It's simple. The Red Sox were counting on Lester not having the absolutely best season of his career in his platform year, while Lester bet that he could. Lester won. The real problem here is that Lester probably saw that initial offer as a slap in the face, and i don't blame him. Those who assume he would have signed for way below market value, however, are either looking for mental masturbation help so they can whine, or they wanna be a jackass about it (looking at Jacko). The point is that the Sox could have handled the negotiations better, but if anyone here tells me they expected Lester to put up the season that he did, they're lying.