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Dave Dombrowski Did Everything He Was Supposed to in Boston. The Red Sox Fired Him Anyway.

The firing of the president of the World Series titleholders proves that high payrolls and win-now aggression are tolerated only until the winning stops

Getty Images/Ringer illustration

Here is everything the Red Sox accomplished in four seasons with Dave Dombrowski in charge of baseball operations:

  • Won a World Series
  • Won three consecutive division titles for the first time in franchise history
  • Won 108 games in a season—the most in franchise history, and one of the highest totals ever for a World Series winner
  • Won more combined regular-season games than any team other than the Astros and Dodgers
  • Won an MVP, via Mookie Betts, and a Cy Young, via Rick Porcello

Here is everything Dombrowski didn’t do, which apparently was enough to warrant his firing, which the Red Sox announced late Sunday night after a 10-5 Yankees win at Fenway Park:

  • Make the playoffs every year

So that was that. Dombrowski is gone, just 11 months after his team clinched a World Series title, and Boston will conduct a search for his long-term replacement, with a group of front office folks operating jointly at the top of the Red Sox hierarchy in the interim. It was quite the late-night news dump, after a 2-4 week dropped Boston a likely insurmountable eight games back of a playoff spot. Boston didn’t just fail to repeat as champion; it raised serious, wide-spanning questions about both the organization’s future and the sport’s changing front office calculus as a whole.

Dombrowski joined the Red Sox in advance of the 2016 season, after more than a decade as the GM in Detroit, and before that time in charge in Florida and Montreal, and he immediately made his mark on a roster that brimmed with talent but couldn’t quite put all the pieces together. Early in his first offseason in Boston, he traded a package of four young players for closer Craig Kimbrel and signed David Price to a seven-year, $217 million free-agent deal—the largest-ever contract for a pitcher. It was Dombrowski in a nutshell, as the longtime executive has always displayed an aggressive, risk-taking approach to try to win. He did so in Boston for three years, but one lost year evidently outweighed the larger number.

That’s an oversimplification of the situation, of course, as is the cheeky lone bullet point up above. Dombrowski’s club won’t just miss the playoffs this season; it will miss the playoffs while running the sport’s highest payroll and failing to complement its MLB core with a robust farm system that can give Boston, à la the Dodgers, a sort of perpetual contender for years to come.

Both those criticisms are true in a vacuum, though a bit misguided in context. On the financial side, Boston also had the sport’s highest payroll last season, but it won the championship then, so it was OK. Their nine-figure signees under Dombrowski—J.D. Martinez and Price—played crucial roles on a championship team, and even though the long-term deals offered to pitchers Chris Sale and Nathan Eovaldi look worse now, after a season full of injuries, it’s too early to conclude that they will prove disasters over their entire span. Sale, after all, was still one of the majors’ best pitchers when healthy this season, and it’s hard to blame Dombrowski for a complacent post-title offseason when that’s an established trend in the sport.

Nor has his free spending hampered the roster’s long-term viability. A quartet of Red Sox who made a combined $37.45 million this season—Rick Porcello, Mitch Moreland, Steve Pearce, and Brock Holt—will be free agents this winter, and Boston will also shed eight figures in annual payments to Pablo Sandoval. Sure, the club’s future finances are less flexible than those of teams without any long-term, high-cost commitments, but even within a prescribed budget, Boston can put together a winning roster. And that assumption is also worth questioning: Remember, baseball doesn’t have a salary cap, just the over-frightening specter of a rather harmless luxury tax that has nevertheless given financial behemoths in the Bronx and Los Angeles an excuse to cut costs. (Boston owner John Henry, it’s worth noting, is worth an estimated $2 billion to $3 billion—enough zeroes to qualify Henry for Forbes’ list of the country’s wealthiest sports owners last fall.)

As befits his reputation, Dombrowski has also overseen the depletion of Boston’s farm system, which now ranks as the worst in baseball, per FanGraphs, with only one prospect sneaking into the top 100 at 96th overall. Part of this drop is the result of a natural competitive cycle, as the system’s top prospects matriculated to the majors and helped the Red Sox win a championship; the Astros, Yankees, and Cubs also rank in the bottom half of farm systems, even if their outlook is better than Boston’s.

Part of it is also the result of a few poor cycles of drafting and development. Dombrowski traded some top prospects away, too—but all in the service of improvements to the MLB roster, theoretically the entire point of running a team. Looking at Dombrowski’s individual prospect trades, it’s hard to fault him for any one of them. He traded only six players who ever ranked among Boston’s top 10 prospects, per Baseball America, and half of those were for Sale, who has turned into the American League’s best pitcher since he landed in Boston. Here’s how those six have fared since being traded:

  • Yoán Moncada (White Sox, for Sale): has developed into a solid regular and possible future All-Star, worth 3.2 WAR this year
  • Michael Kopech (for Sale): missed all of 2019 due to Tommy John surgery; still a highly regarded prospect
  • Luis Alexander Basabe (for Sale): had a .660 OPS this year in Double-A, where he struck out in nearly 30 percent of his plate appearances
  • Manny Margot (Padres, for Kimbrel): has turned into a poor man’s Jackie Bradley Jr., with a career OPS below .700 despite strong defense in center field
  • Anderson Espinoza (Padres, for Drew Pomeranz): hasn’t pitched in the regular season since 2016 because of two Tommy John surgeries
  • Mauricio Dubon (Brewers, for Tyler Thornburg): was sufficiently lightly regarded that he went from Milwaukee to San Francisco at this year’s deadline for a rental reliever, which makes sense for a player who debuted in the majors just two weeks before turning 25

Aside from Moncada—who, again, brought back Sale, the best Boston pitcher since Pedro Martínez—none of these players should keep Boston executives up at night. In this respect, Dombrowski’s Boston tenure reflects his prior stint in Detroit, where he developed the same reputation. Even as he and late owner Mike Ilitch raced to pursue a title, though, the worst trade he made has probably turned out to be losing Eugenio Suárez, a nonprospect whose absence nobody lamented at the time.

Dombrowski didn’t win every transaction in Boston, of course; his Thornburg trade proved to be a debacle, costing Boston not just Dubon but useful infielder Travis Shaw as well. But Dombrowski won many more trades than he lost. He turned a 10th-round draft pick with middling minor league numbers, for instance, into Steve Pearce, who won the World Series MVP, and he basically stole Kimbrel, who across his three seasons in Boston ranked second among qualified relievers in strikeout percentage, 10th in park-adjusted ERA, sixth in park-adjusted FIP, second in win probability added, and third in saves. (After Margot, the second-best prospect in that trade, shortstop Javy Guerra, converted to a reliever this season because he couldn’t hit enough to stick in a lineup.)

Instead of an indictment of his individual decisions as an executive, Dombrowski’s firing seems to reflect a broader truth about the state of baseball. Successful general managers and presidents of baseball operations have reined in spending to their owners’ delight and generally prioritized an organizational strategy that values the dream of a winning team in the future more than the reality of a winning team in the present. The takeaway seems to be that high payrolls and win-now aggression are not encouraged, but tolerated—until the winning stops, even for a moment, at which point those factors are sufficient cause for a complete front office overhaul.

Other World Series winners of recent vintage have passed on lessons to the rest of the sport: the Royals, the elevated postseason value of a shutdown bullpen; the Cubs and Astros, the viability of a tanking and rebuilding approach. But few teams, if any, have learned the lesson of Boston’s 2018 title: spend and spend big, in money and prospects, because players like Sale and Kimbrel and Price and Martinez don’t come cheap, but they might just help a franchise to its best season ever.

Boston has been in this situation before, and recently. Less than two years after winning the 2013 title, the Sox replaced GM Ben Cherington atop the org chart in August 2015. At least with that move, though, there were greater on-field precipitators. Cherington had built a World Series winner, but the Red Sox were en route to their third last-place finish in four seasons with him in charge. Cherington’s dual signings of Sandoval and Hanley Ramírez look far more foolish than any move Dombrowski made at the helm. A comparison between the two executives’ records shows that their removals were of a different kind.

A Tale of Two Red Sox Leaders

Statistic Cherington Dombrowski
Statistic Cherington Dombrowski
Seasons 4 4
Championships 1 1
Winning Seasons 1 4
Wins 315 370
Losses 333 259
Winning Percentage 0.486 0.588
First-Place Finishes 1 3
Last-Place Finishes 3 0

Cherington deserves ample credit for Boston’s 2018 title, too, as the player development system he oversaw helped turn a host of young players—Betts, Xander Bogaerts, Rafael Devers, and more—into an eventual championship core. His Boston tenure looks better for what came immediately after.

Boston might find itself in the opposite situation with Dombrowski, as the Sox stare down an uncertain future. They have little internal help ascending the minor league ladder soon, and Sunday’s news—along with the team’s lack of spending last winter, either to retain Kimbrel or install a reliable replacement at closer—means it’s unclear how much ownership will commit financially to roster upgrades with Dombrowski-era contracts still on the books. Most notably, Betts will be a free agent after next season and should command a sizable contract, near or beyond the benchmarks set this winter by Bryce Harper and Manny Machado.

The irony is that in a Dombrowski replacement, the club should be looking for the kind of executive who can guide a team with a strong core over the competitive finish line. Ideally, the next Red Sox GM would have a track record of success with this kind of roster, maybe even championship experience, and a keen understanding of how both large- and small-scale transactions can complement each other in building a title winner. The Red Sox need a proven World Series architect. I wonder if anyone who fits that description might now be available.