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Nick Cafardo | On baseball

How the Red Sox lost Jon Lester to the Cubs

SAN DIEGO — Joe Maddon had only spoken to Jon Lester once in all the years the two competed against one another in the American League East. Now they will speak to one another every day after Lester signed a six-year, $155 million deal with the Chicago Cubs.

The Red Sox got as far as $135 million over six years. There was a $20 million hometown discount to be had, but it never happened. Lester had said last winter he would give the Red Sox a discount, but the gap was either too much or Lester just wanted a change.


Earlier in the night he had told San Francisco Giants he was not going to choose them. According to a Giants team source Lester never gave the Giants a chance to make their final offer.

And so the Red Sox, who tried to get back into the race, seemed to be running uphill after their lowball offer of $70 million over four years last March.

They never seemed to recover fully from that. Lester refused to discuss a deal with the Red Sox a couple of different times, including at the All-Star break.

Without an agreement, the Red Sox traded Lester to Oakland for Yoenis Cespedes. Lester kept saying all along that he had no hard feelings toward the Red Sox and wouldn’t rule out a return to the Red Sox.

Red Sox ownership made two different trips to Lester’s Atlanta home. John Henry paid a personal visit last Friday.

But the final number didn’t come close to the Cubs’ final offer.

In the end there were no seven year offers as had been reported. There weren’t four teams willing to go $150 million and over.

A bogus report had the Dodgers involved and they never were except for a cursory inquiry.


It came down to Boston or Chicago. Hometown discount or new frontier.

It came down to a chance to be a part of something big - a possible World Series championship down the road for a franchise that hasn’t won since 1908.

And Lester took the extra $20 million and the destiny factor and made what appeared to be a very tough decision.

It was a tough decision for the Red Sox. They put a value on every player and they extended that value to Lester. Once it got to a point where they didn’t want to keep pushing the envelop, they stopped. And the Cubs had him.

In the end, Lester did go to the highest bidder. Most players do. He turned out to be no different than anyone else.

He’s back with Theo Epstein, Jed Hoyer and Jason McLeod, three Cubs executives who used to be Boston executives.

Three executives who you worked for most of your tenure in Boston.

Three guys who may have said something and done something nice for you when you were battling cancer as a young pitcher.

He’ll be with a young, rising team that will be explosive offensively once they mature.

And there’s that Cubs’ legacy.

So after the money other “things” do come into play.

He couldn’t have gone wrong pitching for John Farrell in Boston. He couldn’t have gone wrong pitching for Bruce Bochy in San Francisco or throwing to Buster Posey.

He couldn’t have gone wrong playing for Maddon, a man he admired from afar for so many years of the Boston/Tampa Bay rivalry.


The popular Maddon has always been an admirer of Lester’s. He admired the battler, the gutsy performances against his former Tampa Bay team.

“I spoke to him on the phone once,” Maddon said of the Cubs’ courtship of Lester. “I’ve never spoken to Jon before that. I always admired his work from a distance. This is a guy when the game is really big he was always at his best.”

Maddon said he recalls having a “great conversation, again, because I’d never really spoke with him before. Like I said, as an opponent, he was always at his best when it seemed to matter the most. The thing I’ve always garnered from watching him pitch, if you’re going to get to this guy, it’s one of these typically great pitchers, you want to get to him early. If you permit him to settle down, you could be there the seventh or eighth inning.

“He’s come through some physical issues, also. But you can’t have any more respect for a baseball player than we do for him now.”

During the conversation, Maddon found out Lester likes to hunt and fish.

“At that time I didn’t know that Davey Martinez (Maddon’s bench coach in Tampa Bay) was going to be part of our staff. So now we can line up these hunting trips on the road. As part of the Rays, our guys liked to hunt and fish a lot, like to shoot things. We would set things up on different road trips. Like a couple of years ago Wade Davis shot a black bear in Toronto prior to the playoffs.


“I thought that was outstanding,” Maddon added. “That gave me even more confidence putting him in a game, like in the seventh or eighth inning, facing a normal right-handed hitter, he shot a black bear, 300-pound black bear. I like when the guys do things like that. He relayed to me the fact that he likes to hunt and fish. I assured him that I don’t, but I respect it.”

At dinner the other night at a popular steakhouse, Maddon checked his phone frequently to see if there were any messages regarding Lester. There were none. But he wanted so much to get that text from Epstein that finally said, “We got Lester!”

Maddon, standing in the lobby of the Grand Hyatt Tuesday night, finally got that text from Epstein, a day later.

The National League should be good for Lester. No DH. Weaker lineups. On the flip side, Lester has to hit and he’s 0-for-50 in regular season and postseason. He also has problems throwing to bases and that will be tested with teams that often have to bunt to move runners along.

Did the Red Sox botch this one? Probably so. They probably could have signed Lester for the Homer Bailey $105 million deal back in March. The market took off on them. They miscalculated.


And in the midst of Lester having one of the best seasons of his career, after a fabulous 2013 postseason, the price went up and up.

So now the Red Sox have lost their money lefty for good. Ben Cherington will have to move on to free-agent James Shields, or trade for ace types like Philadelphia’s Cole Hamels and Detroit’s David Price, and also sign one or two middle rotation pitchers after that.

Big mistake? Probably. They are saved by a deep pitching market. They will move on from Lester and replace him.

Or so they think.

Related coverage:

■  Jon Lester chooses Chicago Cubs over Red Sox

■  Jon Lester’s career highlights with Red Sox

■  Notebook: If Red Sox land Cole Hamels, it may be costly

■  Shaughnessy: On Jon Lester watch, stakes are high and information scarce

■  Red Sox make offer to pitcher Justin Masterson

Nick Cafardo can be reached at cafardo@globe.com.