10. Chan Ho Park, Texas Rangers (5 years, $65 million)
The Rangers have never been known for their front-office savvy, but inking a fly-ball pitcher to a monster-money deal that requires him to pitch half his games in baseball's most dinger-friendly park was the textbook definition of self-sabotage. Predictably, Park got mauled and injured in short order. Here's a chicken-or-the-egg question for you: Is Park the Asian Carl Pavano, or is Pavano the dumbhead-American Chan Ho Park?

 

9. Roger Clemens, New York Yankees (4 months, roughly $18.5 million)
The only reason this one doesn't rank any higher is the possibility, however slim, that Roger can sustain his late-career resurgence for another few months. Hey, weirder things have happened (see under "Super Bowl, Peyton Manning's clutch performance therein"). Forget the numbers he put up in the dainty NL Central and his I-totally-do-push-ups-and-wind-sprints-every-day blather. You're looking at a guy who turns 45 in August, who has a recent history of groin pulls, and who rarely pitches into the seventh inning anymore. That's our Yankees, once again partying like it's 1989.

 

8. Alexei Yashin, New York Islanders (10 years, $87.5 million)
Even after the post-lockout NHL collective bargaining agreement sliced Yashin's deal by around 25 percent, it remains the sport's worst. The only other contender for that honor? Yashin's Islander teammate Rick DiPietro, inked to a 15-year (!), $67.5 million (!!!) deal before the 2006–2007 season. At least DiPietro appears to try, though. Yashin's stats in the Isles' four-games-to-one obliteration at the hands of the Sabres last month: no goals, no assists, no penalty minutes. He's Casper with a stick and a crash helmet.

 

7. Steve Spurrier, Washington Redskins (5 years, $25 million)
Upon arriving in the NFL after reestablishing the Florida Gators as an NCAA powerhouse, Spurrier mocked the habits of workaholic coaches like Jon Gruden ("Gruden can burn the midnight oil all he wants. Me, I don't leave the house a minute before Regis and Kelly bid their farewells. Yeee-haw!"). The good ol' ball coach promptly lazed his way to a 12–20 record over two seasons and resigned shortly thereafter, slinking his way back to the college ranks. How his monstrous ego survived the experience intact, we'll never know.

6. Bryant "Big Country" Reeves, Vancouver Grizzlies (6 years, $65 million)
At $2.99 for a Wendy's double with cheese, Reeves' eye-poppingly absurd contract gave him the means to procure…uh, a lot of double cheeseburgers. And yet the Grizzlies still expressed utter shock and dismay when he showed up at training camp looking as if he was in his third trimester. Sometimes, people are exactly what they appear to be: Reeves was out of the league within three years.