This was supposed to be easy. Well, relatively easy, as far as negotiations with elite free agents go. Jon Lester had the Red Sox, Cubs, and Giants to consider. The Red Sox were the team that drafted and developed him, and Boston is where he put in all the work that made him famous. The Cubs had his former general manager and other old friends in charge, and presented a new challenge as a franchise that hadn't won a World Series since before Jon Lester's grandparents were (probably) born. The Giants have his good friend Tim Hudson under contract, and have won three World Series in a five years in front of a devoted, loving fan base. All three had the money to pay him, so it was just a matter of figuring out which destination fit Jon Lester best, and the idea was to decide this week, before the winter meetings.
Then the Dodgers came along, dropping their mystery team disguise in the course of about 24 hours. They have their own former Red Sox officials, their own former Lester teammates to trot out, and more money than maybe any team in sports. Yes, maybe even more than the Yankees. With all four of these teams looking as if they're varying degrees of all-in on Lester, his decision has been delayed according to FOX Sports' Ken Rosenthal, and will no longer come before next week's winter meetings begin.
On the one hand, this isn't bad news, as it gives the Red Sox a little more time to formulate some backup plans while the market is frozen, waiting for Lester to sign. On the other hand, please end this torture and make a decision so we all know who is going to lead the Red Sox rotation in 2015 sooner than later whether it's you or whoever the Red Sox decide is to be entrusted with taking over your rightful place. Please?
With the Dodgers' involved, it sounds more and more as if it's going to take $150 million to sign Lester, as they can get him that $25 million average annual value he wants. They can sign Lester outright under the expectation that Zack Greinke is going to be gone in a year when he opts out. They can trade Greinke in advance of that to clear payroll and fill another hole with the return, safe in the knowledge that Lester will be there in place of him for the next six years. They can trade Matt Kemp -- and are in discussions with the Padres and others to do so at this very moment -- to clear up their outfield logjam and most of the budget space for a hefty new Lester deal. The Dodgers have options, and their inclusion in negotiations has made things more difficult for everyone involved. In Jon Lester's case, difficult is not necessarily a negative thing, however: dude has his own options, and they are all going to make him a rich man. He just has to decide which will make him happiest, and what remains in this week apparently was not enough to figure it out.