Discussion: The Worst Signing Of The Offseason

Look no further than the Toronto Blue Jays or the Chicago Cubs to see the kind of franchise-changing effect a bad contract can have on an organization. Alfonso Soriano and Vernon Wells both signed nine-figure deals that their clubs must be regretting. Though the free agent market was depressed last winter, we saw teams commit to some massive deals.

There doesn't appear to be a Barry Zito–esque clunker among them, but some teams still overspent. Now that the regular season is only ten days away from completion, we have nearly an entire season's worth of information to help decide which move was the worst. (We won't really know how good or bad these deals are until they expire, of course, so we'll simply use the information we have so far.)

If you check out MLBTR's list of last winter's 20 biggest moves, you'll find that last offseason's most lucrative deals appear to have worked out. Where would the Yankees be without Mark Teixeira, C.C. Sabathia and A.J. Burnett? Ryan Dempster pitched well for the Cubs and Derek Lowe and Manny Ramirez added value to their respective clubs. But not every signing looks good. Here are some candidates for last winter's worst free agent signing:

• Oliver Perez - $36MM over three years - He allowed 51 runs in 66 innings for an ugly 6.82 ERA. Knee injuries shortened his season, but he still managed to walk 58 batters, almost one per frame.
• Milton Bradley - $30MM over three years - The volatile outfielder saw his OPS tumble by over 200 points this year. His off-field antics led to a suspension and the Cubs will now try to find a taker for the 31-year-old.
• Edgar Renteria - $18.5MM over two years, plus club option - Those who criticized the Giants for this deal appear to have been justified. Renteria hit just .250/.307/.328 and didn't play good enough defense to make up for his struggles at the plate.
• Jamie Moyer - $16MM over two years - To his credit, Moyer pitched over 150 innings for the defending champs. Still, do the Phils want to pay a hittable 47-year-old $8MM next year? Probably not.
• Pat Burrell – $16MM over two years – It's one thing for the Phillies to mis-spend, but the Rays don't have money to throw around. Andrew Friedman envisioned more than a .382 slugging percentage when he signed Burrell last winter.

So which of these contracts is the worst one? Was $161MM too much for a pitcher? Will Derek Lowe wear down? Let's hear your thoughts in the comments section.