The Chris Sale / Jon Lester Conundrum

Is there any pitching-related matter with the Boston Red Sox that Shank can't hang around the neck of the Jon Lester trade?

OAKLAND, Calif. — The Red Sox locked up Xander Bogaerts and Chris Sale in the last two weeks, committing $265 million of John Henry’s money to a couple of players that would have been free agents at the end of this season. It’s a serious commitment that should warm the heart of Red Sox Nation.

I am a fan of the Bogaerts extension, but not so sure about Sale, who was scheduled to pitch Tuesday night in Oakland.

Sale was hoping to stop the bleeding after the Sox lost four of their first five games, getting outscored, 41-24. Alex Cora’s five-man rotation surrendered 26 earned runs in 21 innings in those five games, yielding 11 home runs. Aggregate ERA: 11.14. It was a big bowl of yuck.

But I’m thinking bigger picture today (first time for everything! - ed), wondering if the contract extension to Sale was a sound baseball decision, or perhaps overcompensation for past sins. Did the Sox let their mistake on Jon Lester rush them into a mistake on Sale?

Seems like now is never too early for Shank to preemptively second guess and pile on, is it?