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

Worst Contracts In Pro Sports History

FOX paying Brady $375M for 10 years as a commentator has to be up there...and I say that as a Pats fan. Just a remarkable waste of money. The NFL is a ratings monster no matter who is commentating in the booth. Adding Brady does absolutely nothing. They'd get a better ROI by giving that money to Taylor Swift to be in the booth every week lmao
Doesn't really count for this thread. The question is, "Watching the Browns vs Cowboys, it got me thinking about the worst contracts teams have given out."
 
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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.
 
Jason Werth did practically nothing for the Nats. I saw him a few times rehabbing at A ball when he was there.
Speaking of the Nats, what about Stephen Strasburg's contract? 7 years and $245 million and he made just eight starts and pitched 31⅓ innings after signing his free-agent contract. That's pretty bad.

Similarly Chris Sale's 5 year $145 million contract with the Red Sox was an absolute bust. Of course the Sox get rid of him for the last year of the contract and he's probably going to win the NL Cy Young. Smdh.
 
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…
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.
 
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.
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.
 
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…
Mookie was NEVER staying in Boston. Period
 
Albert Haynesworth 7 years 100 mill with Washington

Allen Houston 6 years 100 mill with the Knicks
 
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
 
Some of these bad contracts I hate to say are UConn alums, the Ben Gordon and Charlie Villanueva Pistons contracts.
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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