Each offseason, there are a few contracts signed by free agents (or soon-to-be free agents) that make headlines because they are for astronomical amounts of money. Since this has been a relatively new phenomenon in baseball, just in the last few years have we been able to look back at the life of the contracts and just see how few of them actually work out.

Sometimes they do and even become bargains (Pedro Martinez’s Red Sox contract). Sometimes, the team ends up not being able to afford it and have to trade the guy and pay some of the money even though he is still good (A-Rod). Other times, the contract becomes laughably horrible. This is especially true of pitchers.

This week’s Top 7 looks at the worst contracts ever signed in baseball.

7. Barry Zito

After the 2006 season, Zito signed a 7-year, $126 million contract with the Giants despite all indications that he was on the decline. In his second season, it is already at a point where the Giants would have to eat a decent portion of the money in order to get rid of him. Actually, that may have been the case two seconds after he signed it, kind of like the old adage that a new car loses its value as soon as you drive it off the lot. Zito is now 0-4 on the season and an above-league average ERA last season in one of the best pitching parks in baseball. Since he has no history of injuries, it could be tough for him to move higher up this list, but this contract is headed nowhere good.

6. Scott Rolen

Plenty of players could have occupied this particular spot, but Rolen seems like the best fit, especially since the other two—JD Drew and Juan Pierre—are both Dodgers, and their fans have been tortured enough with the rest of this list. Rolen signed a $90 million contract with the Cardinals in 2003 that paid him through 2010, and it seemed like can’t miss, especially when Rolen tore up the 2004 season. Since then, he has barely been able to stay in the lineup, had continuous spars with Tony LaRussa, and has been traded to Toronto, where he started the season on the DL.

5. Jose Offerman

His contract was sort of a breakout where teams were finally allowed to overpay for suspect players. While his four-year, $26 million Red Sox contract sounds more like a deal you give to a 46-year old reliever nowadays, it sure seemed like a ton to give a horrible defensive second baseman with not-exactly Jeff Kent offensive ability. The Sox ended up trading him before the deal ended, and the door was opened for atrocious contracts everywhere.

4. Jason Schmidt

You have to feel for Dodger fans when during the second year of a $45 million contract, their guy has only pitched 25.7 innings with a 6.31 ERA, and it’s not even close to the worst pitching contract that the team has handed out. You could have thrown the Kevin Brown contract on this list easily too.

3. Mike Hampton

While the Rockies were still trying to find out how in the world to win at home, they signed Hampton to an 8-year, $121 million contract after he had an unbelievable 2000 playoffs. He only lasted two seasons in Colorado before they could no longer afford him and he ended up in Atlanta. The best part about Hampton’s contract now is that there are 3 teams still paying him (inexplicably, including the Marlins), and that he is still getting paid even though he hasn’t pitched since 2005.

2. Carl Pavano

The Yankees gave him four years and $40 million before the 2005 season. Last year, he pitched in two games. The year before, he did not pitch at all. In the contract’s first year, he pitched crappily in 17 games. He is due back at the All-Star break of this season. If he goes 14-0 with a 1.11 ERA, he may be able to get off of the list.

1. Darren Dreifort

Anyone who checks out the ingenious Dodger Blues website laughs about this contract at least once a week. The Dodgers signed Dreifort before the 2001 season for five years and $55 million. When the contract was finished, they ended up paying him $275,000 per inning (200 innings), or $6.1 million per win (9 wins). He only pitched in three of the seasons, never throwing more than 94 innings or getting more than four wins. But he did get a save in 2004! They didn’t even sign him as a reliever either!

The Top 7 is written by Jason Major. His JSF contract pays him in cyber hand-pounds. Email him at jason@joesportsfan.com