Nomar Garciaparra had a similar situation with the Red Sox in 2004. Nomar was making a superstar's salary of $11.5 million that year and during the season the Sox offered a $60 million, four-year extension. Nomar said no, figuring he could get more on the free-agent market. That forced the Sox' hand. Knowing he wouldn't likely leave, they traded him to the Cubs midway through the season. Then he got hurt. He was hurt again in 2005 and landed with the Dodgers last season. After a good comeback year Nomar signed a two-year, $18.5 million deal to remain in L.A. Not bad, but still short of that $60 million package he turned down with the Sox.
So the smart thing is to re-up when your team offers you a fair-market deal. That's what Vernon Wells did. It's an old story. A bird in the hand... You know the rest.

Nomar screwed up big time by rejecting the Sox deferred $48 million deal, but he still gutted it out and wound up with around $40 million from 1 and 2 year deals. As for the Sox, they obviously made one of their best moves here, dealing Nomar for a World Series Championship. The Lesson? Sign the players that you would like to keep at least 1 year before free agency, and deal the ones that you don't plan on resigning. With an average 9% salary increase over the last few seasons, waiting is extremely costly. Exhibit A is Iron Man Johnny Damon, who signed for what the Sox thought was an outrageous $52 million over 4 years with the Yankees. Fast forward to 2006, and the Sox are now forced to give a talented but brittle(He has only played over 140 games once in 8 full big league seasons) J.D. Drew $70 over 5 years to fill a hole that was essentially created by Damon's departure.

Exhibit B is Pedro Martinez, who would have signed for Schilling money (3 years and $33 million) before the 2004 season. Sure they would have lost the 2006 season, paying him $11 million to sit on the D.L.. Instead, they ended up paying Matt Clement $9 million last season to sit on the D.L., and another $10 million this season to rehab for a 2008 season with another club. The most important point is that Pedro was healthy in 2005. Adding Pedro to the 2005 rotation would have given the Sox a great shot at back to back World Series titles. A little hindsight? Maybe, but the sign 'em or deal 'em formula pans out much more often than not. Just try it. The Red Sox seem to finally be getting this, as they signed Crisp and Beckett to deals that are now below market value. Nice job Theo.