Celebrate the 32nd anniversary of Hall of Shame Red Sox trade

On this day in 1990: the Red Sox trade Jeff Bagwell to the Astros for Larry Anderson

Chaim Bloom has come under fire for most of his trades since taking over as Chief Baseball Officer of the Boston Red Sox in late 2019.

The Mookie Betts trade is the most obvious (though it was essentially decided before Bloom arrived); the Jackie Bradley Jr.-Hunter Renfroe deal is the most recent.

But exactly 32 years ago, the Sox made what turned out to be one of the worst trades in baseball history, and maybe, it will put current issues in perspective, because you might not endorse or like all of Bloom’s deals, but rest assured, it’s almost impossible to make a decision as dumb as this one.

In August 1990, the Sox were 71 years into their World Series drought and pushing to make the postseason for the third time in five years. The only problem was, they had one of the worst bullpens in the league. It seems some things never change.

At the end of August, the Sox wanted Houston Astros reliever Larry Anderson and his magnificent slider, and the Astros wanted a prospect named Scott Cooper. Sox GM Lou Gorman refused to give them Cooper but agreed to part with Jeff Bagwell (yes, that Jeff Bagwell) instead.

Gorman had already traded a pair of young prospects named Brady Anderson and Curt Schilling to the Baltimore Orioles for Mike Boddicker in 1988. This deal would turn out much worse.

At the time, Bagwell was one of the Sox’ top prospects, but they already had Wade Boggs at third base (Bagwell was drafted in the 4th round as a 3B) and Carlos Quintana at first, as well as future star Mo Vaughn coming up in the minors at the same time.

In retrospect, the smart move would’ve been to give Cooper to the Astros, develop Bagwell as the first baseman, and Vaughn as the everyday DH. But in the pre-Moneyball era, Bagwell’s ability to draw walks and post a high OBP weren’t valued the way they would be now. The Astros were actually hesitant to take him, until their scout, a Massachusetts native by the name of Stan Benjamin, informed them that the reason the young prospect wasn’t hitting for power was that he was playing in New Britain’s Beehive Field, a famously unfriendly park for hitters.

In an ironic twist, the player Benjamin used to convince the Astros to give Bagwell a shot would turn out to be a fitting comparison, just not in the way he expected:

“Babe Ruth couldn’t hit home runs in that ballpark.”

Benjamin was right on the money; over 15 seasons, Bagwell hit 449 home runs.

While Anderson lived up to his reputation in the regular season, he struggled on the mound in October, and the Oakland A’s swept the Sox out of the ALCS. Regardless, the short-term rental wasn’t worth sacrificing an entire Hall of Fame career, which is what Bagwell ultimately had. He won Rookie of the Year the following season, and over a 15-year career, all in an Astros uniform, he went to four All-Star Games, won three Silver Slugger awards, a Gold Glove, and 1994 NL MVP (the Astros used to be in the NL). Four times, he played all 162 games; in all but three seasons, he played at least 142.

To make matters worse, due to team owners’ colluding against free agents for years, the Sox ended up losing Anderson that offseason. He and over a dozen others who’d been free agents during the 1987-88 offseason were given the opportunity to be ‘new-look free agents,’ essentially a chance to seek more lucrative contracts on the open market after owners had conspired to keep free-agent salaries low. Anderson left the Sox and signed a two-year deal with the San Diego Padres.

Days after the trade, Cooper made a brief MLB debut, coming in to pinch-hit for Quintana. He ended up playing parts of the following four seasons for the Sox and was an All-Star in 1993 and 94. After playing one season apiece for the St. Louis Cardinals, Japan’s Seibu Lions, and Kansas City Royals, Cooper retired after being released from a minor-league deal with the Texas Rangers in 1998. He never came close to measuring up to the player the Sox gave away instead of him, though both hit for the cycle during their respective careers.

In 2001, ESPN sorted through approximately 2,000 letters and assembled the list of readers’ choices for the most lopsided trades in sports history. Coming in at No. 1, with 292 submissions, was the Sox’ decision to sell Babe Ruth to the Yankees. The Bagwell trade was a close second, with 267 votes, an inadvertent full-circle moment for Benjamin.

How different would the Red Sox of the 1990s look with Bagwell? We’ll never know. Do they reverse the Curse years earlier? The implications and ripple effect (A-Rod, David Ortiz, etc) would be massive.

Regardless, this mistake should serve as a reminder that there have been awful trades before Bloom (Babe Ruth comes to mind), and there will inevitably be more when he’s gone. It’s somehow both comforting and infuriating, just like baseball.