When Jon Lester made his major league debut on June 10, 2006, he was a boyish-looking 22-year-old standing on the Fenway Park mound, pumping his fist and trying to keep his emotions in check.

That night, Lester pitched only 41/3 innings, because he couldn’t calm down. He threw 102 pitches and walked four.

“Now he’s just going to have to get comfortable,” then-Red Sox manager Terry Francona said at the time.

Lester, who turns 31 next month, is comfortable now. A $155-million contract over six years is likely to help.

But the money is not coming from Boston. The Chicago Cubs will be signing Lester.

Good for Jon. Who doesn’t like the man who grew up before Red Sox Nation, including a full season as the Portland Sea Dogs’ stopper, earning 2005 Eastern League Pitcher of the Year honors?

He is a stand-up guy, both humble and confident. A role model for sure. He beat cancer, pitched for two World Series championship teams in Boston.

And the Cubs will have him for the next six years (seven, if an option is picked up).

Yes, this process dragged out. Reminds me of Lester’s debut in 2006. He arrived at Fenway before 10 a.m. for a 1:20 p.m. start. But then came the rain, and it didn’t go away for hours. Lester’s first pitch was at 6:12 p.m. The Red Sox thought Lester was worth waiting for.

“I thought he showed some of the things we’ve heard about,” Francona said.

And, eight years later, Boston still thought Lester was worth waiting for – and paying for.

But was he worth the $135-million, six-year deal the Red Sox reportedly offered?

Here was one reason against them committing that much money: It was too much of a risk.

History shows that long-term contracts for pitchers don’t work out for the full term. Pitchers get hurt or their ability (and velocity) diminishes. Our current poster boy for such deals is Detroit’s Justin Verlander, whose 4.54 ERA came in the second season of his seven-year, $180-million contract.

But Boston had three good reasons to go after Lester:

n Goodwill. This was the weakest of the arguments, but it’s worth noting that Lester is well-liked and well-respected in Boston. Paying him is not like signing him away from another team (never mind that two-month vacation in Oakland). This would have been the Red Sox keeping one of their own.

n Need. The Red Sox still could use an ace. Maybe Lester couldn’t fill that role solidly for six years, but he could have for at least half of that contract.

n Worth the gamble. Who is to say Lester won’t be effective when he’s 36? Sure the odds are against him, but the Red Sox took a chance when they signed a 37-year-old before the 2004 season. And Curt Schilling worked out.

But we won’t know if Lester could have worked out at Fenway.

All Red Sox fans can say now is thanks for the memories – and begin suggesting other ways for their team to spend that $135 million.

Kevin Thomas can be reached at 791-6411 or at:

kthomas@pressherald.com

Twitter: ClearTheBases