Here's the thing about Dave Dombrowski's "worst" deals -- they almost always landed impact players.
When he overpaid for closer Craig Kimbrel, in his first major acquisition as Red Sox president of baseball operations, he still landed an All-Star. When he took the David Price bidding into the stratosphere in what became the highest contract ever given to a pitcher, he still landed the de facto 2018 postseason MVP. When he surrendered promising left-hander Jalen Beeks to the Rays, he still landed eventual playoff hero Nathan Eovaldi.
But those deals still took a toll on the long-term health of the organization, and it's worth exploring how they came to be viewed by ownership as signals that Dombrowski wasn't the right man to lead the baseball operation moving forward, which is why he was fired on Sunday night.
Start with Kimbrel. Dombrowski acquired the All-Star closer from the Padres on Nov. 13, 2015, by making what became his signature -- the offer you can't refuse. The trade created a ripple of uneasiness across a front office that had grown accustomed to the hoarding of prospects by predecessor Ben Cherington, even as it recognized the need to ease up on the reins.
At issue: the centerpieces of the trade -- outfielder Manuel Margot and infielder Javier Guerra -- represented a fair price on their own to acquire the disgruntled closer, who hadn't thrived in San Diego after five years of dominance in Atlanta. Each was a consensus top-60 prospect, with Baseball Prospectus ranking Margot 14th following the 2015 season.
Dombrowski is a man of action, however, and he wanted the deal done, so he sweetened the pot with left-hander Logan Allen, a teenager who had just posted a 1.11 ERA in his pro debut while walking only one batter in 24.1 innings.
While Kimbrel certainly produced in Boston, making three All-Star teams and saving more than 100 games, the loss of Allen proved costly this July when the Indians made him a central figure in the three-way trade that sent right-hander Trevor Bauer to Cincinnati, top prospect Taylor Trammell to the Padres, and Allen and slugger Franmil Reyes to the Tribe.
Boston Red Sox
Allen debuted this season at 22 and is exactly the kind of cost-controlled piece the Red Sox could use to augment a rotation that's underperforming and overpaid.
Speaking of the rotation, Dombrowski has committed more than $400 million to three giant question marks -- Price, Chris Sale, and Eovaldi. When the Red Sox signed Price for a record $217 million a month after acquiring Kimbrel, they didn't just surpass the next-highest offer, they obliterated it. The runner-up Cardinals reportedly offered Price a seven-year deal in the $175 million range. The Red Sox blew that number out of the water to overcome whatever misgivings Price may have harbored about pitching in Boston, which probably should've been a red flag. As the Globe's Alex Speier noted, they effectively bid against themselves. Now his contract looks unmovable.
Then there's Eovaldi. This was an under-the-radar moment, but many in the organization felt he could be acquired without surrendering Beeks, a hard-throwing left-hander who had impressed in an emergency start against Team USA before the 2017 World Baseball Classic, when he struck out Christian Yelich and Adam Jones in two scoreless innings.
Beeks had a number of advocates on the player development side who recognized his potential to develop into a big league starter, especially after he overhauled his arsenal to feature a 95 mph four-seam fastball and cutter.
It's easy to look at that deal and say, "Eovaldi was instrumental in winning a World Series. Who cares that you gave up Jalen Beeks?" But what if the Red Sox could've acquired Eovaldi for a lesser prospect -- and with Eovaldi coming off yet another arm surgery, his market wasn't exactly robust -- and kept Beeks?
He'd be another depth option in an organization that badly needs it. Instead, he has emerged as a key multi-inning arm in Kevin Cash's bullpen, with an 11-3 record since arriving in Tampa.
The same can be said of Giants right-hander Shaun Anderson, a 2016 third-round pick shipped to San Francisco in 2017 for Eduardo Nunez. Anderson has made 16 starts in the big leagues (albeit with a 5.22 ERA) and owns a higher ceiling than the pitchers the Red Sox were forced to throw in the 4-5 spots of the rotation this season.
Meanwhile, how much could the bullpen use someone like Ty Buttrey? The 6-foot-6 right-hander had some command issues early in his minor league career, but since going to the Angels last July for second baseman Ian Kinsler, has averaged nearly 11 strikeouts per nine innings while posting a 3.90 ERA. That's a solid setup man in exchange for a second-base rental.
In each case, there was apprehension within the organization that Dombrowski was overpaying. That's tolerable when the farm system is loaded, but it's not sustainable, which is why the Red Sox suddenly find themselves in the market for a new GM.
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