By Dan Roche, WBZ-TV Sports

San Diego (CBS) – Jon Lester has done everything right in this entire free agency process. He’s also learned that things don’t always go as planned or as one hopes . . . at times.

The 30-year-old left hander and his wife Farrah are making a choice that is best for them. Period. And they have earned that right.

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Let’s go back to February. The Sox and Lester were on top of the world. He had just led the Red Sox to their third World Series title in 10 years. He hit Fort Myers thinking he was going to spend at least the next five years in Boston. He loved everything about where he was at in his life and he was in a great position as a free agent. Except, he really didn’t want to be one.

Jon Lester wanted to remain a Red Sox for life. He also didn’t like negotiations. He wanted to walk into a meeting with his agents, Sam and Seth Levinson, sit down with John Henry, Tom Werner, Larry Lucchino, and Ben Cherington and hammer out a deal. He knew what other comparable pitchers had received for deals and he wasn’t looking to break the bank.

His line of thinking was probably something like, “Give me five years at somewhere in the ballpark of $ 100 million and I’m good. Done. Let’s go win another a World Series title.”

Jon Lester is a simple guy. He loves his family, country music, his truck and pitching in a big league uniform. He didn’t want any drawn out negotiations. Just a deal that would satisfy all parties and moving on.

Jon Lester also knew he would get a low offer to start the process. But, he also knew he had uttered the words hometown discount. So he figured it may take until spring training to get to the right numbers. No big deal.


He got a four year offer at $70 million and I think it crushed him. I think he thought that there was way too big of a gap to get a deal done. I think he dreamed of a Clayton Kershaw deal ($30.7 million average annual value), felt like he could get a Zack Greinke contract ($24.5 AAV), but wanted to stay so he would take an Adam Wainwright deal ($19.5 AAV).

But THAT offer in what would be a quick process? Whoa!

And in my opinion — my opinion — from then on things changed.

I just think he looked at things in a strict business manner. The good will, faith and trust that was there? Gone.

I think he still had hope, but it was different.

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Then he was traded and he saw that there was life outside of wearing a Red Sox uniform. He realized he could pitch for another team and enjoy it.

He also vowed that when he became a free agent that he would enjoy the process. He is a respectful man so he would listen to any team that had an interest. He would also see it through from start to finish. He knew this would only happen like this once.

And now here we are. He has choices. He’s now sitting with his wife and figuring out where they want to go; what team and city fits best. I’m sure he’d be happy to go to Chicago or San Francisco or wherever else he feels would be a fit.

I’m sure he also is touched that John Henry has reached out to him several times in person. I bet that helped regain his faith and trust in ownership. And I firmly believe that he still, and always will, love Boston. That will never change.

And if he comes back to Boston I bet he’ll be happy. And there will be good times.

But I just don’t think it will ever be the same. It can’t be.

And, I know it’s a business and that’s life — yadda yadda yadda. And I know the Red Sox will still be good with or without him. They will find pitching and contend. This ownership and front office group are winners. It’s what they’ve done since they bought the team — they have won.

It will just be different.

He’s down to four teams. All good choices, including Boston.

We wait on the decision . . .

Follow WBZ-TV’s Dan Roche on Twitter @RochieWBZ.

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