Red Sox 'Disastrous Deal' Predicted To Negatively Affect Boston's 2025 Season

Some trades barely get remembered, while others live in infamy for decades to come. The trade the Boston Red Sox made last winter will go down in the latter category.

Aug 28, 2024; Minneapolis, Minnesota, USA; Atlanta Braves starting pitcher Chris Sale (51) delivers a pitch against the Minnesota Twins during the second inning at Target Field. Mandatory Credit: Matt Krohn-Imagn Images Matt Krohn-Imagn Images

In December of 2023, the Red Sox traded now-eight-time All-Star starting pitcher Chris Sale to the Atlanta Braves for second baseman Vaughn Grissom. Because Sale had been injured for most of the previous five seasons, they also kicked in $17 million in cash to ship the lefty to Atlanta.

Unfortunately, things unfolded about as poorly as they could have from the Red Sox's perspective.

While Grissom never earned the full-time starting job and spent more than half of his season in Triple-A, Sale found his form like never before. He won the National League's pitching Triple Crown and took home his first Cy Young Award at age 35.

As if that wasn't bad enough, Bleacher Report's Kerry Miller predicted on Wednesday that Boston's pain would continue, naming the Sale trade as one of the Top 10 recent "trade fails" that would haunt teams in 2025 and beyond.

"Knowing now how the 2024 season played out—Sale winning the NL Cy Young for Atlanta; Grissom doing absolutely nothing for the Red Sox while an underachieving starting rotation 'led' them to a third consecutive year of mediocrity—this looks, in retrospect, like an all-timer of a disastrous deal for Boston," Miller wrote.

"It's plausible Grissom never plays again for the Red Sox, which would cement this swap as one of the most lopsided deals in decades."

Fortunately, the Red Sox's rotation is in a better place now than it was a year ago, so watching Sale dominate shouldn't be quite as painful as it was to begin with. Plus, the contract Sale had with Boston would have expired after the 2024 season; the Braves were wise to extend him for two more years before he ever threw a pitch for them.

But there's no denying it: the Red Sox needed Grissom to pan out as a big-leaguer for the trade to give them any sort of return value. And because it was the first big move of Craig Breslow's tenure as Chief Baseball Officer, the stink of this deal has the potential to follow the front office for years to come.