Two years ago, amid the chaos of a season crumbling around them and the eventual fire sale that paved the way for a championship, the Boston Red Sox very quietly let teams know that Jon Lester was available.

He was in the midst of his worst season, coming off the beer-and-chicken mess of 2011, stifled by manager Bobby Valentine, and after initial discussions with the Atlanta Braves didn’t go far, the Red Sox found a more-than-willing trade partner: the Texas Rangers.

The talks went beyond tire kicking, multiple sources with knowledge of the negotiations told Yahoo Sports. Names were exchanged. Permutations went back and forth. And for the second time, the Red Sox were threatening to deal Lester to the Rangers. The first time, of course, was as the third piece of the 2003 trade that almost sent Manny Ramirez to Texas and Alex Rodriguez to Boston.

Eventually, the 2012 talks fizzled. Texas got bounced in the wild-card game. The Red Sox rode Lester’s rebound year into the 2013 postseason, where he posted a 1.56 ERA and won a pair of World Series games. And now Boston is faced with an altogether different choice, one of its own doing, frankly, because its owners’ hubris put general manager Ben Cherington in an awfully difficult position.

Because for the third time, the Red Sox are entertaining the idea of trading Lester, now 30, now fully developed, now in the midst of the best season of his career. And the difficulty is that if the Red Sox hadn’t insulted him this spring with a ludicrously under-market contract offer in the first place and followed up throughout the season with paltry increases far from commensurate to his growing value, they wouldn’t have to worry about the wisdom in trading him now – and if it destroys any chance of him re-signing once he hits free agency this offseason.