Red Sox, Kevin Youkilis Near Extension; What About Jon Lester?

Other than a dalliance with Mark Teixeira, Boston's offseason has been almost entirely about tying up loose ends -- keeping the core that has brought so much success lately intact and building up the depth around it.

The Red Sox kicked off their winter by locking up American League MVP Dustin Pedroia for the next six years. In recent weeks, they've added a host of familiar faces to their bench and pitching staff -- including John Smoltz, Takashi Saito and Rocco Baldelli. Now, they're "close" to a contract extension with Kevin Youkilis that could keep him in Boston for the next five years and pay him $53 million, according to Tony Massarotti of the Boston Globe.

This is yet another team-friendly deal for the Red Sox, who are getting up to three of Youkilis' free-agent years at the cut rate of just over $10 million a season and will avoid any commitment to him beyond his age-34 season. It's not quite the steal that Pedroia's extension was, but then Youkilis was closer to free agency and could command more.

Youkilis' contract status was the subject of much speculation this winter. His agent even cast doubt that an extension would get done last month. Now that speculation figures to shift to all-world closer Jonathan Papelbon and emerging starting pitcher Jon Lester.

Never afraid of the limelight, Papelbon might seem like Boston's top priority, but if I was general manager Theo Epstein, I'd be focusing most of my energy on Lester.

Papelbon has stated in the past that he's out to make as much money as possible, so it's unlikely the Sox would be able to lock him up to a similar club-friendly contract. Frankly, I'm not sure they should given Papelbon's past health problems and the high attrition rate for closers.

Lester, 24, is three years younger than Papelbon, and has the potential to become one of the rarest commodities in baseball -- a true left-handed ace, with the body type and the electric stuff to match that moniker. Maybe the Sox should be cautious with Lester -- I'm hardly one to second guess the best baseball operations staff in the majors and the innings jump from 2007 to 2008 gives pause for concern.

But other than Pedroia, there isn't a guy on the Red Sox roster who seems more likely to be a centerpiece franchise player than Lester. If the Sox feel similarly, don't be surprised if Lester becomes the next Boston player to secure his long-term financial future.