The question was echoed by others throughout the industry over the subsequent months. Those who asked the question never came up with the simple answer – “Yes” – that would have suggested a contract extension for Dombrowski. With Dombrowski approaching the final year of his contract in an offseason that promises to be among the most challenging faced by the Red Sox in years, the groundwork was laid for Dombrowski’s departure before a potentially tumultuous hot stove season.

The question was posed by a member of the Red Sox organization about president of baseball operations Dave Dombrowski in May. It reflected the idea that the team was preparing to embark upon a very different future course than the one it had navigated – very successfully, including through a championship and a record-setting number of wins in 2018 – over the previous four years under Dombrowski.

On one hand, the after-midnight firing came as something of a shock, mostly for the suddenness of its timing. On the other hand, there was a sense of inevitability in some corners, that the Sox were entering a new roster-building phase for which Dombrowski was no longer the ideal fit that he’d been when hired.


Dombrowski came to the Red Sox amidst a two-year streak of decisions on the big league roster that had gone awry in Boston. In August 2015, Hanley Ramirez, Pablo Sandoval, Rick Porcello, Allen Craig, and Joe Kelly had all offered terribly disappointing returns. The Sox, who were brimming with young talent that was gaining a foothold in the big leagues and more in the minors, needed someone to make the right decisions to add big league talent to supplement that young core.

Dombrowski represented the perfect fit, to the point that the Sox made a shocking, in-game announcement on Aug. 18, 2015, that Dombrowski was in as president of baseball operations and Ben Cherington was out as general manager. Through 2018, Dombrowski’s decisions methodically and perfectly supplemented the group he inherited.


His big-ticket additions such as David Price, Craig Kimbrel, Chris Sale, and J.D. Martinez all came as advertised. He also shrewdly supplemented his roster with in-season moves, with deals for Brad Ziegler in 2016, Eduardo Nunez and Addison Reed in 2017, and Steve Pearce and Nate Eovaldi in 2018 making the team appreciably better. Still, there were concerns about how Dombrowski got deals done, sometimes at the expense of the long-term.

In the Kimbrel deal, members of the organization felt that an offer headlined by two top-100 prospects – Manny Margot and Javier Guerra – would trump anything else the Padres would encounter. In the interests of securing a deal, however, Dombrowski nonetheless proved willing to include lefthander Logan Allen in the trade. This summer, Allen emerged as a big league starter. The lefthander played a significant role in the three-team deal with San Diego, Cleveland, and Cincinnati that sent Trevor Bauer to the Reds and prospect Taylor Trammell to the Padres.

In the Price negotiations, Dombrowski and the Sox knowingly bid against themselves in order to close a deal before the winter meetings.

Dombrowski did prove capable of drawing a line in some high-level negotiations. After the 2015 season, he helped steer the organization toward the acquisition of an ace (Price) rather than a deal that would sacrifice emerging core assets such as Mookie Betts or Xander Bogaerts.


When the White Sox asked for Rafael Devers in addition to Yoan Moncada and Michael Kopech in the deal for Sale, the Red Sox drew a line – ultimately resulting in the retention of a player who has emerged as a star. He protected Andrew Benintendi and Devers – players who proved capable of making rapid transitions to impact status in the big leagues. After the Sale deal, he avoided any deals that involved the best Red Sox prospects, often outlining the team’s need to refill its system.

That said, even as he’s overseen the start of a repopulating of the team’s prospect pool, Dombrowski showed a propensity to double-down in costly fashion on bets that had paid off once. He re-signed Nunez despite medical questions at the start of 2018 – a move that ultimately not only helped push the team over the third and highest luxury tax threshold in that championship season (with consequent draft pick penalties), but that also offered little return and that constrained the team’s 2019 payroll. With more than $20 million in payroll flexibility this winter, he re-signed other players who’d been acquired on efficient deals – Pearce and Eovaldi – to contracts that played a significant role in the team’s offseason.

In re-signing Eovaldi and then reaching a long-term deal with Chris Sale, Dombrowski put the Sox in a position where – based on their payroll projections and a significant desire to get under the luxury tax threshold sometime in the next two years to reset the penalty structure – they’ll likely end up parting with J.D. Martinez, Mookie Betts, or possibly even both this winter.


That prospect loomed large over Dombrowski’s future in the organization. The Red Sox went through a painful building period under Cherington in 2014-15 in which they hoarded prospects while enduring two straight last-place finishes. Still, the course charted by Cherington was viewed as the right one at the time. The team went through a wildly successful win-now period from 2015-18; Dombrowski was the right steward of that period.

Now, the mandate is different. The organization’s success in the coming years rests on the ability to operate creatively. The Red Sox are attempting to thread the needle, parting ways with elite players to maintain what they consider a manageable and sustainable payroll as well as championship aspirations.

At the trade deadline this year, Cleveland dealt a star – Trevor Bauer – who was one and a half years from free agency in a fashion that may well have augmented both its short- and long-term hopes.

The Diamondbacks, under the direction of former Red Sox GM Mike Hazen, dealt Zack Greinke to create long-term payroll flexibility in one deal while landing emerging frontline pitcher Zac Gallen in another, deals that improved Arizona’s long-term outlook through the addition of payroll flexibility and prospects while also setting the stage for a surge that has the D-backs competing for a playoff spot. Those deals came after an offseason trade of franchise cornerstone Paul Goldschmidt for two players – catcher Carson Kelly and (currently injured) starter Luke Weaver – who have likewise been key contributors this year.


Dombrowski did that once in Detroit after the 2009 season, when he landed Max Scherzer in a three-team deal that saw Detroit part with Curtis Granderson. But when potentially given an opportunity this summer to explore the value of multiple members of their big league roster and to try to navigate that same short-term/long-term balancing act of smaller-market teams such as Arizona and Cleveland, Dombrowski remained committed to the roster with which he’d won in 2018.

The decision to do so was understandable and certainly justifiable. But inevitably, key contributors to that championship season – beyond relievers Craig Kimbrel and Joe Kelly – were going to have to go.

If the Red Sox didn’t know if Dombrowski was the right person to steward that process by now, then it was a question of when, not if, the conclusion of his enormously successful run in Boston would arrive, particularly in an era where analytics (a field in which Dombrowski became conversant with the Red Sox, but always as an acquired second or third language) will play a growing role in decision-making.

A potential reckoning seemed to loom this offseason – both for the president of baseball operations and for the roster. That reckoning arrived earlier than expected for Dombrowski, something that will allow the Red Sox to get an earlier start on finding the person who will be in charge of a pivotal offseason that will shape the Sox into the next decade.

Alex Speier can be reached at alex.speier@globe.com. Follow him on twitter at @alexspeier.