I do not think Lester is comparable to Ellsbury. Lester wants to be here and is willing to talk about a long term extension before free agency, while Ellsbury clearly wanted the biggest offer, and needed to hear all of those offers before deciding. Lester has performed consistently, and he has been healthy -- Ellsbury has not. The Red Sox believed they had a viable replacement in Bradley, while you really cannot replace a guy like Lester. If the Red Sox signed Ellsbury after 2013, they would not have had flexibility to make other signings. In 2014, there will be plenty of payroll available for Lester.
100 million for Lester is much more reasonable for all those factors than Ellsbury at 150.