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Boston Red Sox: 3 bad strategies that stifle team’s success

Michael DeVito
Michael DeVito

Chowder and Champions

LOS ANGELES, CALIFORNIA - OCTOBER 12: Mookie Betts #50 of the Los Angeles Dodgers hits a double in the seventh inning in game two of the National League Division Series against the San Diego Padres at Dodger Stadium on October 12, 2022 in Los Angeles, California. (Photo by Ronald Martinez/Getty Images)

The Boston Red Sox are not a good baseball team and this offseason’s activity is not adding much to change that observation. They are a last-place team in the American League East deservedly so and it’s no accident. It’s due to poor strategic decision-making.

The ownership of the team presumably supports the current direction but the man in charge day-to-day is Chief Baseball Officer, Chaim Bloom. Bloom has had an up-and-down tenure in his first three years in Boston after he replaced the wildly successful Dave Dombrowski.

Those were big shoes to fill and thus far he’s nowhere close to filling them. Whether this direction and the budget were set by the absentee ownership or Bloom’s own decisions, in two of his three years at the helm he’s found his team firmly ensconced in last place in the AL East.

There have been three major areas of flawed strategic decision-making within the past five years since 2019 and Dombrowski’s firing that punctuate this precipitous fall. Let’s take a look at those mistakes.

Boston Red Sox three strategic errors that dump them into last place

First, the Red Sox since 2018 has eschewed the superstar route and sought to economize, aka go cheap, by trying to aggregate any number of mediocre players instead. It’s sort of a “sum of the parts equals the whole” theory. It can work but doesn’t very often.

Bloom got the ball rolling on this method by dealing one of baseball’s best and soon-to-be most expensive players, superstar Mookie Betts. An old saying warns, “you get what you pay for”.

They decided to trade Betts for one average major league-ready player and two prospects, a complete disaster. Only Alex Verdugo has been a starter and the two prospects, Connor Wong and Jeter Downs (DFA’d recently) have not been a factor.

He has also just lost another All-Star, Xander Bogaerts in free agency. While this space doesn’t have a problem with the player leaving, the continuation of the precedent is what’s at issue. Trade him (the last offseason was optimum) for top major league value? Fine. Replace him with another and more reasonably priced top MLB player? Fine. The Sox just let him walk. Not good.

Boston Red Sox
Former Red Sox outfielder Hunter Renfroe. (Photo by Stacy Revere/Getty Images)

Second, the Boston Red Sox overpay mediocre players

Compounding the no-stars approach, the Sox have sought to replace them with older players for the most part who can’t possibly replace the star players they send packing.

Absent a masterful implementation of this strategy in 2021 when virtually all of Bloom’s trades and signings worked, he has flopped in the player management arena.

Bloom undid two of his best moves in 2021, signing Hunter Renfroe and trading for Kyle Schwarber. He evidently couldn’t stand prosperity so he jettisoned both in the offseason. Renfroe was traded to Milwaukee in a truly bizarre deal. He re-acquired weak-hitting former Red Sox cast-off Jackie Bradley Jr. and two of the so-valued, “prospects”.

Bloom traded one, didn’t sign the other, had Bradley at his whopping $17.5M salary for 2022 (and he was DFA’d), and also signed a Tommy John surgery-recovering pitcher, James Paxton for $10M for two years. He never threw a pitch in 2022 for $6M.

Aggregate the money spent on Bradley, Paxton, and a couple of other mediocre MLB retreads, and voila, there’s the salary plus for Schwarber, who led the National League with 46 home runs, and probably Renfroe too.

Boston Red Sox
Boston Red Sox star Rafael Devers. (Photo By Winslow Townson/Getty Images)

Third, the Boston Red Sox don’t retain their best homegrown players

The Boston Red Sox drafting has been atrocious. Most of their recent best players have been international signings like Bogaerts and Rafael Devers, and a few previous good free agency signings. Developing starting pitching hasn’t happened since Jon Lester.

Bogaerts left and negotiations with Devers seem light years apart. That’s another huge strategic mistake. The model is, first you keep your very best players (signing them early is optimal), and then poach the other guy’s best free agents.

The norm now seems to be that you just let your best go, replace them with older perhaps decent players, and still wind up spending almost as much as you would have on the best.

The summary of all this is that the Boston Red Sox strategy if they even have a strategy is totally flawed on at least three major levels. There probably are others.

There is still time through trades or a signing or two to crawl back for 2023, but the clock is ticking and the best free agents are signed. Maybe trades will help. We’ll see.

What do you think are the reasons the Red Sox have fallen so far so fast? We’d like to hear.

Michael DeVito

Michael DeVito

Michael is a long-time New England Patriots fan. He closely follows the Patriots' offseason team-building activities, including the Patriots' Draft, Free Agency, and Undrafted Free Agency. Michael also follows all Boston sports. He is also a big fan of the Chelsea Football Club in the English Premier League.