Getting the best of Lester?

Michael Silverman of the Boston Herald writes an interesting piece on Jon Lester's five-year, $30 M signing with the Red Sox and how it miffs agent Scott Boras.

It’s quite easy to understand why the Red Sox and the players love these deals. Not only do the Sox have cost certainty with such early proactive deals, but they also bought out one to two years of free agency with Kevin Youkilis [stats], Dustin Pedroia [stats] and Lester. For example, the latter is on a career trajectory that has the potential to mirror that of CC Sabathia, who waited to reach free agency and then inked a seven-year $161 million deal with the Yankees.

There are no guarantees with anything, of course, and there is no doubting the sincerity of such eager Red Sox players and others who opt for early deals (Ryan Braun, Evan Longoria, Troy Tulowitzki) when they say they love their deals because of the financial security they grant them.

Boras, who has only had a couple of clients (Jeff Weaver, Carlos Baerga) sign such deals in recent years, believes players who don’t wait for the free agency status that comes after six years in the major leagues deprive themselves of the opportunity to maximize their earning potential, as well as the earning potential of other elite talents, by deferring that long-range freedom for an early cash grab.

“You have to ask the question, why would teams that have four years of control over a (two-year) player offer six years security?” he said. “The math doesn’t work unless there is a substantial discount.”

It's a good piece, and in what are less than stable economic times you have to wonder if more teams continue to offer these types of deals to young stars.