Worst Contracts In Pro Sports History

[TheHorde]

Dak Prescott

While I would definitely agree that he’s not worth that money, I think it also signifies how weak the incoming crop of QB draft prospects is, and how hungry the QB needy teams are to get a QB. Sadly, if the Cowboys didn’t give Dak that deal, the Raiders or Cowboys might have next offseason.

 

[FlippinCrazy!]

I would have offered $31-32 million per year for 10 years early and if he turned it down, so be it. On a WAR basis, I thought he was worth that. They would have struggled with the luxury tax for a couple of years, but then would have come out the other side just fine.

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.

 

[uconngb]

While I would definitely agree that he’s not worth that money, I think it also signifies how weak the incoming crop of QB draft prospects is, and how hungry the QB needy teams are to get a QB. Sadly, if the Cowboys didn’t give Dak that deal, the Raiders or Cowboys might have next offseason.

Right place, right time for him no doubt......but he's not worth haff that money, and I mean that on a relative basis. Obviously all of these contracts are just insane.

 

[Inyatkin]

Some weird entries on this list. A lot of injuries for Trout or Kawhi but anyone would have taken them and paid that at that point in their careers.
Giving big money to Daniel Jones, ever? That's a different story

 

[Tenspro2002]

I always think of this guy when this topic comes up... Rusney Castillo - Wikipedia

On August 23, 2014, the Boston Red Sox signed Castillo to a seven-year, $72.5 million contract. Castillo was given the jersey number, 38, which he wore in Cuba.
Overall, in parts of three seasons with Boston (2014–2016), Castillo appeared in 99 MLB games, batting .262 with 7 home runs and 35 RBIs.

When I lived in Boston I went to one of his first games in 2014 and saw him hit a home run, in fact it may have been his first.

 

[AZHuskiePop]

The PAC 12
paying anything to .
to Commissioner George Kliavkoff
as he presided over the destruction of a 100+ year old institution.
i think hr is still getting paid.

 

[RJScootin]

Carl Pavano got paid $40M for 9 wins with Yanks, played in 26 games and averaged $250K per inning pitched over his 4 years contract.

 

[superjohn]

Some weird entries on this list. A lot of injuries for Trout or Kawhi but anyone would have taken them and paid that at that point in their careers.
Giving big money to Daniel Jones, ever? That's a different story

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

 

[Matrim55]

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.

 

[superjohn]

Carl Pavano got paid $40M for 9 wins with Yanks, played in 26 games and averaged $250K per inning pitched over his 4 years contract.

Yeah but the Yankees paid Kevin Brown over $15 million per year for his two brilliant seasons pitching for them so it balances out.

 

[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.