Insider Warns Red Sox Failure To Keep Playoff Legend In Boston Was ‘Obvious’ Mistake

At this point, the 2021 Major League Baseball playoffs feel like ancient history.

The Boston Red Sox haven’t been in the postseason for the last three years, and that isn’t supposed to be the norm for such a storied franchise. They advanced all the way to the American League Championship Series that October, leaving few thinking it would be their last trip to the dance for a while.

So much has changed in Boston since 2021 that the playoffs are now something of an exhibition of former Red Sox players. Gone are stars of that team like Xander Bogaerts, J.D. Martinez, and Kyle Schwarber, and that’s not even to mention former Boston superstar Mookie Betts, who was gone even sooner.

Schwarber had the shortest tenure with the Red Sox of all the names above, yet his loss may be the most painful during postseason baseball. He’s become an October legend through the years, and he’s already flexed his playoff prowess through two games in 2024.

On Sunday, MassLive insider Sean McAdam lambasted the Red Sox for letting Schwarber walk after that 2021 campaign, when he had one of the best stretches of his career in Boston.

“By now, it’s obvious that the Red Sox made a mistake in not retaining Kyle Schwarber after the 2021 season,” McAdam said.

“At the time, Schwarber was somewhat redundant because of fellow DH J.D. Martinez. But the Sox should have eaten the necessary money needed to trade Martinez and kept Schwarber, who has averaged 44 homers over the last three seasons with the Phillies… He’s also established himself as a dynamic postseason performer, with a .987 OPS.”

Schwarber only played 41 regular-season games for the Red Sox, but his .957 OPS in Boston nevertheless ranks the highest of any single-team mark of the superstar’s career. He also hit three massive home runs for the Red Sox in the playoffs, though he did go 3-for25 in the ALCS against the Houston Astros.

With a leadoff missile against the New York Mets on Saturday, Schwarber moved to fourth all-time on the postseason home run leaderboard. He has hit 21 longballs in his playoff career, eight behind Red Sox icon Manny Ramirez for the all-time lead.

Seeing any former player succeed for another organization will always carry mixed emotions, but there’s a little extra sting when it’s a player with a storied track record such as Schwarber. And it never sounded as though Boston even attempted to pursue the slugger, which makes the loss hurt all the more.

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