Ask about the 2006 contract extension many feel lost Josh Beckett millions in the open market, and the pitcher will usually give a hard-to-argue-with analysis:

“I will have made close to $50 million by the time I’m 30 years old.”

Thanks to Monday afternoon’s start in Chicago, that figure might be conservative.

By taking the mound against the White Sox Monday, Beckett started in his 28th game this season and thereby was able to have the $12 million team option vest for the 2010 season. The clause in the hurler’s contract was activated either if he started in 28 games in ’09, or 56 games combined in ’08 and ’09. Beckett started in 27 games last season.

The only way the option wouldn’t be triggered is if Beckett finishes the ’09 season on the disabled list.

Beckett inked his current contract extension in July, 2006 at what would be one of his lowest points of his Red Sox career. That deal was worth three years, $30 million plus the team option for ’10. When the deal was agreed upon, the righty owned a 5.12 ERA, the highest mark he would ever have any season as a Red Sox past May 16.

If the contract wasn’t signed, Beckett could have potentially made millions more in the free agent market since he would have become a free agent following the 2007 season. He would have been heading into the open market having not only finished second in the American League Cy Young voting, but having turned in a post-season in which he went 30 innings, allowing just four runs while striking out 35 and walking just two in leading the Red Sox to a world championship.

Many believe if he did go to free agency following the ’07 season, Beckett would have been in line for a deal similar to the one given to Johan Santana that offseason, a contract that came out to $137.5 million over six years.

Besides any insecurities that went along with getting off to a slow start with the Red Sox in ’06, there were good reasons Beckett inked his extension when he did. He was told while with the Marlins that getting his pitching shoulder insured might be difficult, potentially leaving some teams with uncertainty in terms of committing to the then-26-year-old. And there was also the knowledge that he would be young enough to get at least one more big deal if all worked as planned throughout the life of the extension.

(It should be noted that while Beckett wasn’t able to get insured by Lloyd’s of London to protect his pitching shoulder in ’05, he had undergone an MRI on his pitching elbow following the ’07 season at the request of the Red Sox for insurance purposes. As a result of the examination, the Red Sox were able to secure insurance on Beckett’s contract.)

Since signing his current contract, Beckett has the fourth most wins in the majors (51), the ninth-most strikeouts (605), and a 3.87 ERA. He has also developed into the leader on the Red Sox’ staff, both in performance and preparation, with the organization holding up the right-hander’s in-between-starts routine as the example for all their young pitchers.

As for life after ’10, Beckett presented the groundwork for his approach early on in this season’s spring training…

“I honestly don’t try to think about it. I think if I deserve it I’ll be back here,” he said. “If they think I don’t, I’ll have to go elsewhere and try something else. Obviously I would like to stay here, but (thinking about it) is really not in my core.

“At the end of the year hopefully we’ll sit down and maybe have a talk with (Red Sox general manager) Theo (Epstein), me and my agent (Michael Moye) and see what they’re thinking about. I want to see where they’re going, if I’m even in their plans. If I’m not it was an awesome run. I really haven’t sat down and thought about it too much, but at the end of the year we will sit down and at least have a talk. Even if nothing comes of it, just to say, ‘Are we in the plans? Are we looking to get younger?’ It’s really up to them. I would like to stay here. I love playing in Boston. I can’t imagine another organization that would go so far out of the way to make my job as easy as possible. They realize our jobs are very demanding and very hard, and they do everything they can.”