Off Season Winner: JD Drew

Way back in 2006, JD Drew made the controversial decision to opt out of his contract with the Los Angeles Dodgers in the hopes of landing a more lucrative contract on the free agent market. Drew was due to make $33 million over the next three years with the Dodgers, but thanks to an opt out clause in his contract, he was allowed to leave the Dodgers for the almighty dollar.

Not surprisingly, Drew, who was coming off a fantastic 2006 season with the Dodgers, landed a huge 5 year/$70 million dollar contract with the Boston Red Sox. Drew became the Red Sox' highest paid player and his decision to opt out of his contract netted him a cool $37 million dollars. Not too shabby.

So why did I put JD Drew in the "offseason winners" column this year? Well, because if JD Drew had not opted out of his contract with the Dodgers, then he would have been a free agent after this season. Considering how much Matt Holliday and Jason Bay are struggling to land big contracts on the open market this winter, there is little to no chance that Drew would have landed as lucrative a contract this winter no matter how good his production was.

In a sense, by taking himself off the 2009 free agent market, JD Drew avoided being a free agent in a weak market and maximized his earning potential more than he probably should have been able too.