The Darren Dreifort divison
For players with injury histories signed to monster deals that everyone knows will not end well.

Gil Meche signs a 5-year $55 million contract with the Royals
    His 55-44 record and 4.65 don’t seem all that bad on the surface, but when you realize that Meche made his debut in 1999, missed all of the 2001 and 2002 seasons with arm trouble, has never posted more than 15 wins and has only started more than 30 games and surpassed 150 innings twice in the seven seasons in which he has pitched, things start to look a little less rosy. The Royals stink, and I understand the need for them to shell out some money in order to debunk the myth (which happens to be entirely true) that they pocket all of the revenue sharing money they receive. Still, five years and $55 million for Meche doesn’t get them any closer to respectability, even though he’s the only coveted free agent that new GM Dayton Moore could snag. It’s sad for a long-time baseball city like KC, but it’s going to be even sadder when Meche starts out 10-2, makes the All-Star team, then blows out his arm in July and doesn’t pitch again until 2009.

J.D. Drew signs a 5-year $70 million contract with the Red Sox
    Everybody (and I mean everybody) in Boston knows that this is going to end badly. Even if the Sox reduce the guaranteed money and increase the incentives because of the concern over Drew’s shoulder that has held up the finalization of this deal, it’s going to end badly. At his best Drew is a talented athlete that can do pretty much anything on a baseball field. At his worst he’s an injury-prone prima donna that is just as likely to miss two months with a hangnail as he is to drive in 100 runs (which he has done once, driving in exactly 100 last season). It’s been reported ad nauseum, but replacing fan favorite and gamer Trot Nixon with Drew is like replacing Jennifer Aniston with Angelina Jolie. Sure, Brad Pitt seems pretty pleased with himself now, but what happens when Angelina blows out a rotator cuff picking up her most recent adopted child from a third-world country?

The Derek Jeter/Albert Pujols division
For those rare contracts that make perfect sense in terms of length, dollars, and fulfilling a team’s need. (In Jeter’s case, being a Yankee icon before he turned 25 didn’t hurt either).

Jason Schmidt signs a 3-year $47 million contract with the Dodgers
    To be honest, I didn’t think GM Ned Colletti had it in him (especially after Drew took a hike and the Juan Pierre debacle of a contract), but he came through. Schmidt does have an injury history that might make this signing a gargantuan waste of money, but if he stays relatively healthy this signing might be the best of the offseason. Schmidt was one of the top five starters available, arguably number two after Zito. And because he’s older (33) with some mileage on him (he’s pushing 2,000 career innings), the Dodgers were able to sign him for a relatively short-term commitment at a fair price. At a time when Gil Meche and Ted Lilly are getting more than $40 million in guaranteed money, an older star with some tread left on the tires like Schmidt is practically a bargain for less than 16 million per.