (I'm paraphrasing, but Lester's thoughts on the process are on the record, I'll see if I can dig up some quotes.) And once he began to envision leaving was possible, the more he warmed up to the idea of hitting free agency.

That lowball offer was a colossal mistake.
 
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Papelbon's Poutine

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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.
He had a 4.79 ERA over 2 postseasons (including loss to a 5 in 2007). I’m not exactly sure that was worth $100M+. Ymmv. Let’s agree on the overall he wasn’t worth the expenditure?
 

lexrageorge

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He had a 4.79 ERA over 2 postseasons (including loss to a 5 in 2007). I’m not exactly sure that was worth $100M+. Ymmv. Let’s agree on the overall he wasn’t worth the expenditure?
He also drove in 2 key runs that helped blow Game 3 in Colorado wide open. And was the winning pitcher in Game 7 of the ALCS. It was a 3-2 game when he left, so he did the job in a key spot there.

I'll take a World Series title over the payroll efficiency title any day.
 

TheoShmeo

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I negotiate salaries for a living. Generally I'm always trying to get a candidate to accept the lowest offer he/she will be comfortable with, but that never, ever starts by throwing out a figure that's 50% - 60% of what they're seeking (and what the market has established they're worth).

If the lowball approach is so reasonable, why not offer 30%? 20%? You can always move up, right?

What that ridiculous initial offer to Lester did was cause him to think of a baseball life in anything other than a Red Sox uniform. Up until then, he assumed he'd re-sign and was happy to at a discount, but that half-hearted attempt by the Sox made him think, "Gee, maybe I might end up playing somewhere else." (I'm paraphrasing, but Lester's thoughts on the process are on the record, I'll see if I can dig up some quotes.) And once he began to envision leaving was possible, the more he warmed up to the idea of hitting free agency.

That lowball offer was a colossal mistake.
So I don’t negotiate salaries for a living and can’t argue on that basis. But I do negotiate in many other contexts and in my experience, if the counter party really badly wants the deal, an initial extremely low offer does not ruin things. I’ve seen ridiculously low openers end up resulting in a transaction many times. If the counter party is somewhat lukewarm or even just open to something different to start with, then a lowball can indeed sour things.

I don’t see this as all or nothing. I agree that they should not have low balled Lester to that extent. My point is that I think that Lester wanted Boston to begin with less intensity than he publicly admits. I think that if he was really strong on his desire to stay, that the parties would have found a way to work through it.

Lester’s comments shed some light, for sure, but what people say for public consumption isn’t always exactly what they mean.

I could be wrong and recognize that my view is not at all widely held. What I’m most convinced of is that the almost linear analysis — lowball effectively caused him to leave — is almost certainly simplistic and that there are more layers. Again, I know most differ with me and that’s fine.
 

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So I don’t negotiate salaries for a living and can’t argue on that basis. But I do negotiate in many other contexts and in my experience, if the counter party really badly wants the deal, an initial extremely low offer does not ruin things. I’ve seen ridiculously low openers end up resulting in a transaction many times. If the counter party is somewhat lukewarm or even just open to something different to start with, then a lowball can indeed sour things.

I don’t see this as all or nothing. I agree that they should not have low balled Lester to that extent. My point is that I think that Lester wanted Boston to begin with less intensity than he publicly admits. I think that if he was really strong on his desire to stay, that the parties would have found a way to work through it.

Lester’s comments shed some light, for sure, but what people say for public consumption isn’t always exactly what they mean.

I could be wrong and recognize that my view is not at all widely held. What I’m most convinced of is that the almost linear analysis — lowball effectively caused him to leave — is almost certainly simplistic and that there are more layers. Again, I know most differ with me and that’s fine.
I've actually always believed that both Lester and the team were ready to part ways and move on. The low ball was extreme, but in the end, Lester got to leave looking like the good guy, the team took the heat for the split, and both parties got what they wanted. I've never really had a problem with any of it.
 

The Talented Allen Ripley

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So I don’t negotiate salaries for a living and can’t argue on that basis. But I do negotiate in many other contexts and in my experience, if the counter party really badly wants the deal, an initial extremely low offer does not ruin things. I’ve seen ridiculously low openers end up resulting in a transaction many times. If the counter party is somewhat lukewarm or even just open to something different to start with, then a lowball can indeed sour things.
It's one thing to egregiously lowball an offer on a house, or on a business service/transaction. It's entirely another to do so on salary offer, because there's a level of personal assessment there that doesn't exist in the other scenarios.
 

lexrageorge

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An extreme lowball offer to buy in a business transaction (or extreme highball offer to sell something) typically signals a fairly large disconnect in expectations somewhere as opposed to a starting position for negotiations. Such an offer does not normally result in a counter, but usually a restructuring of the transaction (or a complete walk away).

As noted, salary negotiations are even trickier due to the natural emotion involved.
 

InstaFace

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It's one thing to egregiously lowball an offer on a house, or on a business service/transaction. It's entirely another to do so on salary offer, because there's a level of personal assessment there that doesn't exist in the other scenarios.
I think you've got the better of this debate. I don't know if it was a top-3 blunder on their part, but I'm sold that not making a credible starting offer was definitely a blunder.

For my money the worst decisions were:

1. Cherington, from which most bad personnel decisions sprung. Can't believe they didn't run a real search. Of course, they didn't really run a real search when they promoted Theo after his San Diego time, so maybe they figured they had it nailed.

2. Sandoval. Hanley Ramirez had plenty of support here at the time of signing, and had deserved his top-10 MVP finish only two years prior. Panda, although 3 years younger than HRam, had way more tread on the tires, hadn't had a good season at the plate in 4 years, and there was plenty of ready foresight here about his likely trajectory. We overpaid in years and in AAV, to the wrong player - it's really a 3-part mistake, removing any one of which would have greatly mitigated its impact on our last few years.

3. Letting Pedro go, put his 2005 on our team instead of Matt Clement and I bet we repeat

3. OK, more seriously, it's probably Carl Crawford. I still can't believe the Dodgers ate that contract just to get Adrian Gonzalez.

I was really saddened by them losing the best manager in baseball, but it was just a bad relationship at that point and nothing they could have done would have repaired it, I don't think. Both sides needed a change. Our rebound relationship sucked, but we got over it.
 

gedman211

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At least there was a job opening for Sandoval. Signing Hanley in order to put him in the outfield was perhaps the stupidest organizational move I've ever seen. The guy had never even shagged a fungo before, and they stick him in front of the Monster.

A lot of the moves mentioned here can be filed under "Pink Hat" decisions- moves made to boost the entertainment value and bring in casual fans and in turn drive NESN's advertising revenue. Crawford was supposed to be exciting for his athleticism. Sandoval was the team Mascot. Hanley was the wacky goofball slugger a-la Manny. O'Brien had the gravitas of a national media presence. Valentine was the witty firebrand. Dice-K had the exotic Gyro-ball. Lucchino was just building another hit sit-com for the baseball agnostic, because the Die-Hards will tune in no matter what.
 

Van Everyman

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Lucchino is a lawyer. Werner is the Cosby alumnus.

I do agree that something was funky about Cherington. While we may never know what actually happened, my operating assumption has been that Theo more or less knew how to manage up—either because he had a good relationship with Henry to keep Larry in check or maybe just knew how to settle with Larry when things got heated—while Cherington had no such ability.

So when Lucchino suggested they hire Bobby V or acquire Panda or Hanley, Cherington just didn’t have the juice to push back. And as a result you had a really Jeckyl and Hyde tenure of some moves that seemed designed for the long-term—holding on to prospects—others that seemed like weird short-term boosts to gin up ticket sales.
 

section15

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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.
I have to disagree with you - because in many walks of life, if a seemingly insulting offer is conveyed, it possibly leads to an immediate breakdown in negotiations.

JL approached the Red Sox in good faith and knew what he wanted, and was willing to take less than open market value, and they turned and insulted him.

At the end of it all, they essentially matched the Cubs' offer, but he turned it down. The Cubs were a contender as they were (and are today) -- and the Red Sox were in turmoil at the end of the 2014 season. About the same money, a lot better baseball environment at the time. He and his family didn't mind moving on, they were going to a better place (at the time).

Now I will tell you what I think was equally as big of a blunder

- the Red Sox daring Mookie Betts to go to arbitration at the beginning of the 2018 season. Yes, he waved it off, and won his case, getting $1.5 million more than he was willing to settle for at the table, by all reports.

THAT BLUNDER MAY COME BACK TO HAUNT THEM. (bold caps). And if the Sox are not doing well on the field when he enters unrestricted free agency, that may be a motivator for him to go. The money will be SOMEWHERE for Mookie, but his loyalty has been challenged.
 

section15

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I've actually always believed that both Lester and the team were ready to part ways and move on. The low ball was extreme, but in the end, Lester got to leave looking like the good guy, the team took the heat for the split, and both parties got what they wanted. I've never really had a problem with any of it.

I don't think the Red Sox got what they wanted. They wound up attempting to match the Cubs' offer, and John Henry even flew down to Atlanta (JL's home now) to try to convince him to stay. Even in the final days of negotiations, some reported that he was coming back.

And although there was a last place finish in 2014 for the Sox - with his departure, we had another cellar finish in 2015,. I don't think that's what the Red Sox wanted out of all of this.
 

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I don't think the Red Sox got what they wanted. They wound up attempting to match the Cubs' offer, and John Henry even flew down to Atlanta (JL's home now) to try to convince him to stay. Even in the final days of negotiations, some reported that he was coming back.

And although there was a last place finish in 2014 for the Sox - with his departure, we had another cellar finish in 2015,. I don't think that's what the Red Sox wanted out of all of this.
We really don't have any idea what truly went on, so it's all just conjecture on our part, and each believing what we choose to believe.
 

Van Everyman

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I was going to say, the whole “The Red Sox lowballed and insulted Jon Lester with $70M so he left” narrative ... do we know for sure this happened? The only real article I remember citing this as if it were gospel initially was a piece touting Henry’s steadfast belief that the Sox don’t pay for pitchers over 30 – perhaps it was Seth Mnuchin in the New Yorker? But I feel like this evil lowball offer mandated on high by Lucchino has gone into lore as fact. Are we sure it was?
 

Papelbon's Poutine

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As fact? No, do we ever? But it was reported by multiple outlets and that he asked for a Homer Bailey level deal and told no. I don’t think it’s a stretch to believe that either they lowballed him or trading him pissed him off. I think Bob has it 50/50 correct, if he wanted to stay he would have. But by that point, ship had sailed and Cubs were able to overpay more due to their roster construction.
 

jaytftwofive

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I never thought Grady Little was that bad except for the Game 7 ALCS debacle. He won 93 and 95 games compared to Jimy Williams. Without the Pedro mistake, they go to the WS and win or lose he saves his job so I guess it was a blessing what happened because we get Tito and the rest is history. I would say Sandoval no.1. 1A in hindsight is not keeping ADRIAN BELTRE! and trading Rizzo. I never understood why they didn't try to keep this all star and now future HOF. They could have had Beltre and Rizzo instead of A-Gon and Crawford. I"m surprised more people aren't remembering the off season of 2010.
 

jaytftwofive

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I never thought Grady Little was that bad except for the Game 7 ALCS debacle. He won 93 and 95 games compared to Jimy Williams. Without the Pedro mistake, they go to the WS and win or lose he saves his job so I guess it was a blessing what happened because we get Tito and the rest is history. I would say Sandoval no.1. 1A in hindsight is not keeping ADRIAN BELTRE! and trading Rizzo. I never understood why they didn't try to keep this all star and now future HOF. They could have had Beltre and Rizzo instead of A-Gon and Crawford. I"m surprised more people aren't remembering the off season of 2010.
Sorry, I saw somebody did have this up above.
 

Sandy Leon Trotsky

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Theo had/has the "pinkie" problem. He's always obsessed over certain players and was willing to overlook their faults and occasionally couldn't see the pros in what he had. Crawford is exhibit 1a, Gonzalez 1b, Beltre 2a and his Rizzo/Lars Anderson preference is 2b.
Could've resigned Beltre... kept Youk at 1B for another year.... brought in Rizzo. That little stretch seemed like a perfect example of lateral movements
 

chawson

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My real answers are Beltre and Sandoval, but I’ll throw another one out there for the sake of discussion.

Failing to sign Yasmani Grandal when the Sox drafted him out of high school in the 27th round in 2007 stuck out to me at the time. Can’t find reports about how much the Sox offered, but Grandal didn’t consider it an “acceptable offer,” and he went to school and was drafted 12th overall by the Reds in 2010.

It’s a massive hindsight-is-20/20 thing. There are signability guys who go back to school every draft, but apart from Rizzo in the sixth round, the Sox got nothing from that draft, and could have allocated more $ to Grandal to get him signed.

Since his team control years neatly come to an end this offseason, it provides an easy look. Grandal was worth 14.2 fWAR from 2014-18, over which time Sox catchers ranked 29th of 30th in MLB. Had Grandal been in the system, maybe the Sox trade Swihart for Hamels or part of a package for Donaldson? Maybe they take Snell instead of Swihart in the 2011 draft? Revisionist history, but interesting to think about.
 

Red(s)HawksFan

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Theo had/has the "pinkie" problem. He's always obsessed over certain players and was willing to overlook their faults and occasionally couldn't see the pros in what he had. Crawford is exhibit 1a, Gonzalez 1b, Beltre 2a and his Rizzo/Lars Anderson preference is 2b.
Could've resigned Beltre... kept Youk at 1B for another year.... brought in Rizzo. That little stretch seemed like a perfect example of lateral movements
What was his Rizzo/Anderson preference? Are you inferring that because he traded Rizzo, he preferred Anderson? I don't think that was the case. He dealt Rizzo because Anderson's value had plummeted by that point. Anderson wouldn't have gotten the deal for Gonzalez done. That's why Rizzo was part of the deal (along with the presumption that he would be blocked by Gonzalez for the foreseeable future anyway).
Failing to sign Yasmani Grandal when the Sox drafted him out of high school in the 27th round in 2007 stuck out to me at the time. Can’t find reports about how much the Sox offered, but Grandal didn’t consider it an “acceptable offer,” and he went to school and was drafted 12th overall by the Reds in 2010.

It’s a massive hindsight-is-20/20 thing. There are signability guys who go back to school every draft, but apart from Rizzo in the sixth round, the Sox got nothing from that draft, and could have allocated more $ to Grandal to get him signed.
Really, failing to sign a 27th round pick stood out as a big miss at the time? Don't most unsigned players drafted that late prefer to go to college anyway? Seems like it would have to be a significant overpay to convince a 27th rounder to forgo college. Especially if they can go to school for free for three years, improve their stock, and get a first round signing bonus like Grandal (and dozens and dozens of others before him) did. We're talking the difference between a few thousand dollars (in the 27th round) and hundreds of thousands, even millions of dollars a couple years later.

Major league baseball is littered with players who didn't sign out of high school and improved their draft position in college. While it's a fun "what if" to play noting those players that go on to good careers, but in no way should any such player be considered a miss held against the GM who drafted him the first time around.
 

chawson

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What was his Rizzo/Anderson preference? Are you inferring that because he traded Rizzo, he preferred Anderson? I don't think that was the case. He dealt Rizzo because Anderson's value had plummeted by that point. Anderson wouldn't have gotten the deal for Gonzalez done. That's why Rizzo was part of the deal (along with the presumption that he would be blocked by Gonzalez for the foreseeable future anyway).


Really, failing to sign a 27th round pick stood out as a big miss at the time? Don't most unsigned players drafted that late prefer to go to college anyway? Seems like it would have to be a significant overpay to convince a 27th rounder to forgo college. Especially if they can go to school for free for three years, improve their stock, and get a first round signing bonus like Grandal (and dozens and dozens of others before him) did. We're talking the difference between a few thousand dollars (in the 27th round) and hundreds of thousands, even millions of dollars a couple years later.

Major league baseball is littered with players who didn't sign out of high school and improved their draft position in college. While it's a fun "what if" to play noting those players that go on to good careers, but in no way should any such player be considered a miss held against the GM who drafted him the first time around.
By “at the time” I mean it stuck out to me for some reason that year, when I didn’t really understand the draft and follow process like I do now. I remember reading some hype piece about Grandal in 2007 and the matter became Sox lore trivia to me.

Your take is accurate. It’s more of a “what if” than a grievance against the FO, but there aren’t a lot of those guys the Sox drafted in the last 12 years. Bregman’s another one (who reportedly the Sox were talking to and went with Marrero instead), and so was Brandon Belt (as a pitcher).
 

Flunky

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Hanley still helped them to two ALDS's.

Sandoval and Crawford are like hood ornaments for the "let's forget" years. The reason why this thread title is what it is, is because the team woke up from both large mistakes to world championships. A lot of team's fans get to have that bad taste in their mouths for a lot longer. They don't even get a playoff appearance after such blunders.
 

Yelling At Clouds

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Sure. Lots of shit was widely reported at the time.
This is kind of what I was talking about before. I don't always buy some of the things people say about LL around here - seems he gets a lot of blame for things that went wrong and very little credit for what went right - but it sure seems like we don't hear this constant drip of whatever incremental progress they're making (or not making) on negotiations with whatever player. I wonder if part of the reason that Dombrowski is perceived as acting so boldly and decisively is because he's better at keeping all of this stuff in house (and in exchange, he seems a lot more candid in on-record interviews). As with most things that I think of as being differences between Dombrowski and his predecessors, there very well may be an explanation for this that's more because of circumstances than philosophy - he seems to make fewer moves overall, and surely part of that is because he inherited a solid roster. But I feel like I didn't hear any "PRICE TO BOSTON???" rumors before he signed. Same with Sale beyond reports of an attempted trade at the deadline. JD was admittedly a little different, but even that I feel like there was no news until there was news. Maybe I just pay less attention these days; it's certainly possible I'm remembering incorrectly.
 

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The hometown discount ship sailed when they traded him.
Okay, let me make sure I understand this. They traded him to a playoff team instead of having him play out the string in last place, and also strengthened the team for the future. And this so enraged him that the hometown discount, which may or may not have ever really existed in the first place, now really, really didn't exist.
 
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MtPleasant Paul

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We are missing a big thing in this discussion of how smart the Red Sox have been. Hey, I like John Henry because he's astute but I love him for his WILLINGNESS TO SPEND MONEY. And this franchise has not always - maybe not usually - spent money.

They were not exactly big spenders under Jack(?) Quinn in the miserable 1921-1933 period, under Haywood Sullivan and Buddy Leroux after 1978 (losing Tiant, Fisk, Lynn and many more) , under the parsimonious Yawkey Foundation (I remember from the Nineties media discussions of the Red Sox as a middle market team) until the Damon and Ramirez signings in 2002 were done to ready the team for sale.. And what about the alleged cornucopia that was Yawkey? Except for the splurge for Lefty Grove, Joe Cronin, and Jimmy Foxx up to 1938, there wasn't much - a few hundred thousand to the Browns for Stephens and Kinder in 1948, a couple of bonus babies in the early 50's and $100K for Ken Harrelson in 1967. My recollection of the Sox from the 50's into the 60's is that Yawkey's interest in the team was sporadic and his checkbook was often closed.

There's a reason why we didn't win until Henry got here and it has as much to do with money as with smarts.

The open checkbook, the willlingness to spend whatever it takes - that's what Yankee fans understood when George Steinbrenner passed away and why they poured out to commemorate him. Instead of carping that Henry & co. wasted money, let's be grateful that he was willing to spend in the first place.

The day is going to come, - I think maybe in the next decade - when John Henry - for estate purposes or whatever - is going to cash out. Hopefully he doesn't demand an extortionate settlement from the new owners, like Jeffrey Loria did in Miami, that will cripple the franchise for years to come. Hopefully, we're not going to be lamenting the absence of his generous hand at the pursestrings.
 

brandonchristensen

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This is kind of what I was talking about before. I don't always buy some of the things people say about LL around here - seems he gets a lot of blame for things that went wrong and very little credit for what went right - but it sure seems like we don't hear this constant drip of whatever incremental progress they're making (or not making) on negotiations with whatever player. I wonder if part of the reason that Dombrowski is perceived as acting so boldly and decisively is because he's better at keeping all of this stuff in house (and in exchange, he seems a lot more candid in on-record interviews). As with most things that I think of as being differences between Dombrowski and his predecessors, there very well may be an explanation for this that's more because of circumstances than philosophy - he seems to make fewer moves overall, and surely part of that is because he inherited a solid roster. But I feel like I didn't hear any "PRICE TO BOSTON???" rumors before he signed. Same with Sale beyond reports of an attempted trade at the deadline. JD was admittedly a little different, but even that I feel like there was no news until there was news. Maybe I just pay less attention these days; it's certainly possible I'm remembering incorrectly.
The early Theo years may have been loose lips in the organization, or it could have been Boston Red Sox fervor was at an all time high with the rivalry. Coverage on the A-Rod trade and the Cabin Mirror stuff, Dice-K, etc. etc. were round the clock coverage.
 

Red(s)HawksFan

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The early Theo years may have been loose lips in the organization, or it could have been Boston Red Sox fervor was at an all time high with the rivalry. Coverage on the A-Rod trade and the Cabin Mirror stuff, Dice-K, etc. etc. were round the clock coverage.
And the fervor was viewed as a feature that had to be fueled and kept going by certain wings of Sox management by any means necessary including leaks to the media. Lucchino was all about keeping the team in the headlines even through the winter while Theo was content with a little bit of quiet and calm in the off-season. That difference of opinion/approach was one of the tipping points that led to Theo donning the gorilla suit.
 

Sandy Leon Trotsky

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What was his Rizzo/Anderson preference? Are you inferring that because he traded Rizzo, he preferred Anderson? I don't think that was the case. He dealt Rizzo because Anderson's value had plummeted by that point. Anderson wouldn't have gotten the deal for Gonzalez done. That's why Rizzo was part of the deal (along with the presumption that he would be blocked by Gonzalez for the foreseeable future anyway).

.
My recollection of it was that the Padres preferred Anderson but Theo was a definite "no". Lars' value had not yet plumetted but there was some questions about his actual hitting ability. At the time, it was viewed that Gonzalez would be the 1st baseman (Youk goes back to 3rd.... far past his actual time he should have been viewed as being able to) for another year or two until Lars matured and would turn into the future long term 1B and Gonzalez would mostly DH. I could be wrong.... but I definitely was upset when it was Rizzo and felt like it was going to be a bad long term deal at the time. I loved Gonzalez but didn't like his long term health and cost. Either way... that whole Youk/Beltre/Gonzo/Rizzo situation felt like rearranging deck chairs and lateral moves, coupled with his Crawford obsession really turned me off to Theo and I was happy to see him leave- less so with Tito who I felt was left to try and make sense of Theo's garbage last few seasons without any of Theo admitting responsibility for the dysfunctional cluster he gave him. It's still amazing that Ben was able to maneuver those Theo blunders onto LA's dime and turn it into a WS a season later..... and then amazing that Ben turned right around and followed in Theo's mistake footprints
 

Van Everyman

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We are missing a big thing in this discussion of how smart the Red Sox have been. Hey, I like John Henry because he's astute but I love him for his WILLINGNESS TO SPEND MONEY. And this franchise has not always - maybe not usually - spent money.

They were not exactly big spenders under Jack(?) Quinn in the miserable 1921-1933 period, under Haywood Sullivan and Buddy Leroux after 1978 (losing Tiant, Fisk, Lynn and many more) , under the parsimonious Yawkey Foundation (I remember from the Nineties media discussions of the Red Sox as a middle market team) until the Damon and Ramirez signings in 2002 were done to ready the team for sale.. And what about the alleged cornucopia that was Yawkey? Except for the splurge for Lefty Grove, Joe Cronin, and Jimmy Foxx up to 1938, there wasn't much - a few hundred thousand to the Browns for Stephens and Kinder in 1948, a couple of bonus babies in the early 50's and $100K for Ken Harrelson in 1967. My recollection of the Sox from the 50's into the 60's is that Yawkey's interest in the team was sporadic and his checkbook was often closed.

There's a reason why we didn't win until Henry got here and it has as much to do with money as with smarts.

The open checkbook, the willlingness to spend whatever it takes - that's what Yankee fans understood when George Steinbrenner passed away and why they poured out to commemorate him. Instead of carping that Henry & co. wasted money, let's be grateful that he was willing to spend in the first place.

The day is going to come, - I think maybe in the next decade - when John Henry - for estate purposes or whatever - is going to cash out. Hopefully he doesn't demand an extortionate settlement from the new owners, like Jeffrey Loria did in Miami, that will cripple the franchise for years to come. Hopefully, we're not going to be lamenting the absence of his generous hand at the pursestrings.
This strikes me as entirely backwards. Sure the Red Sox had their share of cheap moments – ie, Fisk, etc. But their problem was rarely “failing to go the extra mile for their team” (as was memorably said)—there was no shortage of high priced flops in the pre-Henry era—but usually to spend that money wisely. Even since they’ve had their share of expensive mistakes, but they’ve been disciplined enough in the other aspects of their organization to weather them.
 

Rovin Romine

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I think we've seen some fairly drastic swings in performance that can't be put down to simply acquiring the right player/pieces so that their individual development arcs line up to produce winning season. Which is to say, I think the management's manager/coaching/special instructor decisions play an enormous role in the first and fifth place finishes in the Henry era.
 

The Talented Allen Ripley

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Okay, let me make sure I understand this. They traded him to a playoff team instead of having him play out the string in last place, and also strengthened the team for the future. And this so enraged him that the hometown discount, which may or may not have ever really existed in the first place, now really, really didn't exist.
Lester talked specifically about the impact of being traded after he signed with the Cubs. It didn't enrage him, but it opened his eyes to the fact that he could play for another team/city and it wouldn't be the end of the world. Up until then he assumed he'd be staying a Red Sox, because that's what he wanted and was willing to be flexible about it. Then he was traded, and once that mental threshold was crossed, he was open to the idea of exploring the free agent process to its fullest.
 

In my lifetime

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We are missing a big thing in this discussion of how smart the Red Sox have been. Hey, I like John Henry because he's astute but I love him for his WILLINGNESS TO SPEND MONEY. And this franchise has not always - maybe not usually - spent money.

They were not exactly big spenders under Jack(?) Quinn in the miserable 1921-1933 period, under Haywood Sullivan and Buddy Leroux after 1978 (losing Tiant, Fisk, Lynn and many more) , under the parsimonious Yawkey Foundation (I remember from the Nineties media discussions of the Red Sox as a middle market team) until the Damon and Ramirez signings in 2002 were done to ready the team for sale.. And what about the alleged cornucopia that was Yawkey? Except for the splurge for Lefty Grove, Joe Cronin, and Jimmy Foxx up to 1938, there wasn't much - a few hundred thousand to the Browns for Stephens and Kinder in 1948, a couple of bonus babies in the early 50's and $100K for Ken Harrelson in 1967. My recollection of the Sox from the 50's into the 60's is that Yawkey's interest in the team was sporadic and his checkbook was often closed.

There's a reason why we didn't win until Henry got here and it has as much to do with money as with smarts.
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You forget that there was a completely different set of rules as well. The RS (and Yankees) in 1976 purchased Fingers and Joe Rudi for a million each, only for Kuhn to reverse the trade/purchase 3 days later. The RS spent, under Yawkey, however they didn't typically spend wisely and they made more than their share of mistakes. I think the point of this thread is that the number of poor decisions made by Henry & Co. is that the number of mistakes made are few in the context of the thousands of personnel decisions per year.
 

Minneapolis Millers

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The post-'67 Sox were always close but usually a step or two away. IMO, they squandered the first 5 years of Pedro by failing to get him adequate running mates in the rotation. Henry/Epstein finally fixed that over Thanksgiving 2013. Then they got Beckett to pair with Schilling. Those were key "extra miles" that the prior admins never quite took.

But on Lester, I still think they screwed up. I thought at the time that they should have offered him slightly better than Wainwright's deal (since, you know, he beat Wainwright twice in the Series). Seemed like an obvious comp to me and one that would likely have made sense to Lester as a fair but discounted deal. Instead they went short on money and, more important, years. It just seemed like such poor negotiating that I assumed they really didn't prioritize keeping him. And then they ultimately signed Price for waaay more.
 
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reggiecleveland

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I don't care whose feet you lay it at, but Bobby Valentine was the worst move. Tito, Ferrell, Cora were light years better than he was. He didn't get out of spring training before he was flapping his gums about Jeter's play being a over rated, and talking about himself. He did not fit the corporate style of professionalism and protecting players from the media circus. The whole year leading up to the collapse of 2011 and the aftermath are the darkest point in Henry's ownership, even if you lay it on LL, JW was the owner and he let it happen. It was the only time I doubted the team would not stay a top level franchise. After Valentine was hired I thousght maybe Henry was bored with his new toy, and the Sox would go backwards.

Signing Crawford
The Theo exit mess
The leaking about chicken and beer, was worse than the actual chicken and beer
Laying the blame at the feet of Tito and the shredded arm of Lackey. (remember Tito was so enfeebled and drug addicted he would never manage again? SOmehow Cleveland cured him of his irreversible decline)
The over reaction of hiring Valentine.
 

JohntheBaptist

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Yeah, there were a number of blunders that were bad, but products of entirely human responses--responses to success, increased visibility, power struggles, sticking around in an intense environment. Sandoval was obviously a bad idea, for example, but you could squint and make a case (it was bad though, all around). Blunders for sure, though you just can't avoid a few of those.

But the Bobby Valentine hire was a joke from the moment it was announced. He'd been essentially out of baseball for years, was running a deli in Stamford, hadn't been rumored for MLB jobs anywhere for a reason. It was a stupid PR reaction to a clubhouse upheaval and was embarrassing from the jump. The idea to give the appearance of whipping the clubhouse into shape after the chicken and beer stuff--whatever, fine. But Bobby Valentine as a solution was an absolute joke and made the team look rudderless and without any vision or handle on the direction things were going.
 

m0ckduck

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When the thread question was posed, I thought it was about moves that could be directly laid at the feet of ownership, not GM player personnel moves. If we're expanding it to include all organizational mistakes, I'll add getting outbid on Jose Abreu. That seemed to me like an obvious win at the time for the Whtie Sox. Abreu's put up 18.7 WAR so far, five years into a 6/68MM contract. Plus, it apparently caused Cherington to come down with Kei Igawa Syndrome and go hard after Rusney Castillo.

Could've resigned Beltre... kept Youk at 1B for another year.... brought in Rizzo. That little stretch seemed like a perfect example of lateral movements
Hats off to you if you knew these were bad moves at the time. I consider this to be 'hindsight 20/20' territory, especially the Beltre move. At the time, Youkilis looked like the better 3B option. Even after Beltre's huge 2010 season, Youkilis had still out-WARed hm over the last four seasons. Beltre had a reputation of being an up-and-down player who delivered huge contract years but mixed results otherwise. Add in the fact that Youkilis was a homegrown guy on a good contract and it seemed far-fetched that the Sox would jettison him. Keeping both players seemed to be a poor use of resources when you could slide Youkilis across to 3B and get 1B production for cheaper than it would cost to sign Beltre on the open market. When he signed with Texas for 5/$80M, I recall the general consensus on this board being, "For that money, you can have him." That he turned out to be one of the best FA signings of his generation, and to have one of the best post-30 careers of his generation, is just bad luck.

The Gonzalez trade is more questionable. At the time, it seemed to me risky but defensible. I recall feeling that we were giving away a lot of assets for the privilege of essentially paying Gonzalez his open-market value. Then again, the organization badly wanted a middle-of-the-order bat and it was much more likely that Anthony Rizzo became Lars Anderson than Anthony Rizzo.
 
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Sandy Leon Trotsky

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Thanks for the hat tip. I don’t think I was the only one though.... Youk has been great at 1B. Moving him back to 3B to make room for Gonzalez was itself a lateral move. And I was very bullish on Rizzo over Anderson for the prior year.

The Abreu deal was awkward though.... IIRC... Chicago signed him during the ALCS in ‘13. I remember feeling that the Sox should grab him but worried about the message that would have sent to Napoli
 

section15

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Lester talked specifically about the impact of being traded after he signed with the Cubs. It didn't enrage him, but it opened his eyes to the fact that he could play for another team/city and it wouldn't be the end of the world. Up until then he assumed he'd be staying a Red Sox, because that's what he wanted and was willing to be flexible about it. Then he was traded, and once that mental threshold was crossed, he was open to the idea of exploring the free agent process to its fullest.
A lot of truth in what you say. It's like being dumped by a girlfriend who demands you stay in her life, and you're down and out about it, and then you end up meeting someone else.

The timeline

10/13 = Red Sox win World Series. JL is the best Sox pitcher in the mix.

3/14 - :JL declares his love for Boston and the Red Sox and states he'd like to negotiate a future long-term contract. Red Sox counter by making an offer he can't accept.

4/14 - as the regular season beings, JL states that he will put the negotiations off until season's end. Avoid the distraction.

7/14 - comes the All Star break. Widely reported = Red Sox are desperate to have him sign a contract. Widely known = Red Sox are having a season in which they will end up in the cellar, and the only proven pitching performer is .. JL.

Widely reported = JL says "no means no. Let's talk in November."

mid 7/14 - JL pitches his last victory for the Sox a 6-0 gem against the Royals at Fenway. Later in the week he has a 2-0 lead to be blown by the pen, vs. the Rays, a no-decision for JL. His last Red Sox appearance.

late 7/14 - Sox 13 games out, having lost 9 out of 11, down from 7.5 down at his last win. and on their way from a first-to-worst classic season, trade JL to Oakland for their best player (Cespedes), a move that Sox fans understand, Athletics fans are riled over it. Classic scene has JL and wife Farrah leaving Fenway in their SUV, John Henry wishing him luck and expressing wishes that he'll be back next year.

10/14 - JL loses WC game in KC. Oakland is out. After the WS, JL is a free agent.

11/14 - Discussions ensue with several teams, including the Red Sox. Comparable offers, allowing for tax differences, are made by the Giants, Cubs, and Red Sox. Others make offers, but the Lester camp concentrates on these three.

12/6/14 - John Henry is reported, by multiple sources, to travel to Lester's Georgia home for a 1-on-1 session to try to convince him to stay. Offer now is supposedly six years, and in line with what other teams are proposing. Lester had his Newton home on the market, but even if it sold, he now has the money for an upgrade. The ESPN story reports =

"After meeting with the Red Sox last week, Lester's agent, Seth Levinson, noted the "great respect" the team accorded Lester, who has repeatedly said he is not necessarily signing for top dollar but looking for the place he finds most comfortable."

This gives the Sox, and their fans, some hope that the hatchet from bad negotiations in March are buried. It could also lead to something more ominous.

12/15/14 - Lester signs with the Cubs, opting to rejoin Theo Epstein and Jed Hoyer, favorite catcher David Ross goes with him.

12/16/14 - Christmas at Fenway is a completely depressing event. Instead of greeting fans inside the Royal Rooters club, team officials opt to conduct their interviews outside, out of view and avoiding those who chose to attend.

October 2015 - Cubs finish 90-72, 3rd, winning record. Win wild-card, NLDS, but lose in four straight in the NLCS to the Mets. In the meantime, the Sox finish 78-84, in the cellar again, and replace GM Ben Cherington in August.

October 2016 - Cubs win World Series. Red Sox finish 1st in the AL East and take an immediate dixie , 3-0, to the Indians.

Note the most significant report above = "looking for the place he feels most comfortable."