Even though it’s been four years, it’s still pretty hard to stomach that Mookie Betts will someday go into Cooperstown wearing a Los Angeles Dodgers cap instead of a Boston Red Sox one.
Since 2020, Red Sox fans have been told that even if ownership could pay Betts a $300 million contract, the team had no hope of contention because all the good minor leaguers were gone.
If Craig Breslow wants to have a successful tenure as chief baseball officer, he needs to recognize that trading away prospects was never the issue.
For the past six years, ownership has told fans that Dave Dombrowski — the team’s president of baseball operations from 2015 until his unceremonious firing in September 2019 — spent up every last resource the team had in the farm system to trade for players who fell apart after the 2018 World Series.
Yes, Boston’s three most significant pitcher acquisitions were given ungodly amounts of money but then played small amounts of baseball. After 2018, David Price, Nathan Eovaldi and Chris Sale were paid a combined $231.5 million — not including the portion of Price’s contract the Red Sox paid after he was traded to the Dodgers — for just 162 starts or around $1.4 million per start.
But, saying that the Red Sox also spent significant prospect capital to acquire Eovaldi, Sale and other pieces of the 2018 core would be incorrect.
In his time with the Red Sox, Dombrowski only made three significant trades using prospects. Those trades acquired Sale, Eovaldi and closer Craig Kimbrel. The three gave the Red Sox 31.2 wins above replacement, or WAR, in their careers in Boston.
The teams those players came from received comparatively little in return: a combined 25.1 WAR over those Sox prospects’ careers with their respective teams.
Yoan Moncada has the best WAR, 14.7, for his team, the Chicago White Sox, after he was traded alongside Michael Kopech in exchange for Sale. But Moncada has never been an All-Star nor won any awards and has only appeared in the playoffs once.
Overall, Dombrowski made few trades, and when he did, the outcome heavily favored the Red Sox.
His main mistake was dishing out exuberant contracts to injury-prone pitchers like Sale and Price. Keep in mind, though, that dollar amounts of that magnitude need to be signed off on by John Henry.
It’s really hard, if not impossible, to buy into the idea that Dombrowski ran amok with the baseball operation, spending way too much money, without anyone in ownership ever noticing.
You may be asking, ‘Well, if Dombrowski didn’t trade away all the prospects, how come the Red Sox farm system plummeted in rankings under his watch?’
The answer is pretty simple. Good prospects, like Betts and Rafael Devers, were drafted when the team wasn’t winning and had high picks in the MLB Draft. These players then graduated to the major leagues, which led to winning, making it harder for the Sox to draft top-level prospects.
Want to hear something even more shocking? Some of the best young players on the current major league roster, like Jarren Duran and Triston Casas, were, in fact, drafted by Dombrowski.
The Dombrowski approach worked. Similar methods have always worked in Boston and across MLB. Even the Red Sox admit this.
Team president Sam Kennedy told WEEI earlier this year: “The philosophy here for 23 years, the strategy, is to build around a core group of young, homegrown players and add free agents at a period of time where you think you’re ready to take that next step and win a World Series.”
But, when the Red Sox fired Dombrowski in 2019 and hired Chaim Bloom, their strategy shifted towards a Tampa Bay Rays model. It shifted so far that the team needed to make a change at the executive level once again, bringing in Breslow.
Bloom gained a reputation for being a far more methodical and measured executive, someone who, to a fault, wanted to win every trade. But when you compare his moves to that of Dombrowski’s, it’s hard to see how he gained it.
In his four years with the Red Sox, Bloom made 16 trades — that’s excluding smaller trades that involved minor league swaps.
His masterpiece was trading Christian Vazquez to Houston, who played as their backup catcher for one playoff run, in exchange for an already Gold Glove outfielder in Wilyer Abreu and a solid bench utility player in Enmanuel Valdez.
His most infamous deal, trading away Betts to the Dodgers, is by far his worst. It’s hard to imagine how that trade, which has given LA 28.8 in WAR and Boston 11.6 so far, could have gone any more poorly.
Overall, Bloom’s deals have proven to be blunders. The Sox gave up 40 WAR in return for 28.4, but, to be fair, it’s probably still early for his legacy to be thoroughly evaluated.
The quality of Boston’s farm system at this moment has little to do with shrewd maneuvering by Bloom on the trade front; it has everything to do with a poor major league product corresponding to higher draft positions and better draft picks.
Now, we turn to Breslow, who has inherited a top-five farm system in MLB that is fully loaded with potential major-league talent. The question is, what will he do with it? Or maybe a better question: what will ownership allow him to do?
Since Henry and his ownership group bought the team in 2002, most Red Sox executives have been empowered to trade from the existing prospect pool to acquire top-tier talent from around the league. But, seemingly, not Bloom.
Breslow is armed with a war chest that is arguably better than what Dombrowski used to complement the 2018 World Series team.
He could skim off the middle and lower tiers of the team’s farm system, to trade for controllable players from other teams, and still have players left over — like some combination of the Kyle Teel, Roman Anthony, Marcelo Mayer, Kristian Campbell group — who can become everyday big-leaguers.
The Sox have never been afraid of trading away prospects, and there’s no reason to start now — worrying about keeping a farm system ranking intact will not improve the major league product and it will not win championships. It’ll only improve the product at Woo Sox games.
In the next few weeks and months, we’ll find out what path Breslow takes and just how bold he is willing to get.