The Red Sox' decision to trade Jon Lester has been made quite a bit easier, says Jayson Stark, by the ideal market that's developed for the starting pitcher.
With so many top free agent starting pitchers set to hit the market in the next couple years, you might think that Jon Lester would simply be one of many. But the Royals are still in the hunt with James Shields, the Tigers and Max Scherzer are already thinking about playoff opponents, the Rays seem set to hold onto David Price for another run in 2015, and while the Phillies have been talking on Cole Hamels, word is that their demands for the lefty's four-year contract are heads and tails above the already large price a rental like Lester might command.
That leaves Jon Lester basically alone at the top, the season's second most valuable pitcher on the trading block in a market full of Jake Peavy types with plenty of could-be contenders looking to punch their ticket to at least the Wild Card game (where having a pitcher like Lester available becomes that much more valuable).
Boston's price for Lester is capped at whatever astronomical demands Tampa and Philly have floated to make Price virtually untouchable and Cole Hamels unrealistic. Of the three, he is the only one who would provide just a couple months of starts (plus the postseason) to his new team, leaving him decidedly the least valuable of the three. Still, that's apparently an awfully high cap to set, and with the Red Sox looking at only a compensatory draft pick if Lester leaves in the offseason, they seem very much priced into a move.
Stark does have some quotes from executives about the danger of letting a player put another team on the back of their baseball card, and the value of attaching the qualifying offer to a free agent, but all that seems pretty ridiculous when we're talking about a player like Lester. Teams will protect their first-round draft picks when looking at mid-level signings, but they barely even come into consideration when talking about $140 million contracts. And if Lester actively wants to stay in Boston, a three-month tour won't dissuade him of that any more than tens of millions of dollars would in the offseason.
What this comes down to is whether the Red Sox are willing to match Lester's market in November. That's how they get him back for 2015. If they aren't willing to do so, then they have to trade him now since walking away from this with just a draft pick would be a total disaster. If they are willing to match that price, then they still have to trade him, since there's no downside to losing his next two months and gaining the significant trade return they can expect.
Whether you want the Red Sox to pay Jon Lester $150 million to stay around through 2020, or let him walk to whoever will, there's just no scenario where it makes sense for the Red Sox to stand pat and keep him for these last two months. The exclusive negotiation period is a phantom advantage that depends on the player accepting a weak bargaining position for no reason, the qualifying offer of negligible impact when it comes to top-tier free agents. For the Red Sox, logic demands a trade.