Lester Situation: Complicated and Frustrating

Jon Lester said in spring training that he really wanted to stay in Boston, but that he wanted a fair deal. His agent, Seth Levinson, also reps Pedroia, so the Sox aren’t dealing with Scott Boras here. So if the Sox had offered anything close to market value for Lester by now, he would be locked up. They haven’t, and Buster Olney wrote today that Lester’s close friend says there is “no chance” he signs with Boston at this point, reinforcing what history says about players resigning with teams after they trade them (they don’t). So Lester is gone forever by Thursday.

Paying Market value for 30 year old pitchers isn’t great business. It’s probably even bad. Even big money starters that signed with their own teams (Verlander, Sabathia, Cain) look like albatrosses going forward, so it’s not a case of not knowing a free agent inside and out. Verlander was way better than Lester ever was, and Fangraphs has his contract as the 2nd worst in baseball, even worse than A-Rod. Selling high on Lester at 30 isn’t a bad move, considering that he won’t have his binky David Ross forever, and that Jake “Washed” Peavy just got two prospects that at least are future relievers. Few teams are selling, and Lester is the best guy on the market, even if he is a rental. Another team could even ask for another of Boston’s expiring contracts (Andrew Miller would be a prime candidate) to sweeten the deal, a la the A’s and the Cubs. The Cubs got a top-10 prospect in the whole league for a pitcher worse than Lester (Jeff Samardija), even if he had another year of control, and another decent expiring player (Jason Hammel). Recent rentals have gotten very good return, and Lester is dealing right now.

If this was the Rays, or any other team that’s not the Yankees or the Dodgers, sending Lester and his World Series rings on his way would be right move. And the Red Sox have a budget, too, which is why the Dodgers trade was so important. Two things about that, though: a ton of money is coming off Boston’s books in the next two years — and why do the Red Sox have a budget??  The Red Sox only have $80 million committed for 2015 (just more than half of their 2014 payroll, when Cherington has said they want to be contending again), and $13 million for 2016. A lot of prospects are in the pipeline, which is why Cherington did those short term deals that are coming up in the next couple years. Young guys are cheap, so there is room for Lester, and more importantly, none of those prospects will be probably as good as Lester will be – even after 30. “Payroll flexibility” doesn’t start game one of the playoffs.

The bigger issue is that ownership has a payroll limit in the first place. That ain’t none of my business, but the Red Sox print money. NESN is the owners’ puppet, and WEEI is paying the Sox so much that they couldn’t afford to have the Celtics anymore. It costs $50 to park… and I could go on. John Henry even said in spring training that the luxury tax isn’t necessarily a hindrance going forward. So why is ownership not giving support to a Lester extension? So that John Henry feels good about having a bunch of undervalued players? Wins per dollar spent is something for Tampa to celebrate.

It’s awful that Lester’s going to leave. The Red Sox make so much money that they should never be sellers, and they should never let a stud go unless he is a Manny-in-08 level asshole. But I don’t own the Red Sox, so they will probably trade the first player drafted by John Henry. Boston should get a lot back though, so a trade won’t be that bad, because they will be selling high. Unless Matt Kemp is involved. Then it’s a disaster, but it sounds like he isn’t, Thank Bill Belichick (God).


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