What are the worst contracts in sports history?

Early in the baseball season, two players are quickly emerging as ludicrously disastrous free agents signings. Barry Zito, who actually was signed last year, was inked to an enormous deal worth about $130 million, had a mediocre 2007, and so far in 2008 appears to be very close to the end of his career.

Meanwhile, in Detroit, Miguel Cabrera was handed a deal worth, IIRC, $153 million, and according to firsthand accounts has lost interest in trying, although he’s not actually all that bad yet.

What are sports’ most legendarily bad contracts - in terms of money wasted and disastrous on-field performances?

Let’s consider two categories:

  1. The **Surprise Bomb ** category, where a contract was astoundingly bad but you could at least understand why the team tried it. Cabrera is just 25 and was one of baseball’s finest hitters; I would have given him a big deal too.

  2. The **No Shit, Sherlock ** category, where a contract is a disaster and you saw it coming a billion miles away. The perfect baseball example is Darren Dreifort, a pitcher who was given an amazing $55 million deal despite being a pitcher of modest ability and accomplishment, and pitched badly, and very briefly, before hanging up his spikes to count his money.

What are the worst signings in football, basketball, hockey? Do you think there are worse ones in baseball? All sports welcome!

Isaiah signed a few of them. Do you want to count Kevin Garnett as the last max contract as hamstringing the Timberwolves so they had a really hard time getting talent around him?

The Rangers had a really nasty one a couple years ago. Alexander Yashin was up there, as well.

Kevin Brown, Darren Dreifort, Chan Ho Park, Denny Neagle, Mike Hampton, Carl Pavano, maybe Jason Giambi? What about Lary Brown? Allan Houston! (that was the Isiah one I was thinking about)

Eric Gagne’s Brewers contract.

How about Michael Andretti’s Formula One “season”? I’m guessing he made an awful lot of money off his last name for a few races of crashing often and early.

Two words: Ryan Leaf.

He was just following Mario’s example.
[Announcer] The cars are coming around at the end of lap 1 and Mario is pulling into the pits.[/announcer]

Football:

Tomas Brolin - Leeds United (Good once, but a little on the rotund side when he joined)

Ali Dia - Southampton (Graham Souness completely conned)

I think you can put Mike Vick’s 10 year, $130 million extension with the Falcons in this category. The contract was a stretch - Vick was never going to be the best QB out there - but he did add a unique threat to the Falcons offense. You might have expect ed him to miss time due to injuries or to hold out again at some point in the future, but two years in prison for dogfighting?

Eh, this is a different category. There’s nothing wrong with that contract so long as there’s no reasonable way that Arthur Blank could have known about the legal troubles. Vick would have been worth every penny of that money in team revenues had he played even half of it’s life and it would have been a bargain if he actually found a way to win a Super Bowl.

Unforeseen legal troubles and freak injuries aren’t “bad” contracts, just unlucky ones.

I think it’s tough to top that Barry Zito contract. The day it was signed just about everyone was laughing at the Giants. Popular opinion was that he was a pretty pedestrian pitcher at that point and there wasn’t really anyone bidding against them for his services. To set a record for a contract to a pitcher for a guy as mediocre as that is dumbfounding.

Also, the Ryan Leaf deal isn’t a bad one either. There was almost no reason to think he’d bust the way he did and really he didn’t get paid that much since it was a rookie contract that wasn’t guaranteed.

How do we classify the entire Knicks roster? Quentin Richardson, Jerome James, Stephon Marbury, and Steve Francis each have an embarrassingly awful contract, contracts which all were obviously horrible deals the minute they were inked. But when you consider that they all play the same position on the same terrible team just exponentially raises the level of atrociousness.

A-Rod.

The absolute insanity of his Rangers deal. Of course, he hasn’t been a flop as a player. But, if you’re going to pay that kind of money, you want World Series wins.

The Yankees gave Jim Spencer a contract guaranteeing that he would start against right handed pitchers. He didn’t do crap after that. Then there was Don Gullett, world class pitcher for the Reds, world class flop for the Yankees.

The Tigers gave Juan Gonzalez the sun, the moon, and all the stars to come play for them, even moving in the left field fence for him. His thanks was to play like a stiff and take a hike as soon as he could.

That’s on Texas, though, not on Rodriguez’s performance. They outbid themselves to get him and then didn’t spend much money on anything else. They still apparently don’t know how to choose pitchers.

Carl Pavano and Albert Belle both have to fit in there somewhere - long-term guaranteed contracts for spending years at a stretch on the DL.

I dunno. I agree that the salary comes with some hopes or even expectations of championship(s). But he’s been approximately the best player in baseball since then. I just can’t call it a bad deal. What can A-Rod do more than play at his best? I will grant you, he’s no Jeter in the clutch, though…

Joe

It’s very hard to beat Zito on the “should have seen it coming” list. The Cards extension for Mark Mulder (who most likely won’t pitch in the bigs again) was pretty obviously a mistake as well. Billy Beane sure knows when to cut bait with his pitchers.

In American football it’s much harder to make these kind of mistakes because so little of the money is guaranteed. Sure, you lose the signing bonus money, but you can always cut the player. That’s why these contract announcements are so ludicrous (10 years, $100 million) since so little of that money will ever be paid.

Basketball is rife with bad contracts, mainly because of the small rosters and salary cap. Teams have plenty of money so they just through it away. Isiah was the worst about this, but there are plenty of offenders.

Finally, I would disagree that A-Rod’s contract was a mistake. I think that, compared to what other players made over the time period, he has been pretty fairly compensated for his production and the amount of revenue he has raised for his team(s). The Rangers just blew the opportunity to put a real team around the best player in the game.

I think Allan Houston’s contract ( 6 yrs $100 million) from the Knicks merits special mention due to the fact that it was a good amount more than anyone else was offering, and he was known to have knee problems. Granted, the knee did hold up for a while, and Houston was a nice player when healthy, but the ending was fairly easy to spot coming.

Best of all though, the “Allan Houston Rule”, a new clause in the NBA’s CBA agreement where a team could clear a player’s salary and not have it count against the luxury tax, was not used for Houston. As a result, the Knicks ending up paying him $20M a year for 2 years after he retired.

::puts head on the desk and weeps quietly::

I love it how the league tried t bail the Knicks out with the “Allan Houston Rule”, yet the Knicks, under Isaiah, didn’t even exercise that rule. He should have been fired then.

Hence the category “Surprise Bomb.”

However, aren’t NFL contracts non-guaranteed? The Falcons aren’t out all that money, I don’t believe.

Nope, by far the worst contract ever was the Cubs signing of Andre Dawson.

A bit of background. Dawson was an offensive force to be reckoned with while playing for montreal, but playing on artificial turf was tearing up his knees. A free agent, he received no offers from any team. Wanting desperately to play on natural grass (and probably to get out of Montreal, as well) Dawson signed a blank contract with the Cubs and told them to fill in the amount. The Cubs gave him a one-year $500,000 (some reports say $650,000) contract and Dawson responded with a career year.

Dawson’s below-market-value contract from the Cubs was Exhibit A in the Players’ Association lawsuit charging MLB owners with collusion to hold down free agent salaries. (The Yankees’ withdrawl of an offer to Carlton Fisk was Exhibit B.) The owners eventually paid $280 million in damages to the Players’ Association