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FORT MYERS, Fla. -- John Henry long ago declared that pitchers in their 30s represent bad investments, and the numbers largely support this hypothesis. But there are always exceptions, and Henry believes Jon Lester was one of them.
In a discussion about the merits of signing ace Chris Sale to an extension before he reaches free agency, Henry admitted that letting Lester walk in the middle of the 2014 season (and then not signing him that winter in free agency) represented a huge mistake.
"I think we blew the Jon Lester -- we blew that signing in spring training," Henry said on Monday. "So for reasons that are pretty apparent now, which I won't go into, but they're apparent. But it wasn't... you can see what's gone on in free agency. The price of WAR has gone up radically (enough) that it's difficult whether it's a pitcher or a position player entering into a really long term contract with high dollars. And we haven't had a great track record. We've done better with pitchers perhaps than we have with hitters and really long term contracts."
Red Sox fans need no reminder of how 2014 unfolded. The Red Sox opened negotiations during Lester's walk year with a four-year, $70 million lowball offer in spring training. Countering high enough to land at a happy middle would've opened Lester to charges of greediness. So the two sides shut down negotiations, the Red Sox clubhouse rallied around the left-hander and against management, and the entire problem tore the team apart until GM Ben Cherington pulled the plug by dealing away Lester and John Lackey, among others.
The fallout was significant. Cherington and manager John Farrell eventually lost their jobs. The Red Sox invested $217 million in left-hander David Price, who ended up battling the media before leading the Red Sox to a championship last year. The team also shipped top prospects Yoan Moncada and Michael Kopech to the White Sox for Sale.
Now they find themselves trying to decide what to do with Sale in a walk year, while hoping to avoid the mistakes of 2014, when they chased Lester away. He has gone on to win a World Series with the Cubs, and the Red Sox may soon open the bank for his replacement, even though Sale is entering his 30s, too.
"I don't know," Henry said. "You guys should decide whether my thinking has changed."