The 5 Dumbest Moves in Franchise History

TheYellowDart5

Hustle and bustle
SoSH Member
Apr 16, 2003
9,276
NYC
Hard not to see the Mookie Betts trade as one of the five dumbest things this franchise has ever done.
 

E5 Yaz

Transcends message boarding
Lifetime Member
SoSH Member
Apr 25, 2002
90,017
Oregon
No list of the five dumbest/worst things the franchise has done is complete without Tony C Night
 

Smiling Joe Hesketh

Throw Momma From the Train
Moderator
SoSH Member
May 20, 2003
35,727
Deep inside Muppet Labs
This is interesting enough to break out into its own thread.

For me it's the horrible "Get those ********* off the field!" moment. Whether it was Eddie Collins, Tom Yawkey, or Joe Cronin, that was by far the lowest and stupidest point in this team's entire history. Not only did they pass on a chance to sign Black players, not only did they pass on a chance to sign JACKIE ROBINSON, but the cemented themselves a reputation as a racist hotbed that TO THIS VERY DAY continues to haunt the franchise.

That moment above led directly to Pinky Higgins calling reporters *******-lovers more than 2 decades later. The stain has never gone away.
 

Philip Jeff Frye

Member
SoSH Member
Oct 23, 2001
10,229
No list of the five dumbest/worst things the franchise has done is complete without Tony C Night
Very true. That game was nationally broadcast on Monday Night Baseball, wasn't it?

The later Tom Yawkey years combined with the Sullivan/Leroux interregnum are a good reminder that, whatever our frustrations with the current brain trust are, things could be worse. A lot worse.
 

Smiling Joe Hesketh

Throw Momma From the Train
Moderator
SoSH Member
May 20, 2003
35,727
Deep inside Muppet Labs
As for 5 moves:

- selling Ruth
- the above mentioned Robinson tryout fiasco
- The Kapstein triplets/not offering Fisk a contract in time
- Earl Wilson and the Winter Haven Elks club incident
- the Mookie trade

Honorable mention to Tony C night and trading away Reggie Smith.
 

soxhop411

news aggravator
SoSH Member
Dec 4, 2009
46,276
Very true. That game was nationally broadcast on Monday Night Baseball, wasn't it?

The later Tom Yawkey years combined with the Sullivan/Leroux interregnum are a good reminder that, whatever our frustrations with the current brain trust are, things could be worse. A lot worse.
the Dolan family and the Mccourts were finalists when the sox were sold back in 2001 right?

so yes, it could have been a lot worse..... Wonder if Mccourt would have run the sox into bankruptcy like he did with the dodgers

And the Dolan's..... I dont think much needs to be said of how that would have ended if he ended up owning the Sox (go ask NYK fans)
 

Rasputin

Will outlive SeanBerry
Lifetime Member
SoSH Member
Oct 4, 2001
29,421
Not here
I think it's pretty easy to argue the Jeff Bagwell trade was dumber than the Mookie trade. Bagwell's in the Hall of Fame. Mookie may never be. Bagwell wasn't on the verge of becoming a free agent. They got less for Bagwell than for Mookie.

I mean, it was a shitty trade and all, but lets have some perspective.
 

Smiling Joe Hesketh

Throw Momma From the Train
Moderator
SoSH Member
May 20, 2003
35,727
Deep inside Muppet Labs
Could you expand on "Tony C Night"?
In 1983, the Red Sox suffered their first losing season since 1966, and the rift among the ownership factions became public. On June 6, prior to a Monday night home game against the Detroit Tigers, the Red Sox planned a special benefit for stricken former star outfielder Tony Conigliaro, who had been incapacitated at age 37 by a heart attack in January 1982. Conigliaro's old teammates from the 1967 "Impossible Dream" Red Sox assembled for a pre-game ceremony, and a crowd of nearly 24,000 gathered, one of the largest gates at Fenway Park since Opening Day. Boston's television stations had crews in place to cover "Tony C Night."

Prior to the festivities, LeRoux called a press conference and announced that he and a majority of the team's limited partners, chiefly Badgett and Albert Curran, were exercising language in their partnership agreement to overthrow Sullivan and Yawkey and take command of the club. He announced a "reorganization of internal management" and appointed himself managing general partner, while bringing in former Red Sox general manager Dick O'Connell to replace Sullivan as head of baseball operations. Boston media immediately dubbed the gambit the "Coup LeRoux."
Basically Buddy LeRoux used the attending press coverage of the event to honor and fundraise for Tony C as an excuse to launch a hostile takeover attempt on the team.
 

AB in DC

OG Football Writing
SoSH Member
Jul 10, 2002
13,629
Springfield, VA
Bagwell trade has to be worse than the Betts trade, no?

At least we only lost one year of Betts' performance.

[edit: beaten by Rasputin]
 

curly2

Member
SoSH Member
Jul 8, 2003
4,887
Selling Babe Ruth to the Yankees.
Passing on Willie Mays
The 1945 sham tryout of Jackie Robinson
Selling Bernie Carbo to Cleveland in 1978 to give ABs to Bob Bailey, then having to give playing time to Garry Hancock when they needed outfielders. (Selling Reggie Cleveland early in the season to keep Allen Ripley and three catchers also came back to bite them).
Mookie Betts trade.

The Robinson sham tryout was absolutely horrific but I ranked it behind Mays. The "Get those ---- off the field line" has been disputed over who said it -- or if it was actually said -- and it would have taken actual guts and more principles to break the color line. Signing Mays after the color line had been broken was a no-brainer, would have given Ted Williams some pitches to hit after Korea and would have changed the course of the franchise and possibly the city of Boston.
 

dhappy42

Straw Man
Oct 27, 2013
15,725
Michigan
Basically Buddy LeRoux used the attending press coverage of the event to honor and fundraise for Tony C as an excuse to launch a hostile takeover attempt on the team.
A shitty thing to do but can we limit “the five dumbest moves” to actual player deals or, as in the cases of Robinson and Mays, non deals?

1. Selling Ruth
2. Passing on Willie Mays*
3. Mailing Fisk’s contract two days late
4. Bagwell trade
5. Betts trade

*I rank Mays higher than Robinson because the Red Sox actually signed Mays (for $4,500) then reneged on the contract. Can you imagine Williams, Mays and D.DiMaggio in the same OF?
 

Ale Xander

Hamilton
SoSH Member
Oct 31, 2013
72,440
Mac not using Stapleton in Game 6 or Clemens in Game 7

Fisk no contract

Lester lowball

getting rid of Dumbo

Letting Ted go to the Pacific, twice.

fake edit: Bagwell forAnderson

(Ruth is #1)
Don’t know specifics about Jackie and Willie but those could be 2 and 3
 

Ale Xander

Hamilton
SoSH Member
Oct 31, 2013
72,440
I think it's pretty easy to argue the Jeff Bagwell trade was dumber than the Mookie trade. Bagwell's in the Hall of Fame. Mookie may never be. Bagwell wasn't on the verge of becoming a free agent. They got less for Bagwell than for Mookie.

I mean, it was a shitty trade and all, but lets have some perspective.
Plus relievers are fungible
You don’t get rid of cost-controlled infielder with potential for that, especially a rare New Englander
 

Sandy Leon Trotsky

Member
SoSH Member
Mar 11, 2007
6,348
For fuck sakes this is ridiculous!!!!!
People here have lost their minds. MOOKIE WAS GOING TO FREE AGENCY. They got what they were able to trying to also unload Price and knowing that they basically had put themselves into a corner in negotiations because of the decisions of the preceeding direction. Fair or not... .the Mookie trade sucked but it's not dumb. Shit... at one point after his 2nd year half the board here wanted to trade him to the Mets!
 

Hank Scorpio

Member
SoSH Member
Apr 1, 2013
6,915
Salem, NH
I can give a pass on signing Crawford, Sandoval, and Hanley - as those moves all had at least somewhat of a reasonable expectation that they would work out.

The Price contract wasn’t the best return on value, but he gave us a couple of solid seasons and was a key guy in a Championsh

But the Chris Sale extension was an absolutely moronic move that should not have happened.

Sale had trouble down the stretch in 2017, and was shelved for a big chunk of the second half in 2018. It was pretty clear his arm was a ticking time bomb. He was horrible in 2019, and now, as we head into 2023, he’s barely pitched since.

Can’t really say I saw *this* coming, but after 2018, I didn’t think he was really going to be a 30 start, 180+ inning guy anymore.

At this point, I think we’d be lucky to get 75-100 innings out of him.

The decision ultimately falls on Dombrowski’s head. It’s hard to play “what if”, but if we had chosen one of:

- Trade Sale after 2018
- Trade Sale during 2019
- Let Sale walk after 2019

We’d have been in a better position to keep Betts, DD might still be here, Bloom might not be here, and maybe instead of Story, we extend Bogaerts for similar money, and we’re just hoping to extend Devers and find some rotation help.

Instead of, you know, letting everyone go and alienating the entire fan base, and from where I sit, the Chris Sale contract is the catalyst for everything happening now.

It’s not as bad as failing to keep Mookie, but it goes hand in hand with it.
 

JM3

often quoted
SoSH Member
Dec 14, 2019
14,283
Sure, let's relitigate this one last time...

I'm going to preface this by saying Mookie is my all time favorite Red Sox player & the whole thing made me sad, buuuuuut...

All we actually lost in the Mookie trade was 246 plate appearances (2.8 fWAR) in 2020 in what would have been a horrendous Red Sox season regardless.

Price sat out 2020, so the Dodgers only had to eat $32m of his contract. They also paid Mookie the prorated portion of his $27m arb salary, which is $10m.

So the Dodgers paid $42m for 246 Mookie plate appearances & 114 David Price innings (at 0.8 fWAR). The return for paying $42m for 3.6 fWAR should be...negative...as each WAR should cost less than $11.7m on the open market.

Yes, it hurts because the Dodgers were able to resign Mookie at a reasonable rate...but the trade technically makes sense even if they did it for nothing because their books were so screwed up by DD's all-in approach.

So they took the best offer on the table which was apparently the Dodgers offer. In the past 3 seasons they have received a total of 5.1 fWAR from Verdugo at a total cost of $4.8m, pure unadulterated crap from Jeter Downs (-0.3 fWAR last season & he's gone from a consensus top 100 prospect to being a terrible baseball player), & not much from Colton Wong (0.1 fWAR last season).

They have 2 years of control on Verdugo left & like 5 more years of control on Wong. So bottom line:

Red Sox give up 3.6 fWAR and save $42m
Red Sox receive 4.9 fWAR, 2 more years of Verdugo, 5 more years of Wong, & pay about $6m

On the other hand...in 1990 Larry Andersen pitched a very good 22 innings for the Red Sox, earning like 0.8 fWAR...and Jeff Bagwell went on to earn 22.1 fWAR during his 4 arb years at a total cost of $3.5m before signing a giant 4/$27.5m contract. So the 2 trades really aren't comparable.

Also, Babe Ruth was purchased by the Yankees for $125k & then went on to put up 150.1 fWAR for the Yankees over the next 15 seasons...
 

Leather

given himself a skunk spot
SoSH Member
Jul 18, 2005
28,451
Mac not using Stapleton in Game 6 or Clemens in Game 7

Fisk no contract

Lester lowball

getting rid of Dumbo

Letting Ted go to the Pacific, twice.

fake edit: Bagwell forAnderson

(Ruth is #1)
Don’t know specifics about Jackie and Willie but those could be 2 and 3
I know Lester was well liked and a nice home-grown player, but... really? I always felt like winning in 2018 kind of put this one to rest.

Heck, off the top of my head, trading Lynn was probably a bigger mistake.
 

Mooch

Member
SoSH Member
Jul 15, 2005
4,494
The decades long institutional failure of the Red Sox organization to do anything about Donald Fitzpatrick. And that goes beyond "dumbest" into a whole other realm of unforgivable negligence and evil.
 

Mugsy's Jock

Eli apologist
Lifetime Member
SoSH Member
Dec 28, 2000
15,069
UWS, NYC
Not top five, but how about:

Letting George Scott wear those tight double-knit pants
Losing Don Orsillo
Tessie the Green Monster (I'm cool with Wally)
Jonathan Papelbon. Don't get me wrong, he was an elite closer and tremendous competitor for several years including a World Series winner, but if you're asking for "dumbest", Papelbon's gotta be in there.
 

Ale Xander

Hamilton
SoSH Member
Oct 31, 2013
72,440
Not top five, but how about:

Letting George Scott wear those tight double-knit pants
Losing Don Orsillo
Tessie the Green Monster (I'm cool with Wally)
Jonathan Papelbon. Don't get me wrong, he was an elite closer and tremendous competitor for several years including a World Series winner, but if you're asking for "dumbest", Papelbon's gotta be in there.
Part of the shtick
Papelbon isn’t dumb
Looking at his interviews post-retirement, he’s not dumb at all.
 

dhappy42

Straw Man
Oct 27, 2013
15,725
Michigan
For fuck sakes this is ridiculous!!!!!
People here have lost their minds. MOOKIE WAS GOING TO FREE AGENCY. They got what they were able to trying to also unload Price and knowing that they basically had put themselves into a corner in negotiations because of the decisions of the preceeding direction. Fair or not... .the Mookie trade sucked but it's not dumb. Shit... at one point after his 2nd year half the board here wanted to trade him to the Mets!
Can’t speak for others but for me “trading Betts” is shorthand for not extending his contract to avoid free agency… or making the highest FA bid like the Yankees just did with their face-of-the-franchise star.
 

snowmanny

Member
SoSH Member
Dec 8, 2005
15,667
Is selling Waite Hoyt, Carl Mays et al to the Yankees included in the Ruth transaction? Because Hoyt at least could be top 5.
 

bankshot1

Member
SoSH Member
Feb 12, 2003
24,652
where I was last at
I'll let you guys negotiate 1-5, but somewhere in the next 5-10 boners are trading Earl Wilson in 1966 (he won 22 for Detroit in '67) , the Sparky Lyle trade for a bag of ball and Danny Cater to some shitbag team south of us, and trading Fergie Jenkins after the '77 season for another bag of balls and he went 18-8 in '78.

I'd argue that Wilson and Fergie could have made significant contributions to a generally starting pitching needy Sox and might have delivered WS in '67 and '78.
 

E5 Yaz

Transcends message boarding
Lifetime Member
SoSH Member
Apr 25, 2002
90,017
Oregon
I'll let you guys negotiate 1-5, but somewhere in the next 5-10 boners are trading Earl Wilson in 1966 (he won 22 for Detroit in '67) , the Sparky Lyle trade for a bag of ball and Danny Cater to some shitbag team south of us, and trading Fergie Jenkins after the '77 season for another bag of balls and he went 18-8 in '78.

I'd argue that Wilson and Fergie could have made significant contributions to a generally starting pitching needy Sox and might have delivered WS in '67 and '78.
The Earl Wilson trade was especially repugnant

wiki: Howard Bryant's book Shut Out deals with Wilson's time at Boston. During spring training in 1966, Wilson had entered a bar in Florida with two white colleagues, Dennis Bennett and Dave Morehead, and was told "we don't serve niggers here". Wilson left the bar and took the issue to Red Sox management, but was told to forget about it and not speak to the press. This was too much for the proud Wilson, who revealed what had happened to the media. He was traded to the Detroit Tigers for outfielder Don Demeter and pitcher Julio Navarro. Wilson subsequently hit more home runs for Detroit as a pitcher than Demeter, while Navarro never pitched a game for Boston.
 

trekfan55

Well-Known Member
Lifetime Member
SoSH Member
Oct 29, 2004
11,587
Panama
The Betts trade qualifies, not for value but for the move itself. When it was made no one knew COVID was going to happen.

The Sox should have kept Betts and then try to sign him. That is why it's dumb.

The problem right now is that the Sox will apparently not sign those big years/big money contracts. That is another subject in and of itself.

So as dumb moves go

1. Babe Ruth for sure (although he hits less homers with Fenway being home).
2. Willie Mays. He was signed.
3. Bagwell (for the value, and the FO was told Bagwell was good)
4. Betts (trading him at all)
5. Lowballing players who might have signed before hitting FA

BTW Papelbon does not really count. He was going to FA and did go to FA and did not last the contract in Philly.

Edit to add: Not sure if ot would have worked, but not having Rollie Fingers actually pitch so the Commisioner could not void the trade
 

shaggydog2000

Member
SoSH Member
Apr 5, 2007
11,482
This is interesting enough to break out into its own thread.

For me it's the horrible "Get those ********* off the field!" moment. Whether it was Eddie Collins, Tom Yawkey, or Joe Cronin, that was by far the lowest and stupidest point in this team's entire history. Not only did they pass on a chance to sign Black players, not only did they pass on a chance to sign JACKIE ROBINSON, but the cemented themselves a reputation as a racist hotbed that TO THIS VERY DAY continues to haunt the franchise.

That moment above led directly to Pinky Higgins calling reporters *******-lovers more than 2 decades later. The stain has never gone away.
The Celtics of the 50s and 60s broke just about every meaningful barrier related to black athletes in Basketball, and were at the forefront of racial integration in sports. They were still called a white washed team that symbolized bad racist Boston in the 80's. I don't think anything the Sox did would have changed that either.
 

In my lifetime

Well-Known Member
Lifetime Member
SoSH Member
Dec 18, 2003
959
Connecticut
1. Selling Ruth
2. Reneging on Mays contract
3. Mailing Fisk contract 2 days late
4. Trading Bagwell for Anderson
5. Leaving a hobbled Buckner in the game and Stapleton on the bench reportedly so Buckner could be on the field to celebrate to WS win
6. Sparky Lyle trade for Cater

Honorable Mention:
Hiring Grady
 

pk1627

Well-Known Member
Lifetime Member
SoSH Member
May 24, 2003
2,514
Boston
This is a team that went 86 without a championship. It started with the Ruth trade but all the idiotic things by Yawkee and his racist mgmt are the top 25. Then letting Francona go.
 

YTF

Member
SoSH Member
1. Selling Ruth
2. Reneging on Mays contract
3. Mailing Fisk contract 2 days late
4. Trading Bagwell for Anderson
5. Leaving a hobbled Buckner in the game and Stapleton on the bench reportedly so Buckner could be on the field to celebrate to WS win
6. Sparky Lyle trade for Cater

Honorable Mention:
Hiring Grady
IMO Buckner being "hobbled" had nothing do do with the error. He was there, the ball went through his legs.
 

Delicious Sponge

Well-Known Member
Lifetime Member
SoSH Member
Dec 23, 2003
1,350
Boston
IMO Buckner being "hobbled" had nothing do do with the error. He was there, the ball went through his legs.
If Buckner fields that cleanly who knows if he’s able to throw out Wilson. The whole inning was an absolute nightmare.

Top 5 have been well covered but in the top 10 somewhere is Grady letting a clearly gassed Pedro go back out to pitch and then leaving him in. I’ve never seen any moment in sports where it was obvious to every sentient being on Earth (I’m including dogs and fish on this list) that this shouldn’t be happening and yet Grady stuck with his plan.
 

bstoker7

Member
SoSH Member
Aug 22, 2006
150
South Jordan, UT
Can’t speak for others but for me “trading Betts” is shorthand for not extending his contract to avoid free agency… or making the highest FA bid like the Yankees just did with their face-of-the-franchise star.
He was never a free agent. They offered a massive extension and he explicitly stated he was going year to year and testing free agency. He extended with the Dodgers only after Covid changed the world.
 

Leather

given himself a skunk spot
SoSH Member
Jul 18, 2005
28,451
Not a top 5 but letting Carlos Pena walk after 2006 probably cost them the 2008 World Series.
 

sezwho

Member
SoSH Member
Jul 20, 2005
1,951
Isle of Plum
..snip…
Top 5 have been well covered but in the top 10 somewhere is Grady letting a clearly gassed Pedro go back out to pitch and then leaving him in. I’ve never seen any moment in sports where it was obvious to every sentient being on Earth (I’m including dogs and fish on this list) that this shouldn’t be happening and yet Grady stuck with his plan.
Yeah, Grady non-decision decision is up there in 5-10.

Also the Panda contract is not bottom 5, but it was a kind of jump the shark moment for me in the Dombrowski era.