The Red Sox drafted Jon Lester in 2002. He’s spent his entire career with the club, overcome cancer with the club, and won two World Series rings with the club. His teammates refer to him as a role model, and he’s been a force at the top of the rotation for the Red Sox. After all his success with the club, however, it looks like he’s spending his final months in a Red Sox uniform.

This outcome certainly could have been avoided if the Red Sox had given Lester a competitive offer in Spring Training. Lester made it clear multiple times that he was willing to take a discounted deal to stay with the club. Instead, the Red Sox apparently offered a deal so far below market value that negotiations stalled.

Will the Red Sox really lose Jon Lester? Photo by Kelly O'Connor,

Will the Red Sox really lose Jon Lester? Photo by Kelly O’Connor,

The Red Sox have taken the logical, safe route here, avoiding a long term deal with a pitcher who’s on the wrong side of 30 and has already thrown over 1500 innings in the major leagues. This approach, though, has the team on the verge of losing their number one starter, a truly elite pitcher who will be extremely difficult to replace.

The Lester contract situation exists in a nexus where performance, physical concerns, the best interests of the team, public relations, and fan opinion all interconnect. Put in another way, it’s a situation where the head and the heart disagree. The cold facts are that pitchers can break down at any time, and signing older pitchers to long term deals rarely works (CC Sabathia and Johan Santana say hi). The heart responds that Lester is a Red Sox lifer, and that the Red Sox can’t afford to lose their ace.

The recent situation with Houston Astros and first overall draft pick Brady Aiken demonstrated how the head and heart can collide. The Astros eventually decided not to sign Aiken at top dollar, a logical move based on a problem found in his physical. This decision, however, led to a storm of negative fan and press reaction, and led to the Astros missing out on three of their best picks from the draft. By sticking to their guns and making a logical move, the Astros front office may have hurt the club overall.

In the past, the Red Sox have come down on the side of cold logic, jettisoning players at the back end of their careers rather than overpaying for declining numbers. The current ownership group allowed Pedro Martinez, Derek Lowe and Johnny Damon to leave after 2004/5, and recently didn’t make much effort to retain Jacoby Ellsbury.

There are examples, though, of bringing back players who take a bit of a discount to stay. Mike Lowell, David Ortiz and Mike Napoli all took offers that were less than what they could have got on the open market. Lester made public statements that he would consider a discount, but so far that hasn’t created any movement in the negotiations.

The Red Sox are taking a huge risk by not getting a contract done by the end of the season. They will have an exclusive window to negotiate with Lester, but with free agency that close he may opt to see what offers he can get on the open market. At that point it would be unlikely that the Red Sox would match whatever offers he gets.

The Red Sox did sign Dustin Pedroia to a long term deal last season. In that situation, the team and player managed to find a middle ground between what he could get in free agency and the amount of risk the club was willing to take. With Jon Lester, Red Sox fans hope in their hearts for a similar deal.