Worst Contracts In Pro Sports History | Page 2 | The Boneyard

Worst Contracts In Pro Sports History

FlippinCrazy! said:
They supposedly offered Mookie $300M but Mookie wanted to go to free agency to help the players. Mookie later said they didn’t offer him that. I tend to side with the Sox at least offering in that $300M range, and Mookie only signing the extension with the dodgers after Covid hit and there was a lot of uncertainty about what the upcoming free agents would get that offseason. No proof, that’s just what I suspect.

They did save a lot of money on David prices contract, about 50% of the remaining contract was included in that mookie trade. The trade was at least better than the sale trade…
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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.
 
alphasigko said:
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.
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Plus all the draft picks
 
I'm gonna go with JaMarcus Russell. He hadn't proven a single thing when he got his $68 mill contract with $32 mill of that guaranteed. Lasted 2.5 seasons, all of it mediocre or worse.
 
Spaceman213J said:
Carl Crawford's was pretty bad in Boston. Jason Werth did practically nothing for the Nats. I saw him a few times rehabbing at A ball when he was there.
For me, as a Sox fan, I still have to go with David Price. I know he had a decent World Series the one year, but it was a big contract given to a guy with a lot of innings on his arm and many believe helped make ownership hesitant to give out long large contracts after that and may have helped the Sox to decide to low ball Mookie Betts and send him to the other coast.
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Sale’s extension was wayyyyy worse than price. The guy turned into balsa wood. Before they shipped him out this year of course. Price had far more to do with that WS win than Sale and they were at least able to dump him sooner.
 
FlippinCrazy! said:
They supposedly offered Mookie $300M but Mookie wanted to go to free agency to help the players. Mookie later said they didn’t offer him that. I tend to side with the Sox at least offering in that $300M range, and Mookie only signing the extension with the dodgers after Covid hit and there was a lot of uncertainty about what the upcoming free agents would get that offseason. No proof, that’s just what I suspect.

They did save a lot of money on David prices contract, about 50% of the remaining contract was included in that mookie trade. The trade was at least better than the sale trade…
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Mookie was NEVER staying in Boston. Period
 
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Albert Haynesworth 7 years 100 mill with Washington

Allen Houston 6 years 100 mill with the Knicks
 
Scoe said:
Currently the Kwahi Leonard contract, does he ever play? In hindsight obviously the right deal.
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Some great ones on thus list, but Kwahi was one of the 1st to pop into my mind after the obvious ones.
 
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Also...

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Ilya Kovalchuk's 17yr $102MM with the devils. Set the organization back a decade...I think this year is the last year for cap hit and he retired from the NHL over a decade ago.

Crazy story if you read about it - $3MM fine (which was and still is a huge amount...more so for a not well funded NHL team) is the 2nd highest team fine ever behind the Astros when they cheated their way to a world series. The original contract got cancelled (then restructured), cost them multiple draft picks, and Kovalchuk only played 3 seasons before heading to the KHL. Kinda weird as a Devils fan cause I still really like Kovalchuk but it absolutely tanked the organization for a decade
 
Scoe said:
Some of these bad contracts I hate to say are UConn alums, the Ben Gordon and Charlie Villanueva Pistons contracts.
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They like paying UConn guys. Rip really worked out for them. I wouldn't say Ben, Charlie, and Andre worked out for them.
 
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WrenchFan69 said:
Dak Prescott
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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.
 
TheHorde said:
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.
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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.
 
TheHorde said:
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.
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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.
 
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
 
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millertime7774 said:
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.
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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.
 
Inyatkin said:
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
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Did you edit this and take Pujols name out? I was going to tell you why the Pujols contract was always a terrible one.
 


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