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.
5. Michael Vick, Atlanta Falcons (10 years, $130 million, including a $37 million signing bonus)
Say all you want about the Falcons' dysfunctional offensive philosophy, their failure to provide even C-list receiving targets, and their inability to decide whether he's a pocket passer (nuh-uh) or a running one (as anybody who's ever seen him play might attest). The bottom line is that for $37 million upfront, you'd like your franchise QB to be able to put the ball within eight feet of the receiver's hands on a simple post pattern. You'd also like him to refrain from allegedly turning one of his homes into the dogfighting equivalent of Madison Square Garden.
4. David Beckham, Los Angeles Galaxy (5 years, $250 million, which includes endorsements)
At 32, Beckham's best days are behind him, plus most American sports fans won't give a hoot about soccer unless the game perks itself up considerably (maybe they could add a second ball? seek jail time for divers?). He can yammer all he wants about becoming the soccer Jesus who awakens kids to the sport's glories, but the Galaxy ain't paying him to teach little Billy proper corner-kick technique. Unless he single-handedly gets MLS to register on the public consciousness, his deal will go down in history with Glitter and the Whitewater investigation.
3. Allan Houston, New York Knicks (6 years, $100 million)
The genius of the New York Knicks during the Scott Layden and Isiah Thomas eras has been the team's almost uncanny ability to misread every market and personnel dynamic. The Houston signing ranks as perhaps the most damning example, as the Knicks not only threw roughly $40 million more at him than any other suitor was prepared to offer, but they did so knowing that he had cellophane knees. Even when the NBA offered relief via what quickly became known as "the Allan Houston rule" (which allowed a team to take its worst contract off the books), the Knicks didn't even take advantage of it. To repeat: the Knicks didn't use its Allan Houston rule exemption on Allan Houston.
2. Larry Brown, New York Knicks (5 years, $50 million)
For $10 million and a commissioner-negotiated $18.5 million buyout after a single season, the Knicks got 23 wins and 3,237 tabloid headaches out of their brief acquaintance with the nomadic Mr. Brown. Yup.
1. Mike Hampton, Colorado Rockies (8 years, $121 million)
When Hampton left the Mets to sign with the Rockies, he cited the high quality of the Colorado public schools as a prime reason. Here's hoping his kids learned their timetables as Hampton bounced from Colorado to Florida to Atlanta, forgetting how to miss bats and losing two full seasons to injuries along the way. Even after ditching him and his 6.15 ERA after the 2002 season, the Rockies are still on the hook for his $6 million buyout in 2009…unless the Braves decide to pick up their $20 million option for that season, which ranks between a month-long solar eclipse and Subway's Jared winning a Grammy on the scale of remote possibility. Basically, Hampton's contract is to baseball what herpes is to circa-1987 barflies.