Red Sox Preseason Trade Was Worst Move Since Babe Ruth, Says Insider

Not exactly a glowing review, and understandably so...
Sep 20, 2019; St. Petersburg, FL, USA; A detail view of Boston Red Sox hats and gloves at Tropicana Field. Mandatory Credit: Kim Klement-Imagn Images
Sep 20, 2019; St. Petersburg, FL, USA; A detail view of Boston Red Sox hats and gloves at Tropicana Field. Mandatory Credit: Kim Klement-Imagn Images / Kim Klement-Imagn Images
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Making a bold trade is one of the most nerve-wracking things a Major League Baseball executive can do.

The right trade at the right time can elevate a franchise to another level, potentially leading to championship glory. But on the other hand, you risk looking like a fool in front of the global baseball audience.

Boston Red Sox first-year Chief Baseball Officer Craig Breslow made one of those trades this winter. He sent future Hall-of-Famer Chris Sale, the ace of the 2018 World Series team, to the Atlanta Braves for young infielder Vaughn Grissom.

On Sunday, Bob Nightengale of USA Today lambasted the Sale trade, calling it the worst deal the Red Sox had made in over a century.

"If the Babe Ruth trade was the worst in Boston Red Sox history, the Sale trade to Atlanta may be the second-worst," Nightengale said. "Sale will be the unanimous winner of the NL Cy Young award, leading every pitching triple crown category.  He has yielded two or fewer runs in 15 consecutive games."

Nightengale's issue with the trade wasn't just about the lopsided talent on each side. The Red Sox also came out on the wrong side of the transaction financially.

"The Red Sox not only received just infielder Vaughn Grissom in return, but they included $17 million in the deal, paying Sale’s entire 2024 salary," Nightengale said.

Judging the Sale trade in hindsight is much easier now that we know the lefty regained his ace form--and stayed healthy throughout 2024. If he makes two more starts, Sale will have played in more games in 2024 than any other season since 2017.

But trades don't happen in a vacuum, and Sale was entering what was then the final season of his contract. The Red Sox were trading for a young player who had shown flashes of real promise and came with a full six seasons of team control.

Numbers don't lie, though. Sale, with his 16-3 record, 2.46 ERA, and 206 strikeouts, has 5.5 wins above replacement in 2024. Grissom, who will turn 24 in January, has -0.6.

For Breslow and the Red Sox, it's onward and upward--there was no telling whether Sale would ever get back to this form in Boston, after all. But Sale appears poised to continue dominating in Atlanta moving forward, so the Red Sox will still be constantly reminded of the move that backfired.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org