How Ben Cherington helped make Theo Epstein's smooth Fenway homecoming possible


BOSTON - The Red Sox mishandled Theo Epstein and Jon Lester. We all know that.

There’s a small irony to this pseudo reconciliation at Fenway Park this weekend, then. A notable circumstance for your consideration.

It doesn’t happen without the fine work of another guy in the line of people Sox ownership mishandled: Ben Cherington.

Epstein on Friday likened this Boston jaunt to the college reunion he’s never been able to attend.

“I’m not planning on sleeping much this weekend,” he said.

Theopalooza and the Lester Lovefest are predicated on something simple: Epstein and Lester have been successful since they left Boston. So, too, have the Red Sox. 

Lovers broke up. A few years later, they’re both doing well in new relationships and reminiscing. It’d be an ugly scene were one still a heartbroken mess. Or at least, an uncomfortable scene.


The Cubs have an excellent young core, as do the Sox. The atmosphere at Fenway this weekend wouldn’t be so lovey-dovey otherwise.

Lester and Epstein were able to come back and enjoy this weekend, then, at least in small part, because of someone else the Sox eventually screwed over too: Cherington.

Erratic decision-making has run through the John Henry, Tom Werner and Larry Lucchino era. Sometimes brilliant decision-making, but nonetheless erratic.

There have been choices as excellent as hiring Epstein in the first place, and as nonsensical as limiting him to Lucchino's whims. Choices as shortsighted as lowballing Lester, and as impatient as removing Cherington from power when he was building something that’s proven fruitful.

Today, Lester is still a sore spot for Sox fans, particularly with David Price making more money and doing nothing. But overall, both the Cubs and Sox are getting along fine.

Mookie Betts lining out to Kris Bryant in the fourth inning was some kind of symbolism Friday night.

The Sox had the prospects to trade for Chris Sale and Craig Kimbrel. They developed Andrew Benintendi and Xander Bogaerts and more importantly, held on to them. 

Cherington positioned this franchise to contend for years.

"The Red Sox are finding their own way, as they should," Epstein said Friday at a luncheon for the Red Sox Foundation and the Foundation To Be Named Later. "I was telling a friend, both assistant GMs – Brian O’Halloran and Eddie Romero – are guys I cut my teeth with, hired, developed with, and learned from, and hopefully grew a little bit with along the way. Mike Rikard, the scouting director, is a guy I’ve scouted with a long time. We worked together here. Ben Crockett, the farm director. 

"The guys in the trenches doing the work, a lot of them, I still feel a real connection with. Sam Kennedy is one of my best friends. He’s running the team. I still feel a connection here. Obviously there’s players still here from our drafts and our time here. That’s always going to be the case with any executive. When you move on, part of you remains a little bit, but it’s a whole new direction. The Red Sox are making their own way and doing a really good job."

It’s easy for Epstein to come home under these conditions. 

He snuck into Fenway Park on Thursday night, at Kennedy’s invitation. There was no gorilla suit as he watched the Sox and Yanks, the rivalry Epstein helped epitomize.

On Friday, Koji Uehara and John Lackey shared a tribute video on the big board with Lester. All three former Red Sox tipped their cap to the Fenway crowd. 

Lester, naturally, received the loudest ovation. He’s one of the few established Sox stars who can say they left town without being trashed on the way out.

Lester knows how much fans here wish he had stayed. The reason he doesn’t hear more animosity from them is because they know why he left: the Sox undervalued him in a delusional attempt at pragmatism.

“You play first and foremost for yourself and family, but then you play for the fans as well as the organization,” Lester said. “When you have that support, we’ve been through a lot here — the ups and downs,  a few really large downs and a couple really good ups. I feel like these fans are a part of my family, a part of me and who I am not only as a baseball player but as a person. It’s always nice to see that stuff. It’s nice to be back.”

The first thing Epstein said he did when he got to Boston was drop his bags in his hotel room. The next was take a long run.

“Along the Esplanade and through Back Bay,” Epstein said. “The city was just shining. It’s a special place. I love Chicago. That’s a world-class city. Boston is, too. Every time I come back here, I’m just reminded how lucky I was to grow up here. 

“Everyone out on the streets was in a good mood, the city was looking great, I got an unsolicited high five because I ran past another jogger going the opposite direction. It was cool. This is the best city in the world to walk around and go for a run in.”

The ninth inning of Friday’s 5-4 Sox win was the most electric at Fenway yet in 2017, the capper to an undeniably special day.

Epstein and Lester have moved on and remained incredibly successful. The Sox found their own way in their absence. 

But if the Sox were still struggling while Epstein and Lester dominated, this weekend would have a different tone. 

It’s worth a head shake, if nothing else: the guy who helped ensure Epstein and Lester could hug it out, Cherington, was mishandled by the same set of bosses.

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