Worst Contracts In Pro Sports History

[TheHorde]

That is around the range the Sox reportedly offered before being traded. Again I do think he wanted to go to free agency to help the players and that it probably would’ve taken $35M-40M a year for 8+ years for him to sign an extension before Covid. In the end, the David price and Chris sale deals made offering that much almost impossible. They’d be committing ~$90M to those 3 players coming off a disappointing year they weren’t really close to making the playoffs, with very little talent in the farm system. Kind of similar to the Yankees last year, except without one of the top farm systems to go out and make a Juan Soto like trade or even just supplement at trade deadlines. In retrospect, yes mookie still would’ve been worth that, but I don’t blame the Sox for moving him.

I think Bloom should’ve taken on some salary dumps in those years after trading Mookie (look for one of those Carl Crawford / Adrian Gonzalez type trades that the dodgers/sox also made except be on the other end of it), or ate the Price contract to get some better prospects in the trade. But clearly Red Sox ownership wanted to cut payroll so that wasn’t happening.

The blame lies with John Henry and FSG. They would have had 2 years of luxury tax penalties but would have come out the other side after Price’s contract expired. They’re cheap. That’s the bottom line. There’s no excuse to not spend on a frontline starting pitcher this off-season and the fan base is definitely paying attention.

 

[Deepster]

Every year, I post about Bonilla's contract because every year (and thread like this) gets it wrong.

1) Every team has deferred deals just like this one. Ken Griffey Jr was the 4th highest paid Red last season (2023) and gets 3.6m a year.

2) That deal, at the time, used the saved cash to sign Mike Hampton, Derek Bell and Todd Zeile, who all helped the Mets to the National League pennant in 2000. That alone is worth it.

 

[Inyatkin]

Did you edit this and take Pujols name out? I was going to tell you why the Pujols contract was always a terrible one.

I did. I was thinking Kawhi and wrote Pujols. Guess I had huge Angels contracts on my mind.
You could argue Pujols was defensible given his performance, but it was also clear as day at the time he could never live up to those numbers for the duration

 

[Scoe]

Grant Hill Orlando Magic contract

 

[78AlwaysHappy]

Here’s an early candidate: Wayne Garland, 1977 Cleveland Indians. First 10-year contract in MLB history. Twenty game winner with Baltimore in 1976, then 13-19 in 1977. Next four years 15-29; then out of baseball.

 

[navery12]

Every year, I post about Bonilla's contract because every year (and thread like this) gets it wrong.

1) Every team has deferred deals just like this one. Ken Griffey Jr was the 4th highest paid Red last season (2023) and gets 3.6m a year.

2) That deal, at the time, used the saved cash to sign Mike Hampton, Derek Bell and Todd Zeile, who all helped the Mets to the National League pennant in 2000. That alone is worth it.

And when Mike Hampton walked in FA after his one year with the Mets, the comp pick they received was possibly the greatest position player in team history before his injuries David Wright

 

[Scottobot]

In all seriousness, Anthony Rendon got paid $245M/7yrs from the Angels in 2020. He has played 52, 58, 47, 43, and 57 games in the 5 seasons since.

Mike Trout got like $450M/12yrs and has played basically the same amount of games as Rendon.

Basically any big contract the Angels give out will be a contender for the worst of all time

Angels deserve their own sub thread on this. they gave Josh Hamilton 125 million and he did nothing for them. they gave a very old Puhols 240 million.

 

[McLovin]

Jacoby Ellsbury with the Yankees

This

 

[McLovin]

While I generally think the posters of the Boneyard often speak out of their butts when it comes to sports, myself included, this thread made me realize that any of us could be as successful, if not more successful, than pretty much any professional GM. And that’s pretty wild.

 

[Deepster]

Angels deserve their own sub thread on this. they gave Josh Hamilton 125 million and he did nothing for them. they gave a very old Puhols 240 million.

Absolutely. Plus they have Mike Trout, supposedly our generational Mickey Mantle, who's done absolutely nothing for them.

 

[superjohn]

Absolutely. Plus they have Mike Trout, supposedly our generational Mickey Mantle, who's done absolutely nothing for them.

3× MVP with them, 11× all-star, 9× silver slugger.

Not much he can do about the rest of the team sucking and himself always getting injured.

It's wild they've had Trout, Pujols, Ohtani, and Hamilton and the team has always blown. That's easily four of the ten most talented players of the past twenty years.

 

[EBonz30]

3× MVP with them, 11× all-star, 9× silver slugger.

Not much he can do about the rest of the team sucking and himself always getting injured.

It's wild they've had Trout, Pujols, Ohtani, and Hamilton and the team has always blown. That's easily four of the ten most talented players of the past twenty years.

Just shows you baseball is nothing like the NBA or playing the QB position in the NFL- one or even two great players don’t guarantee any type of consistent success.

 

[FlippinCrazy!]

The blame lies with John Henry and FSG. They would have had 2 years of luxury tax penalties but would have come out the other side after Price’s contract expired. They’re cheap. That’s the bottom line. There’s no excuse to not spend on a frontline starting pitcher this off-season and the fan base is definitely paying attention.

Yeah clearly trying to save money to subsidize their other investments. But the Sox did spend frontline money on a starter. It just so happens they spent it on giolito and Hendricks, a starter with a 4.90 era the past 2 years (who ultimately bailed Breslow out of the embarrassment he would’ve been by getting hurt) and a reliever who we knew wouldn’t pitch this year and is coming off both Tommy John and cancer.

Breslow is one of the worst GMs/BPOs in baseball. Believe it or not, he simultaneously subtracted from the MLB roster and farm system, while adding on payroll. Between all his additions, he has something like a -3 WAR (despite trading a dozen prospects at the trade deadline) and that’s not counting who he’s traded away. For comparison, Verdugo has a 0.9 WAR and sale has a 5.8 WAR. If the sox kept Bloom, they’d be contenders in the AL East or at the very least, firmly in a wild card spot.

 

[UConnJim]

That is around the range the Sox reportedly offered before being traded. Again I do think he wanted to go to free agency to help the players and that it probably would’ve taken $35M-40M a year for 8+ years for him to sign an extension before Covid. In the end, the David price and Chris sale deals made offering that much almost impossible. They’d be committing ~$90M to those 3 players coming off a disappointing year they weren’t really close to making the playoffs, with very little talent in the farm system. Kind of similar to the Yankees last year, except without one of the top farm systems to go out and make a Juan Soto like trade or even just supplement at trade deadlines. In retrospect, yes mookie still would’ve been worth that, but I don’t blame the Sox for moving him.

I think Bloom should’ve taken on some salary dumps in those years after trading Mookie (look for one of those Carl Crawford / Adrian Gonzalez type trades that the dodgers/sox also made except be on the other end of it), or ate the Price contract to get some better prospects in the trade. But clearly Red Sox ownership wanted to cut payroll so that wasn’t happening.

The Red Sox weren't willing to give Betts a LT contract (12 years) so he didn't sign with the Red Sox and got traded to the Dodgers who gave him a 12 year deal.

 

[TheHorde]

Yeah clearly trying to save money to subsidize their other investments. But the Sox did spend frontline money on a starter. It just so happens they spent it on giolito and Hendricks, a starter with a 4.90 era the past 2 years (who ultimately bailed Breslow out of the embarrassment he would’ve been by getting hurt) and a reliever who we knew wouldn’t pitch this year and is coming off both Tommy John and cancer.

Breslow is one of the worst GMs/BPOs in baseball. Believe it or not, he simultaneously subtracted from the MLB roster and farm system, while adding on payroll. Between all his additions, he has something like a -3 WAR (despite trading a dozen prospects at the trade deadline) and that’s not counting who he’s traded away. For comparison, Verdugo has a 0.9 WAR and sale has a 5.8 WAR. If the sox kept Bloom, they’d be contenders in the AL East or at the very least, firmly in a wild card spot.

Agree with a fair amount of this but Giolito was not paid like a frontline starter. He was paid more like a #3. If the Red Sox sign Corbin Burnes, I’ll be impressed.

 

[millertime7774]

Aaron Hernandez. People within the Patriots organization knew he was a psychopath who had lifetime criminals as his assistants and some teammates steered clear of him. It turns out he already murdered two guys a month before the Patriots gave him a 5 year contract extension and gave him the highest signing bonus ever for a tight end.

At least they got out of the contract...

 

[TheHorde]

Aaron Hernandez. People within the Patriots organization knew he was a psychopath who had lifetime criminals as his assistants and some teammates steered clear of him. It turns out he already murdered two guys a month before the Patriots gave him a 5 year contract extension and gave him the highest signing bonus ever for a tight end.

I’m ashamed for not thinking of this one earlier.

 

[millertime7774]

I’m ashamed for not thinking of this one earlier.

 

[ahmed69]

Carl Crawford /thread

 

[SportsFan88]

WATSON by far cause the dude looks horrible especially for 230 M’s guaranteed, I also think of how Andrew Bynum fleeced my sixers in terms of bad contracts

 

[The Yakk]

3× MVP with them, 11× all-star, 9× silver slugger.

Not much he can do about the rest of the team sucking and himself always getting injured.

It's wild they've had Trout, Pujols, Ohtani, and Hamilton and the team has always blown. That's easily four of the ten most talented players of the past twenty years.

Sticking with old school dunderhead Mike Scioscia--Mr. Sacrifice Bunt--for 20 years while the rest of league made game decisions based on modern research certainly did not help.

 

[uconngb]

They paid him $100m/year for a two-year deal. He tore his ACL in his second game and has been out nearly a year at this point. By the time he gets back healthy — assuming it is only two more months — his deal will almost be over, and those two games will be all he’s played.

Nobody does it like Neymar. Even Trout’s got to be in awe of this.

Not sure you can blame a guy tearing his ACL as being a bad deal. Most of the examples offered up are guys who sucked and woefully underperformed their contracts without getting hurt. Other than giving a 160 pound power pitcher a 10 year $250 million contract when it was pretty obvious he was gonna blow himself up of course.

 

[uconngb]

At least they got out of the contract...

Excellent point

 

[Scoe]

Aaron Hicks is still paid through next year and 2026, great contract Cashman.

 

[Palatine]

Daniel Jones. Just giving this guy any contract bordered on the absurd.

 

[boog204]

Aaron Hicks is still paid through next year and 2026, great contract Cashman.

Have to be honest, I thought this was a good move at the time... Everyone knew Hicks had lots of physical talent and he was coming off back-to-back 800+ OPS seasons while hitting his prime. The deal was long, for sure, but cheap in the big scheme of things. It's one of those deals that could have been viewed as a great, great deal if Hicks had performed.

 

[Northbound]

The Broncos paying washed up Russell Wilson $64 Million and then letting him go to the Steelers while still having to pay him whatever the remainder is on that contract.

As a LONG time Bronco fan, like Craig Morton/Randy /Lyle Alzado long, I’m happy they have to pay that money because:

1) Gets rid of Russ
2) Causes the organization pain that I’m hopeful they learn from

 

[Excalibur]

Meatheaded simpleton Dave Gettleman's contract to run the NY Giants. He set the team back 8 years in his 4 years on the job.

More destructive than any player contract, ever.

It wasn't Gettleman (not that he was competent). It's the Mara family. Having dealt with them, they are very decent people who are in way over their heads at this point.

 

[The Yakk]

It wasn't Gettleman (not that he was competent). It's the Mara family. Having dealt with them, they are very decent people who are in way over their heads at this point.

We are probably both right.

I take your point about the Maras--since you dealt with them--but they could have hired someone better than Gettleman just by pure luck.

Was it the Maras who wanted Daniel Jones in the first round? Who flushed OBJ down the toilet because they didn't like his hair? Who hired the string of incompetent coaches?

Other successful teams have been able to overcome spectacularly dumb owners. Including the Giants themselves, when they had people like Parcells and Belichick and Coughlin running things.

It took exactly one Gettleman press conference for most Giants fans to realize we were doomed for a generation.

 

[alphasigko]

As a LONG time Bronco fan, like Craig Morton/Randy /Lyle Alzado long, I’m happy they have to pay that money because:

1) Gets rid of Russ
2) Causes the organization pain that I’m hopeful they learn from

What have they learned since the passing of Pat Bowlen? I submit: not much...