It is perhaps the most important skill a baseball front office can possess these days -- understanding when it's the right time to swoop in with contract extensions.

Former Red Sox general manager Theo Epstein was extraordinarly good at the practice, saving the organization millions of dollars by keeping key players under team control. It has been a particularly important exercise when it comes to a team attempting to find a core group of pitchers to call its own. Examples …

The Red Sox signed Josh Beckett at his then-career low point, in July 2006, ultimately preventing the righty from hitting the free agent market after a spectacular '07 season. Beckett helped lead the Sox to a World Series in the first season of his three-year, $30 million deal (with a $12 million club option for '10 that was picked up) in 2007; following that season, Johan Santana -- who was eligible for free agency after '08 -- found himself a six-year, $137.5 million deal with the Mets.

Clay Buchholz signed his current four-year, $29.945 million extension (that has club options for '16 and '17) as a 26-year-old coming off a 17-win season, in which he totaled a 2.33 ERA in 28 starts. The highest salary the Sox will have to pay Buchholz is $12 million, with the options for '16 and '17 going for $13 million and $13.5 million, respectively.

Then there's Jon Lester.

If Lester hadn't signed his five-year, $30 million extension (with a $13 million club option for '14) in the spring of '09, he would have been hitting the free agent market this season. (As a quick aside, if the lefty finishes in the top two of Cy Young voting his '14 option disappears.)

And while '12 represented a dramatic turn for the worse, with Lester finishing at 9-14 with a 4.82 ERA in 33 starts, he'd still represent a highly valued pitcher given his age (28), health (good), and pre-2012 track record. From 2006-11, Lester totaled the fourth-most wins of any lefty in baseball (76), while managing the sixth-best ERA (3.53) and batting average against (.245). The Red Sox were also a gaudy 98-57 over that stretch with Lester on the mound.

From 2008 -- when he emerged as an anchor of the rotation -- through 2011, he joined CC Sabathia and Roy Halladay as the only pitchers in baseball with at least 15 wins and a sub-3.50 ERA. From that vantage point, some teams would almost certainly view 2012 as an aberration when it came time to determine the left-hander's worth on the open market. 

Simply put, even with the downturn of '12, Lester was going to put a dent in somebody's payroll if that extension hadn't been signed. And, whether or not you view the southpaw as a top-of-the-rotation pitcher, if he does leave, that's another significant hole for the Red Sox to fill.

So, with history as a guide, the question should be asked: Might it be time for the Red Sox to approach Lester once again?

The Red Sox do still have two more years of control of Lester's fate (assuming that the 2014 option remains in play), but, from a team perspective, the best time to broach an extension with a player of perceived value is when he is still young and/or has insecurity due to performance.

No talks about an extension have been initiated by either side, but with the Red Sox' blueprint for a resurgence undoubtedly leaning heavily on the foundation of a solid starting rotation, it's a debate at least worth surfacing.

"We'll see," said Lester on the final day of the '12 season. "This probably isn't the best year to talk about it. I'm always open. I'll listen. We can always talk. I have no problem with dialogue. I have no problem with sitting down and seeing where they're at, and seeing where we're at. I would imagine it's one of the last things on their plate right now, just with all the stuff going on. I still got really a year before we kind of have to figure things out as far as an option or anything like that. Like I said, it's probably not something high on their list right now.

"I'm always open to listening. We can always talk. That doesn't mean they're going to be close, or we're going to be close, or a deal is going to get done. I'm always open to seeing where we're at. I'm fine with that. I would be fine with trying to work something out. If we had a better year and didn't have so many needs, especially with me being under control for the next two years, that's not something that's a priority. We have other holes we have to fill first."

With another year of guaranteed money from the Red Sox awaiting him in '13, perhaps Lester would rather take the approach of getting things right and forcing the issue after next season. After all, on his former track, he was at least in the conversation when it came to pitchers benefitting from the Matt Cain extension of six years for $127.5 million.

But, as indicated to at least some degree when he jumped at his first extension, Lester clearly enjoys the security of contractual certainty. As he points out, part of it stems from the uneasiness that comes with being a cancer survivor, with the reality of continuing to support a young family always looming as well.

This time would be different, no doubt. Any extension undoubtedly be Lester's largest contract of his career. But for the team, the motivation remains the same as last time -- eliminating anxiety when it comes to executing the always uncomfortable task of putting together a solid starting staff for years to come.

"The first one for me is like icing on the cake," Lester said. "The first one is a chance to set my family up for the rest of our lives. For the guy who has the ability and mindset to go year to year, I applaud them because I couldn't do it. Especially with my background, I wouldn't feel comfortable doing that. To be able to get that first one and be comfortable, be able to settle down, it makes it a lot easier. The second one, I don't know how to approach that or what the mindset is. It's the job of (agents Sam and Seth Levinson) to prepare me and let everything else dictate the situation."