In the end, Yoan Moncada is gone from the Red Sox organization for the same reason that Anderson Espinoza and Ben Cherington are no longer here. The same reason, in fact, that Terry Francona and Theo Epstein are employed elsewhere these days.
This is the dark side of playing in Title Town. As Seth Mnookin so brilliantly documented a decade ago in his book Feeding the Monster, the Red Sox are an organization forever torn between trying to compete for championships today and developing a foundation for tomorrow. And with distressing regularity of late, it is today that has taken priority.
Did the 2011 Sox collapse in historic fashion at the end of the season? Goodbye Tito. Was the team’s next wave of young stars late to develop following the 2013 championship? Thanks for the memories, Ben.
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In October, after the Cubs—only recently one of the very worst clubs in baseball—at last won the World Series, Epstein was heralded as a baseball genius, a sparkling candidate for induction, some day, into the Hall of Fame. This adulation was right and just, of course, but make no mistake: What Theo accomplished in Chicago he simply could not have done during his time in Boston. And the reason for that is the same reason that the Red Sox just traded one of their most exciting position prospects in memory, just months after dealing away their most promising pitching prospect in a generation: In Boston, winning now is what counts.
How, in contrast, did Theo build a World Series champion in Chicago? It’s true that, just as Theo’s Red Sox teams had done, the Cubs scouted effectively, drafted shrewdly, and traded wisely. But the Cubs were also willing to lose in the short term as part of a strategy to win in the future. In Theo’s first year, 2012, the Cubs lost 101 games. In 2013, it was 96 games. In 2014, 89 games. Along the way, nobody panicked. No one fretted. By 2015, the team was winning 97 games. The very next season, they were champions.
This was the strategy that Theo wanted to follow in Boston, too: Compete for titles in eight out of every ten years. Use the other two years to take a step back and reload for the next run. That, as Cherington can attest, is unacceptable in Boston.
It is because Boston must compete—or at least present the illusion of competing—every year that the Red Sox could not wait to see what they had in Moncada, a switch-hitting, explosively talented dynamo with a performance ceiling widely understood to be that of a league MVP—a superstar. Moncada can hit, run, throw, and hit for power. In fairness, Moncada’s performance floor is considerably lower than that of a superstar. He is generally considered a below-average infielder, he has looked dreadful at times while batting from the right side of the plate, and he has shown an alarming propensity to strike out—he went down on strikes in nearly a third of his at-bats last year in AA Portland. Still, Moncada is just 21, and his overall performance last season was so dominant that the Red Sox, ill-advisedly it turned out, promoted him directly from Portland to Boston at the end of the year.
Whether because of concerns related to that rushed stint in the majors, or—more likely—because of the caliber of player Red Sox VP Dave Dombrowski was able to get in return for him, Moncada was used as the centerpiece in a deal to acquire the star pitcher Chris Sale from the Chicago White Sox. It was the kind of transaction that Sox fans have gotten used to since Dombrowski was hired near the end of the 2015 season. Dombrowski brought with him a reputation for a win-now approach, and since taking over, he has not disappointed. He has stripped a farm system widely acknowledged as one of the very best in baseball and sold the pieces off for major league players who can help the Red Sox win today. Once overflowing with talent, the Red Sox minor league affiliates are now all but barren.
It is important to note here that Dombrowski is on the path to executing his particular strategy for winning a championship as effectively as Theo did his. Sale is a terrific pitcher who is young, affordable, and under team control for three seasons. In other words, he is precisely the kind of player that top prospects (the promising pitcher Michael Kopech and two other minor leaguers were also sent to Chicago) should be used to land. Dombrowski has likewise used minor leaguers in good trades that brought to Boston the fine closer Craig Kimbrel and, also yesterday, the reliever Tyler Thornburg. The trade last year of Espinoza, the electrifying pitching prospect, to San Diego in exchange for the starting pitcher Drew Pomeranz was, however, less successful. Like Moncada, Espinoza, who won’t turn 19 until March, has the potential to be a superstar. He’s a long way from the majors, but it was hard not to be disappointed with the return in that deal, especially when Pomeranz pitched much less effectively with the Red Sox than he did with the Padres.
The Espinoza deal notwithstanding, it is hard to quibble with the specifics of the trades that Dombrowski has made with the team’s prospects. He has generally gotten back talented young major leaguers with multiple years of Red Sox control. With Sale added to the team’s already excellent starting rotation, the improvements to the bullpen, and the core of terrific young players entering their prime, the Red Sox are positioned to contend for championships for at least the next three years. When it comes to winning today, that is some fine work by Dombrowski. But it may also prove shortsighted.
Under Theo and Cherington, the “Red Sox Way” was to build an organization capable of competing over the long term. The best of the young players in the minors were seen not as redundancies, and not primarily as trade chips, but as replacements for aging stars who signed big contracts other teams foolish enough to pay for past performance. Dombrowski still has a star-caliber third basemen in the minors in Rafael Devers, and he still has the recently drafted pitcher Jason Groome, who has a potential top-of-the-rotation arm. But in terms of excellence, that is pretty much it in the Sox’ minor league system. So where will the next wave of great young players come from when the current crop moves on in a few years? That’s unknown.
What makes that uncertainty so troubling is that there used to be a set of rules governing the stocking of the minor leagues that Theo and Cherington used to build the farm system that produced the current championship-level team. Unfortunately, many of those rules have been changed. No longer can the Sox and other big-market teams spend as much as they want on the major league draft, a change that has discouraged top players from letting it be known that they will not sign with smaller-market teams, effectively forcing those teams not to draft them. Likewise, recent changes to the Collective Bargaining Agreement have made it so that the Red Sox can no longer spend freely on international free agents—the players from baseball hotbeds such as the Domincan Republic, Cuba and Venezuela that are not subject to the draft. Players, come to think of it, like Yoan Moncada and Anderson Espinoza.
Moncada and Espinoza would have been perfect candidates to extend the Red Sox championship window. But like so many of the team’s other prospects, they are gone now. When the glory of today’s victories fades, we may find ourselves mourning tomorrow.
John Wolfson spends a lot of time thinking about the Boston Red Sox, politics, current events, and poker. He is the editor of Tufts Magazine and the former editor of Boston magazine. His writing has appeared in publications including The New Yorker, The Atlantic, and The New York Times.