The 5 Dumbest Moves in Franchise History

Sausage in Section 17

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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.
Almost all the other moves are those of the front office. Little leaving Pedro in has to be the dumbest on field move in Red Sox history.
 

Adirondack jack

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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.
Without delving into the days the Titanic was afloat, we can mostly all recount the days when we could count, on one hand, after the 4th of July, the amount of pitches squared up on Papelbon. For a few years he was about as lights out as one could ever hope a closer to be. But by the time free agency rolled around, he wasn't that guy. Paps ain't close to this list of top 5 franchise mistakes. When he was good though, it was like Grant Fuhr in a big game in the 1980s playoffs. During that window I wouldnt pick another
 
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mikeford

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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.
Its definitely this and quite frankly other than Ruth there is a strong argument the rest of the top 5 is all during the Yawkey tenure.

HOWEVER

I am going to nominate hiring Booby V for this topic.
 

Mugsy's Jock

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Without delving into the days the Titanic was afloat, we can mostly all recount the days when we could count, on one hand, after the 4th of July, the amount of pitches squared up on Papelbon. For a few years he was about as lights out as one could ever hope a closer to be. But by the time free agency rolled around, he wasn't that guy. Paps ain't close to this list of top 5 franchise mistakes. When he was good though, it was like Grant Fuhr in a big game in the 1980s playoffs. During that window I wouldnt pick another
Let me be clear — I adored Papelbon. He was nails and he was fun. He just came off as a dummy (we all remember the jig with a empty Budweiser case on his head), but @Ale Xander tells me it was all an act and I’m happy to believe it.
 

WestMassExpat

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There's a big difference IMHO between just bad luck (i.e., lamenting poor performance after no prior bad track record) versus just really shitty decision making.

Former, I can let the Crawford trade slide (at least out of the top five) -- posted a .300/.349/.443 slash line the three seasons prior, was coming off a 7-bWAR season, and had excellent SB numbers. I think the Panda signing is mitigated out of my top-five for roughly the same reason. And maaaaaybe it's unfair to judge the Bagwell trade with the benefit of hindsight (he had two seasons in the minors at the time, albeit very good ones, but at least there's an argument for the stretch run with Anderson -- wasn't there? I was like 7 at the time).

On the latter, it's obvious. Selling Ruth, being racist, the Fisk contract debacle. I'd put failing not signing Betts as a FA in this camp (I mean, the trade is another argument). Pay the man his money or what the heck are we doing? I'd feel the same about Devers.
 

simplicio

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I'm glad at least a few people here are pushing back on the Mookie bs. God I wish any post with his name got automodded and sent straight to its own subforum at this point.

The Panda/HanRam acquisitions kinda count for me because they happened so close together and both guys were so clearly in decline and had no logical role with the team. It's wasn't like Crawford where future performance could have reasonably been expected.
 

John Marzano Olympic Hero

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Panda was a Cherington signing. Dombrowski had nothing to do with Panda or Hanley.

And if we’re being charitable, neither did Cherington.
 

Swedgin

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Without delving into the days the Titanic was afloat, we can mostly all recount the days when we could count, on one hand, after the 4th of July, the amount of pitches squared up on Papelbon. For a few years he was about as lights out as one could ever hope a closer to be. But by the time free agency rolled around, he wasn't that guy. Paps ain't close to this list of top 5 franchise mistakes. When he was good though, it was like Grant Fuhr in a big game in the 1980s playoffs. During that window I wouldnt pick another
Pretty sure he was referring to Paplebon's actual intelligence, not any transaction related issues.
 

nvalvo

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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.
Six years of Bagwell vs. one of Betts.
 

Smiling Joe Hesketh

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IMO Buckner being "hobbled" had nothing do do with the error. He was there, the ball went through his legs.
He finally spoke about it years later when he took a look at the replay. He was wearing a very old, soft glove, and when the ball hit it the glove was so unstiff that it gave way and didn’t stop the ball at all. And upon replay he’s right, you can see the glove bend back as the ball hits it.

Buckner was done dirty.
 

John Marzano Olympic Hero

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He finally spoke about it years later when he took a look at the replay. He was wearing a very old, soft glove, and when the ball hit it the glove was so unstiff that it gave way and didn’t stop the ball at all. And upon replay he’s right, you can see the glove bend back as the ball hits it.

Buckner was done dirty.
Dave Stapleton should have been in there just like he was for every close playoff game that the Sox were winning. Buckner was only in there because McNamara thought Buck deserved to be on the field when the team won.

Mac never admitted that until it was way too late and Buckner had to live with years of constant abuse. McNamara was a rotten manager and I don’t think he was much better of a person.

Bill Buckner, Calvin Schiraldi, Bob Stanley and Rich Gedman alll deserved better.
 

moondog80

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Six years of Bagwell vs. one of Betts.
Not just that...supposedly they didn't realize Bagwell's power (4 HR) was being suppressed by his environment...the whole team hit only 31 HR that year. Bagwell was still 5th in the league in SLG. Only 10 guys in the league had double digit HR.

22 year old Bagwell went 333/422/457 in AA. That guy would not get traded today, not for a middle reliever anyway.

Ruth was obviously a terrible decision, but I can't completely kill it because it was such a low information age, I don't know that anyone knew any better. Comparing that to Bagwell is like someone who smoked 2 packs a day in 1910 to just 1 a day now.


https://www.baseball-reference.com/register/league.cgi?id=37a77879
 

John Marzano Olympic Hero

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Screw that. We gave up real talent, but Boddicker was great in 88 and gave us two full years.
Not only that but Schilling didn’t get his act together until five years and two organizations later. Anderson wasn’t much until around the same time.

Boddicker was a really good number two for the Sox. I’d make this trade every day.
 

nighthob

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1) Hiring Eddie Collins
2) Hiring Joe Cronin
3) Hiring Pinky Higgins
4) Hiring Billy Herman
5) Hiring Don Zimmer
6) Hiring John McNamara
7) Hiring Butch Hobson
8) Hiring Joe Kerrigan
9) Hiring Grady Little
10) Hiring Bobby Valentine
 

Philip Jeff Frye

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A good contemporary account of the Coup LeRoux on Tony C night, courtesy of Sports Illustrated.

It's amazing to read how small the millions of dollars cited are, particularly in the context of the nine figure contracts thrown around willy nilly in the last few weeks.
 

Red(s)HawksFan

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If Buckner fields that cleanly who knows if he’s able to throw out Wilson. The whole inning was an absolute nightmare.
No way he'd have thrown Wilson out because there was no one to throw to. Stanley wasn't there or anywhere close. So the real question is whether he could have beaten Wilson to the bag, and the answer to that is a resounding no. Really the only thing that Buckner fielding the ball cleanly does is extend the game another batter: 1st and 3rd with two outs and HoJo at the plate.
 

John Marzano Olympic Hero

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Really the only thing that Buckner fielding the ball cleanly does is extend the game another batter: 1st and 3rd with two outs and HoJo at the plate.
So are you saying that you wouldn't be okay with extending the game another batter? Because anything is better than what transpired.

I'm not sure what you're arguing here.
 

Toe Nash

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Ruth was obviously a terrible decision, but I can't completely kill it because it was such a low information age, I don't know that anyone knew any better. Comparing that to Bagwell is like someone who smoked 2 packs a day in 1910 to just 1 a day now.
Ruth was (probably) sold to fund a non-baseball venture and had just led the league in runs scored, RBI, HR (major league record), and was 8th in BA. He was also a top pitcher. The Sox were then horrendous for the next 15 years. You don't need Fangraphs to understand his talent.
 

Big Papi's Mango Salsa

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Trading Betts isn't even close to a top 5 dumbest move for me. He was going to be a Free Agent. He wanted to leave unless he was over-paid to stay. I can also totally understand not betting on his body type / profile long term, and, ostensibly the idea was to use the financial flexibility of getting below the luxury tax penalties to keep guys like Bogaerts and Devers (or so I thought).

I'm not going to address things from before the 1980s because I don't know enough about the context of the moves. Though obviously any decision based on racism (the Yawkeys) is going to be exceptionally high on the list.

Anyway, not necessarily in order, but these were all far dumber than trading Betts.

1) Not giving Theo whatever it took to stay. Ownership stake. Firing Lucchino. Renaming it Casablanca Park. Whatever.
2) The way the Francona experience ended. Awful from a baseball standpoint, horribly disappointing from a "human decency" stand point.
3) Grady Little playoff bullpen usage.
4) Bobby. Valentine.
5) Bagwell for Anderson.
6) The Crawford contract.
7) Signing Renteria instead of Cabrera.
8) Dealing Manny for Bay (I still think we win the 2008 World Series with Ortiz and Manny in the middle of that lineup).
9) Not extending Bogaerts.
10) Not extending Lester (this is less dumb than Bogaerts because we were able to trade Lester, but still dumb).

I disagree so very much with approximately 99% of the decisions Bloom has made since November 2021, and I can't stress this enough, but trading Betts actually made sense. What we did after that, not so much.
 

RIFan

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A few honorable mentions:
1. Trading Reggie Smith (Wise was key to '75 and Carbo had his moments, but Smith shouldn't have been the guy to go.)
2. Firing Joe Morgan to promote Butch Hobson from AAA
3. Giving Joe Kerrigan a mulit-year contract instead of doing a full manager search
4. Letting Mo Vaughn walk
5. Letting Roger walk
 

Red(s)HawksFan

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So are you saying that you wouldn't be okay with extending the game another batter? Because anything is better than what transpired.

I'm not sure what you're arguing here.
Not arguing anything other than pointing out that they weren't putting Wilson out whether Buckner fielded the ball cleanly or not. Of course extending the game another batter is a good thing in that spot. My confidence that Stanley gets out of it and the Sox get another chance at bat from that point is still kinda low though. I think the Mets eventually bring Knight home regardless. We just have a different scapegoat (perhaps deservingly) than Buckner in such a case.
 

pedro1999mvp

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I love Mookie and he was my favorite player at the time, but I can at least see why they did it at the time. The return sucked for a player of his caliber, but they got payroll flexibility by dumping Price. The deal was bad, but it pales in comparison to the Bagwell trade. To me, that's the worst trade we've ever made. Other things are bad like selling Ruth, the Robinson tryout, failing to offer Fiske a contract on time, but trading Bagwell for Larry Andersen was really dumb.
 

BuellMiller

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A few honorable mentions:
1. Trading Reggie Smith (Wise was key to '75 and Carbo had his moments, but Smith shouldn't have been the guy to go.)
2. Firing Joe Morgan to promote Butch Hobson from AAA
3. Giving Joe Kerrigan a mulit-year contract instead of doing a full manager search
4. Letting Mo Vaughn walk
5. Letting Roger walk
Was letting Mo go on its own, and in retrospect, that bad? Obviously, he was a popular player and great hitter for the 6 previous seasons. But he only really played 3 more full seasons (injured in the middle), and put up OPS+ of 119, 115, and 114. The replacement at 1B/DH (Daubach/Stanley) did just as well in 1999 (2000 was another story, but paying Mo premium money to 115 OPS+ is probably not worth it).
Of course, that 1998-1999 offseason was a mess otherwise (signing Offerman's OBP to replace Mo (which wasn't that bad of an outcome in 1999 before dropping off precipitously), getting strung along/used by Bernie Williams, and then not adding anything else to the lineup that still featured Darren Lewis in CF, as well as only adding washed up Mark Portugal and mediocrity Pat Rapp to supplement Pedro in the rotation (and thus relying again on injury prone Saberhagen to be #2).
 

Shaky Walton

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The Rusney Castillo signing deserves mention in the conversation, even if it's just a footnote. It's clearly not of the order of magnitude of many of the moves that have already been mentioned.

But they gave a boatload of cash to a guy whose performance in Cuba had been uneven and who had been hurt for much of his time there. It made no sense when he was signed and was nothing but wishcasting over an athletic looking guy and a desire to be in on the Cuban experience.

And for me, Grady leaving Pedro on the mound after the first bad thing happened in the bottom of the 8th was as dumb as it gets. Hell, sending him out there at all was insanity, but he should have known to remove his starter after any negative result occurred. Critically, Grady should have also known that Pedro was materially worse that year after 100 pitches (Theo's crew had reminded him), Pedro had given up a homer to Giambi in the 7th, the environment at the Toilet was incredibly intense, leaving Pedro spent, and Pedro had sat on the bench after pointing to the heavens while walking off the mound to end the 7th, took off his cleats off and let the adrenaline leave his body. It was screamingly obvious that Grady was begging for disaster with playoff ready Timlin and Williamson in the wings.

If the Sox had not won the title in 2004, Grady's Boner would live in much bigger infamy.
 

curly2

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Almost all the other moves are those of the front office. Little leaving Pedro in has to be the dumbest on field move in Red Sox history.
If you want to talk about moves made by a manager, it's up there, along with Joe McCarthy starting Denny Galehouse in a one-game playoff and John McNamara not putting in Dave Stapleton for defense. But the dumbest thing ever done on the field is absolutely this.

 

strek1

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Maybe the thread should have been "dumbest transactions" so we didn't spill into all the on field stupidity too. All this failure in one place is hard to stomach. LOL
 

Rovin Romine

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Maybe the thread should have been "dumbest transactions" so we didn't spill into all the on field stupidity too. All this failure in one place is hard to stomach. LOL
Ultimately we're talking about the possibility of winning.

Bad transactions can decrease your chance of winning, but it's sometimes hard to quantify unless the player is a sure-thing. Meaning they had no choice about staying, and were overwhelmingly likely to have dominated in such a way as to shift the fortunes of the club. Bagwell was traded in 90, came up in 91, and was dominant. If the Sox had him in 91-96(ish) at 3B, 1B or DH. . .I think that qualifies.

Bad moves early in a season are likewise tough to predict, but I'm sure there are some "invisible" choices that derailed seasons.

But face-planting at the finish line? The cause-and-effect possibilities narrow.
 

Hyde Park Factor

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So are you saying that you wouldn't be okay with extending the game another batter? Because anything is better than what transpired.

I'm not sure what you're arguing here.
I think the point was that even if Buckner makes the play, that doesn't give the Sox the win.

Speaking strictly for me, I've always felt like people think that since the error lost the game for the Sox, a clean play gives them the win.
 

TheYellowDart5

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Maybe the thread should have been "dumbest transactions" so we didn't spill into all the on field stupidity too. All this failure in one place is hard to stomach. LOL
As the (sort of) thread starter, yeah, my thinking was more "dumbest front office/ownership decisions." Managerial moves is a whole other thing.
 

Rasputin

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Ruth was (probably) sold to fund a non-baseball venture and had just led the league in runs scored, RBI, HR (major league record), and was 8th in BA. He was also a top pitcher. The Sox were then horrendous for the next 15 years. You don't need Fangraphs to understand his talent.
He was also an incredible pain in the ass.
 

Marciano490

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He finally spoke about it years later when he took a look at the replay. He was wearing a very old, soft glove, and when the ball hit it the glove was so unstiff that it gave way and didn’t stop the ball at all. And upon replay he’s right, you can see the glove bend back as the ball hits it.

Buckner was done dirty.
Why did he use a shitty glove? Sounds more Bad News Bears than Boston Red Sox.
 

Didot Fromager

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Getting into the weeds maybe, but these continue to befuddle me.
1) Not putting Hobson on the disabled list in 1978
2) It wasn't just Ruth - it was Ruth, Wally Schang, Everett Scott, Joe Dugan, Waite Hoyt, Carl Mays, Sad Sam Jones, Joe Bush, and Herb Pennock. Half the starting lineup and the entire starting rotation of the 21-24 pennant winning Yankees were on the Red Sox in 20-21. Worse than the Yankees and As in the 50s.
3) Haywood Sullivan as a player, GM, and owner
4) not resigning Adrian Beltre
5) Bronson Arroyo for Wily Mo Peña (22 bWar v -1 bWar)
 

simplicio

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Oh yeah Beltre is a good one. Plus if we'd given him 5+ years after 2010 we never would have blundered into the Panda signing.