Transaction Analysis

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Hired Dave Dombrowski as president of baseball operations; Ben Cherington resigns as general manager [8/18]

Ben Cherington was the architect of a Boston Red Sox team that won the World Series 665 days ago. As of last night, he’s on his way out as general manager of that very same franchise.

There’s plenty of time to speculate as to how Dave Dombrowski, now Boston’s president of baseball operations, figures to change the Red Sox moving forward. The days before us will be filled with talks of trading prospects, Rick Porcello jokes, David Price speculation and whispers as to what’s next for Cherington and his staff. We’ll get to some of that in a moment.

Any discussion of Tuesday’s tumultuous night at Fenway Park, should, however, begin with a look at Ben Cherington’s time in Boston, and how he became the owner of one of the strangest legacies not just in Red Sox history, but of any general manager in recent memory.

Cherington had been with the Red Sox for 16 years, starting as a scout under Dan Duquette, working his way up the ladder under Theo Epstein and eventually serving as his like-minded successor. All in all, the four Cherington-led Red Sox teams finished with a 290-315 record, winning the World Series in 2013 but suffering 90-loss seasons in 2012 and 2014 and threatening for 90 losses again in 2015.

As Bryan Grosnick pointed out last week, Cherington is now just the fourth Red Sox GM to leave office with a losing record, joining Buck Harris, Pinky Higgins and Dick O’Connell to form a barbershop quartet of futility.

Yet that 2013 title counts, despite what Dan Shaughnessy would have you believe, and while Cherington inherited much of the core of that team, his savvy moves in free agency pushed that squad over the top. Add in that Cherington’s rebuilt Boston’s minor league system to be among the very best in the game despite graduating talent like Xander Bogaerts and Mookie Betts, and it’s easy to see why Red Sox fans should have mixed emotions about the news that Cherington is moving on.

The excellent Chad Finn produced a comprehensive breakdown of Cherington’s transactional track record earlier this season, but here’s an even briefer recap of some of his most prominent triumphs and failures:

Good

• The “Nick Punto trade,” in which Cherington found a willing taker for the contracts of Carl Crawford and Josh Beckett, also forking over Punto and the valuable Adrian Gonzalez to the Dodgers for a package of prospects.
• Signing Shane Victorino, Mike Napoli and Koji Uehara with some of the money left over from the Punto deal. While neither of the first two players contributed much beyond 2013, they all played integral roles in Boston’s most recent title.
• Not trading Bogaerts or Betts at a time when many were clamoring for a deal for a major pitcher or star. This could still turn out to be the wrong move, but it looks wise as of now.
• Getting Eduardo Rodriguez for 20 innings of Andrew Miller.

Bad

• Trading Josh Reddick and prospects for Andrew Bailey, who threw 46 subpar innings for the Red Sox.
• Trading an affordable year of a productive John Lackey for Allen Craig and Joe Kelly (and his great stuff).
• Trading Jon Lester for Yoenis Cespedes after (allegedly) botching early contract negotiations with Lester, then flipping Cespedes for Rick Porcello, failing to land Lester in free agency and subsequently signing Porcello to a four-year extension.
• Signing Hanley Ramirez and Pablo Sandoval to long-term deals, assuming that Ramirez could handle left field and Sandoval wasn’t regressing. These moves could still work out, but neither—especially Ramirez—looks likely to do so.

Even some of Cherington’s good moves came with caveats. While the Punto deal gave the Sox financial freedom, none of the prospects they received panned out. Dustin Pedroia’s seven-year extension was lauded when signed in 2013 but looks less impressive now. Trading for Jake Peavy helped secure the ‘13 pennant, but cost Jose Iglesias. A.J. Pierzynski...well, no, that was just terrible.

Still, as I wrote in June, Cherington’s most damning failure was likely his utter inability to construct a competent major league pitching staff this season. He missed on Porcello and he really missed on Porcello’s extension. He missed on Justin Masterson. He missed on Kelly. The Wade Miley trade and extension look just so-so. And the middle relief corps of Craig Breslow, Alexi Ogando, Robbie Ross Jr. and Tommy Layne has been atrocious.

Factor in the Ramirez and Sandoval contracts, and it’s not totally surprising that we’re where we are today, despite John Henry’s comments in June that Cherington would be the general manager “for a long time.”

Where does this leave the Red Sox now? In a pretty odd place, all things considered. The rotation is in shambles, the bullpen needs a major overhaul, Ramirez needs a position and some of Cherington’s recent contracts have limited the financial flexibility the GM once worked so hard to create. At the same time, there’s a young nucleus of Bogaerts, Betts, Eduardo Rodriguez, Blake Swihart, Rusney Castillo, Jackie Bradley Jr., Brock Holt and other players that looks quite promising. Boston also has an elite farm system with talent like Yoan Moncada, Rafael Devers, Manuel Margot and several mid- to back-end starting pitchers in the upper minors. There’s a lot of work to be done, but the Sox aren’t starting from scratch.

And such is the organization that Dombrowski will inherit just a few weeks after being “released from his contract” by the Detroit Tigers. Dombrowski was with Detroit for nearly 12 seasons, taking a perennial bottom-dweller and transforming it into a juggernaut that won four consecutive AL Central titles between 2011-2014 and made the World Series twice, in 2006 and 2012. After worst-to-first-to-worst-to-probably-worst-again campaigns from 2012-2015, it should come as little surprise that the Sox would crave the stability Dombrowski achieved with the Tigers.

Dombrowski cut his teeth as GM of the Expos in the early 90s, was the architect of the 1997 Florida Marlins team that won a championship and worked under Henry for several years when Henry purchased the Marlins in 1999. That level of familiarity made him an obvious potential match for the Red Sox when Larry Lucchino stepped down, yet the suddenness with which Boston’s front office has changed its complexion is fairly staggering.

What does this mean for Boston’s roster construction moving forward? Insert your “only time will tell,” Tom Rinaldi-esque cliche here, but there are a few changes that immediately come to mind.

Dombrowski, as we all know, is viewed as more of an old-school baseball guy than a statistically inclined GM. He has a penchant for signing free agent pitchers to sizeable deals—something the Red Sox have shied away from in recent years—as well as locking up his own stars with mega contracts. He used a stars-and-scrubs approach to build a Tigers roster that’s featured the likes of Miguel Cabrera, Prince Fielder, Victor Martinez, Max Scherzer, Justin Verlander and David Price in recent years, but has suffered from poor supporting casts and atrocious bullpens.

Most notably, Dombrowski hasn’t balked at trading vaunted prospects and young players for established major league stars: something Cherington shied away from during his tenure. Many times, these deals worked out, such as when he traded Cameron Maybin and Andrew Miller for Cabrera, or Jacob Turner for Anibal Sanchez. Other times, especially earlier in his career, his aggressiveness didn’t pay off: the man has also traded away Randy Johnson, Trevor Hoffman and Johan Santana.

Still, assuming Dombrowski will come in and blow up Boston’s young core isn’t quite fair. Is he more likely to deal prospects than Cherington was? Sure. More likely to push for a big contract for a pitcher this offseason? Probably. But Henry and Mike Ilitch seem to be very different owners, and while the latter’s all-out win-now mandate may have motivated Dombrowski to make some of the moves he’s pushed the button on over the past few years, Henry is likely to take a more measured approach. Not that I don’t expect Dombrowski to wheel and deal, mind you: just don’t assume Bogaerts, Betts and Rodriguez will all be wearing different uniforms in six months, and stop photoshopping David Price in a Red Sox jersey.

What does this mean for the rest of the Red Sox leadership? Dombrowski has to make decisions there, too. Bob Nightengale reported that Frank Wren should be viewed as the frontrunner for the Red Sox’s GM job after Cherington declined to continue in that position. A Dombrowski/Wren combination would seem to signal a stark shift in philosophy away from the Epstein/Cherington eras. Dombrowski will also need to decide the fate of John Farrell, who recently stepped down for the remainder of the year to battle cancer but who is under contract for 2016 and has professed a desire to return.

Dustin Pedroia and David Ortiz are locks to be back with the Red Sox next year. I mention that becomes little else seems certain, and given the prospects and money Dombrowski has to work with now, a significant roster shakeup seems likely. Given the state of the Red Sox’s pitching staff, defensive alignments and two-year stretch of awfulness, perhaps it’s much needed.

Whatever Dombrowski decides to do, he had best do it quickly. As his own dismissal from the Tigers and edging out of Cherington proves, major league baseball is still often a “what have you done for me lately” world. The speed with which Dombrowski is able to rebuild the Red Sox into a perennial contender will likely decide how we remember his stint in Boston.

But regardless of what Dombrowski does, odds are, his tenure won’t be as strange as Cherington’s.