Cherington to Dombrowski a critical mistake by Sox?

Answer lies in team’s future

According to an industry source this week, Ben Cherington does not figure to be in the running to replace Dave Dombrowski atop the Red Sox organization. And that’s a shame. Looking back, the argument could be made that the Red Sox should’ve never made the move from Cherington to Dombrowski in the first place.

It was June 2015 when principal owner John Henry

made the declaration that Cherington “is going to be the general manager of this club for a very long time.” Henry’s words killed any speculation that Cherington might be in danger, though the speculation wasn’t all that rampant.

Most of the talk was about John Farrell and whether or not his voice was still carrying much weight in the locker room. It probably wasn’t. But the Sox had been reluctant to make a change at manager, still hoping that Farrell’s pitching expertise would lead them to a turnaround.

The failures of Hanley Ramirez and Pablo Sandoval

led Cherington to take some heat too.

The Red Sox were having a historically bad year, about to pay $2.4 million per win for a 78-win team, the most expensive disappointment since 2012, when they paid $2.4 million per win for a 69win team (though the disaster of 2019, when they’re on pace to pay $2.9 million per win for another non-playoff team, is worse than both those figures).

But Cherington had still done more good than bad in his time with the Sox. The culture in the front office had a healthy and functional feel around it. The processes that had been designed for long-term growth were still in place. And Cherington made it clear to Henry that he was all-in on determining what went wrong in 2014 and 2015, which is why he hired former Angels general manager Jerry DiPoto as a consultant, with Henry’s approval.

Then in August, Dombrowski made a confusing exit from the Detroit Tigers. Similarly to his ending in Boston, he had won four straight division titles before being fired. There was speculation that Dombrowski had planned all along to reunite with Henry, speculation furthered by a statement made by Tigers owner Mike Illitch at the time.

“I’ve decided to release Dave from his contract in order to afford him the time to pursue other career opportunities,” he said.

And just like that, Cherington went from the longterm GM of the Red Sox to resigning from an organization he worked for since 1999.

Drastic change

Cherington never believed in the president of baseball operations structure, the one the Tigers were using in Detroit.

“I talked to Dave briefly yesterday on the phone, and we didn’t spend a lot of time on it,” Cherington said when he walked away in Aug. 2015. “He made it clear to me, and I heard this from John (Henry) also, that he was coming in as the president of baseball operations, chief baseball officer, whatever you want to call it. In that position, he was being given sole decision-making authority for baseball matters, as I would expect he would.”

In Detroit, Dombrowski was the president but originally kept his general manager, Randy Smith, in his role. Until six days into the first season, when Smith was fired and Dombrowksi made himself the GM.

Cherington had no desire to go through that.

“We all know baseball operations is a big job, there’s a lot to do,” Cherington said at the time. “I’ve always felt it’s about a team of people. It’s not about one person. We didn’t get into a detailed conversation about exactly what my role would have been. I do know that the only way it was going to work for Dave or for me or ultimately for the Red Sox is if I was all-in and fully committed to that vision. I came to the determination that I wasn’t.”

Cherington always preached teamwork. He empowered those around him and created a family feel with his assistant general managers in the front office. One of them, Mike Hazen ,has since gone on to become the general manager in Arizona, where the Diamondbacks are trying to build a sustainable success the way Cherington had tried in Boston.

“It’s never one person doing everything,” Cherington said back then. “It’s been a group making decisions. It’s not about needing to only exercise my vision. This is simply about what’s best for the Red Sox. The Red Sox need everyone allin on going forward. That’s what Dave needs. For a variety of reasons, I just didn’t feel I could be. I’ve been happiest in my career in baseball when I’ve been part of a group making decisions, and that leads to success.”

Adding to the confusion was the announcement that Larry Lucchino was stepping down from his role as president and CEO just a week before Dombrowski was let go in Detroit.

ESPN reported that it was just a coincidence, that the Sox had no plans to pursue Dombrowski.

Then the Sox hired Dombrowski in a role as president of baseball operations two weeks later.

“Tom (Werner) and I wanted to see if there was a fit for Dave within the Red Sox organization,” Henry said in 2015. “Ben did not object. Would our philosophies coincide in the present day?… We all left there thinking we could substantially strengthen the organization with Dave as president of baseball. We realized that our baseball views were, in fact, going to be in sync.”

Henry praised Dombrowksi for building organizations “the right way.”

Looking back, that seems odd given Dombrowski’s long history of going all-in at the top, often at the price of the owner’s pocketbook and the farm system’s depth.

“Dave tends to balance scouting, data analytics and player makeup and all the tools in his tool box,” Henry said. “We hoped that Ben Cherington would remain as general manager but we knew there was a substantial risk he would not.”

The Sox had moved on, having seemingly stolen Dombrowski from Detroit and blindsided Cherington just after announcing to the world that Cherington was the long-term leader of the franchise.

With the benefit of hindsight, we can wonder if it was the wrong choice.

Bad transition?

Under Dombrowski, the Red Sox won the division three straight years and captured a title in 2018. That makes it difficult to call his hiring a mistake. Three years from now, we should have even more clarity when we watch the Sox try to dig themselves out of exorbitant financial commitments, a bottom-ranked farm system and a roster that must rely on an injuryplagued starting rotation for the next three years, when David Price, Nathan Eovaldi and Chris Sale are all under contract with top-tier salaries.

Then there’s the issue of front office culture. Multiple reports this week confirmed whispers around the industry that Dombrowski was not running a well-oiled machine in Boston, that those around him questioned his creativity and willingness to cooperate with others.

The Detroit Free Press added another layer, reporting that Dombrowski had the same reputation with the Tigers.

“He is demanding to work for — none of his assistants in Detroit went to Boston with him, though it’s also unknown if any were offered the chance — and largely builds his teams on his terms,” the Free Press wrote.

Never were such claims presented about Cherington.

His baseball decisions will always be questioned, but at his best he was arguably better than Dombrowski.

In 2013, Cherington built a Red Sox team that won 95 games and cruised to a World Series title in a postseason that was smooth from beginning to end (knocking off Dombrowski’s Tigers in the ALCS when the Tigers’ bullpen collapsed – sound familiar?).

And Cherington did it while spending just $176.5 million. It was a masterful performance in roster building, with the 40-man bunch costing a total of $1.8 million per win, the least amount the Red Sox have spent per win in any year from 2010 through 2019.

Like Dombrowski’s Sox in 2018, Cherington’s 2013 roster had the fingerprints of both the current and former general manager all over it. No way they would’ve won without Theo Epstein’s guys in 2013, just like there’s no way they would’ve won without Cherington’s guys in2018.

The same can be said for Cherington’s guys in 2013 (Mike Napoli, Shane Victorino, Jonny Gomes, Stephen Drew, David Ross, Ryan Dempster)

and Dombrowski’s guys in 2018 (Sale, Price, Eovaldi, J.D. Martinez, Steve Pearce, Mitch Moreland).

But Cherington is often remembered poorly around Boston, largely because he thought David Ortiz could get the best out of Hanley Ramirez, or because he saw the trend of over-paying starting pitchers and thought he struck a bargain on Rick Porcello, whose underlying numbers were all trending up, or because the market was over-valuing Cuban prospects and Cherington utilized Henry’s resources to take a gamble on Rusney Castillo that ultimately failed.

Certainly the biggest mistake was that Cherington couldn’t develop starting pitching. While he departed with a farm system that was widely considered one of the best in baseball, the Sox failed on just about every homegrown starting pitcher under his watch.

But has Dombrowski done any better? Maybe in time we’ll look back and say Tanner Houck turned into a nice reliever (as farm director, Cherington found Matt Barnes and Brandon Workman ) or Jay Groome overcame his off-the-field concerns and recovered from Tommy John surgery to be a productive starter.

If not, Dombrowski is equally as guilty as failing to develop anybody on the mound.

The farm system is considered one of the worst. The financial commitments will leave the next general manager with razor-thin financial flexibility and difficult decisions ahead.

Dombrowski and Cherington each won a World Series in Boston. Each lasted only four years in their roles at the top. But only one of them left the Red Sox in good shape for the years ahead.