That’s not really in the spirit of the question, though. As Omniscient points out, then you get into trades, and “What are the worst trades in sports history” is really a question deserving of its own thread.
It’s interesting that you have defined these contracts as “bad”. For the athletes involved, they are the greatest things EVER.
The dollar amounts in these two cases don’t compare with some of the other examples cited, but the Red Sox’ free-agent signings of pitchers Matt Young and Danny Darwin in December 1990 were criticized at the time.
Boston paid Young $4.53 million over two years ($7.49 million in 2007 dollars), according to baseballreference.com, and for what? A won-lost record over both seasons of 3-11 with a 4.92 ERA, as I calculate it, or about $1.5 million per victory. And with a career W-L record of 51-78 before joining Boston, it’s not as though he had shown a lot of promise.
The Sox also paid Darwin $12 million over four seasons, which may seem like a lot for a total W-L record of 34-31 and 4.14 ERA - heck, it is a lot. However, I wasn’t pissed about that because I thought Darwin pitched better than his W-L records indicated for the most part, displaying his usual excellent control (about 2.5 K’s per walk) and giving up a home run only every 13 innings or so. Darwin’s career W-L record of 171-182 may not seem too impressive, but I think it’s pretty good considering he spent the biggest chunks of his career with the 1978-84 Texas Rangers and the 1986-90 Astros, which boasted precisely one postseason appearance between them. And his career ERA was superior to the league.
Just to update, today, reports are saying Jones has a bit of torn cartilage in his knee and surgery is a possibility.
Sort of stirkes me as coded language for “He sucks, we don’t really know why, but this gives everyone an easy out to drop him from the lineup, play someone better than AA level, and focus on the fact that Juan Pierre is an abomination at the plate.”
There, there.
We can put the Worst Contract trophy on the shelf next to the Worst Trade trophy (Orlando Cepeda for Ray Sedecki). They look good together.
How about the David Beckham deal to play soccer in LA. As far as I can tell it looked like he’s only played thirteen games for a whole lot of money.
Then again I have the soccer insight of a baseball fan, and the Californian insight of a New Englander.
He’s sold tickets and jerseys, raised the profile of the Galaxy, and raised the profile of MLS in general to previously unthinkable heights. Even if he never played a game he’d be worth the money, just as Pele was when he signed up to play here with little to nothing left in the tank.
I’ll admit that he raised buzz in the sport, but American interest? I don’t know any converted soccer fans from his arrival. As opposed to Sidney Crosby making hockey exciting again, or Lebron James putting a Cleveland basketball team on the map in the past 2-3 years. Lot’s of tickets and merch for those two as well.
I’m one. Not that I wasn’t a soccer fan before, but I couldn’t bring myself to watch MLS.
Now I watch 2-3 games a month, and if the Tampa Bay Mutiny hadn’t folded I’d probably have gone to a few.
That was the worst Giant trade? I would’ve thought George Foster for Frank Duffy or Gaylord Perry for Sam McDowell would’ve replaced it long ago.
Yeah, I thought of those after the edit window closed. Plus I couldn’t remember Frank Duffy’s name. 
Let’s call it a Triumvirate of Shame.
Actually, Ricky Williams had one of the worst contracts from a player perspective (how come these discussions always look at things from the management point of view?). Remember his agent was Master P, and most of the money was attached to ridiculous incentives that Williams couldn’t meet.