So maybe it isn’t Mookie Betts-level bad, but chances are that Boston Red Sox Chief Baseball Officer Craig Breslow does not look back fondly at the trade he orchestrated in late 2023.
On Dec. 30 of that year, Boston sent veteran left-hander Chris Sale and $17 million to the Atlanta Braves for infield prospect Vaughn Grissom. And at the time, it made sense.
Sale, who had a year left on his contract at $27.5 million with a $20 million club option for 2025, had missed a significant amount of time over the previous four seasons. Sale sat for all of 2020 and most of 2021 after Tommy John surgery; pitched just 5.2 innings over two starts in 2022 due to a right rib stress fracture, then a broken finger suffered during his comeback attempt; and dealt with a shoulder problem that put him on the injured list for over two months in 2023.
As for Grissom, he was a well-regarded prospect for the Braves who had posted a .330/.419/.501 slash line that summer for the Triple-A Gwinnett Stripers. There were some in the Red Sox organization who felt that Grissom would fit nicely into the team’s open spot at second base.
But that didn’t happen. Grissom hit .190 in 31 games for the Braves in 2024, 30 of them at second base, instead spending most of his time either on the injured list or struggling to a .259 average with Triple-A Worcester. And all Sale did that season was go 18-3 with a 2.38 ERA, winning the NL Cy Young Award.
Insider Suggests Boston is Ready to Move on From Infielder Vaughn Grissom
In hindsight, it was not Breslow’s finest transaction. And according to a recent report, the Red Sox may be prepared to close the door entirely on the whole thing.
In an article last Thursday for MassLive, Red Sox analyst Chris Cotillo examined various scenarios for the team should Alex Bregman and Trevor Story both end up signing with different teams this offseason. While that would theoretically open an opportunity at the big league level for Grissom, who remained at Worcester throughout all of 2025, Cotillo didn’t seem to think the now 24-year-old would be in Boston’s plans.
“Vaughn Grissom remains on the 40-man roster but is one of the more clear change-of-scenery candidates in baseball after not cracking the big league roster once in 2025,” he opined.
By the middle of 2025, it had become clear that whatever upside Boston hoped to find in Grissom wasn’t materializing. The once-hyped infielder looked more like a stalled project than a player on the cusp. His contact skills, once praised as elite, had flattened out in Worcester, where he hit just .270 with sporadic power and inconsistent defense.
Even when healthy, Grissom rarely showed the spark that had made him such an appealing piece to the Braves a few years earlier. The Red Sox showed their hand with various in-season call-ups that did not include Grissom, and in a July interview with MassLive, Grissom indicated that the writing seemed to be on the wall as far as his future with the Red Sox was concerned.
“I don’t really expect much more opportunity here just because decisions that were made were made, and it kind of didn’t involve me,” he said. “I mean, all those decisions, they make sense in a way, but I guess it sucks a little bit.”
Team sources and minor league staff haven’t exactly gone out of their way to dispute it either. When Grissom’s season ended in early September due to plantar fasciitis, WooSox manager Chad Tracy made a rather telling comment.
“Despite the amount of times that other guys were called and his name wasn’t,” Chad Tracy said. “… It was nice to work with him.”
Vaughn Grissom Struggled With Boston, While Chris Sale Dominated in Atlanta
Meanwhile, the 36-year-old Sale followed his 2024 Cy Young campaign with another All-Star season in 2025, posting a 2.58 ERA in 21 appearances, 21 of them starts, and he struck out 165 batters in 125.2 innings. Despite missing time with a fractured rib, Sale – whose contract had been extended following the trade to Atlanta, with an $18 million club option for 2026 – will again be counted on to be a leader of the Braves staff.
It’s hard to imagine a starker contrast. Sale, continuing to dominate, while Grissom is still trying to prove he belongs in the majors at all.
Boston’s gamble — moving on from an expensive, aging pitcher in exchange for a promising infielder — was defensible at the time. But two years later, it looks like one of the more regrettable deals in recent Red Sox memory, a decision driven by caution and accounting that cost them a Cy Young winner in exchange for a depth piece they may soon cut loose.
No one’s saying it’s the second coming of the Betts fiasco, but it is certainly one that Craig Breslow would rather forget.
Like Heavy Sports’s content? Be sure to follow us.
This article was originally published on Heavy Sports
The post Red Sox Ready to Close the Book on a Regrettable Decision appeared first on Heavy Sports.