The upcoming free agent class has its share of big names, including Cliff Lee and Carl Crawford. Lee's free agency was delayed by one year because of the extension he signed with the Indians four years ago. Crawford's chance at a huge payday was pushed back two years because of a deal he signed with the Rays more than five years ago. Imagine if all players took the riskier but more potentially lucrative approach, forsaking multiyear extensions. These players would be hitting the market:
- Catchers: Yadier Molina, Chris Snyder. Molina lost money by choosing the security of a long-term deal, though Snyder was smart to sign one.
- First basemen: Kevin Youkilis, Justin Morneau. I doubt they have regrets about signing, but both players would be primed for huge free agent contracts this winter. Then again Morneau hasn't played since July 7th due to a concussion and Youkilis' season ended on August 2nd with a thumb injury. Maybe teams would have been cautious of major commitments.
- Second basemen: Brandon Phillips. He would've scored big on the open market; there's not much at this position and he's only 29.
- Shortstops: Maicer Izturis, Ramon Santiago.
- Third basemen: David Wright. Wright's had his ups and downs this year but as a 28-year-old he would have done well.
- Outfielders: Grady Sizemore, David DeJesus, Jason Kubel, Alex Rios, Nick Swisher. DeJesus and Kubel have club options that will probably be exercised. Sizemore's contract was once considered a massive bargain, but now his 2012 option is in question. Rios and Swisher would be entering free agency off strong seasons.
- Starting pitchers: Zack Greinke, Dan Haren, Scott Kazmir, Joe Blanton. Greinke might be wishing he didn't have another two years on his contract, while Haren could probably beat the two years and $29MM he has remaining. Kazmir and Blanton, though, are likely glad they have security.
- Relievers: Huston Street, Matt Thornton. Contrasting would-be contract years. Street didn't debut until June 23rd this year due to a shoulder injury. Thornton continues to dominate, making his 2011 club option an easy decision.