Suffice to say that 51-year-old Ben Cherington is not the most popular general manager the Pittsburgh Pirates have ever had. According to writer John Perotto of Pittsburgh Baseball Now, “the general feeling is that Cherington is in his final months as the Pittsburgh Piratesâ general manager.”
The feeing is perhaps understandable. Since taking over Pittsburgh’s baseball operations in November, 2019, Cherington’s Pirates teams have finished in last place in the National League Central three times, and in fourth place twice. After 100 games in 2025, the Pirates are in the basement again.
Before the Pirates, Cherington was GM of the Boston Red Sox, holding that position from 2012 through 2015. In his second season, the Red Sox won a surprise World Series championship and Cherington was named executive of the year. But in his other three seasons, the Red Sox occupied the cellar in the American League East.
Anxiety Among Pirates Fans Over Trade Deadline
With the 2025 trade deadline fast approaching, the anxiety among Pirates fans and media about moves Cherington may make is growing.
“Cherington has made plenty of blunders as the Pirates’ general manager,” wrote FanSided Pirates correspondent Noah Wright. “But this one would be his biggest.”
What is Wright talking about? The answer is, a much-rumored trade of Pirates veteran starting pitcher Mitch Keller.
“The team is bad, and Keller holds a lot of value,” Wright wrote on Saturday. “The way he’s pitching at the moment also gives (Pirates owner) Bob Nutting a chance to get out of the remaining $60 million on his contract. It all makes sense.”
According to one report out of Pittsburgh, the chance that Cherington will ship out Keller by the deadline could be be as high as 70 percent, with the Chicago Cubs, New York Mets and New York Yankees reportedly among the teams ready to make a bid for the 29-year-old 2014 Pirates second-round draft pick.
But according to MLB analyst Ryan Garcia of Empire Sports Media, the Yankees “should be all over this reliable veteran starter.”
Keller before last season signed a five-year, $77 million contract extension with Pittsburgh.
Keller Can be Counted on to Make His Starts
“When you re-calculate the Luxury Tax hit (the AAV is determined by the remaining money and years left after a trade), Mitch Keller should be owed a bit under $18 million a year,” Garcia wrote on Monday. “Frankie Montas ($17 million), Marcus Stroman ($18.5 million), and Alex Cobb ($15 million) were all much greater health risks who signed in their 30s with worse production and intelligent organizations handed out those deals.”
Montas went to the Mets, Stroman to the Yankees and Cobb to the Tigers.
What does Keller offer the Yankees for his price tag?
“At the age of 29, youâd have Keller through his age-32 season, which is an absolute steal since you would only get his peak years and none of the late-stage ugliness you see with a starter whose stuff completely diminishes.” Garcia wrote.
Keller was an All-Star in 2023, and has posted a career-low 3.86 ERA through 20 starts so far this year. He has delivered at least 2.0 wins above replacement (WAR) in each of the last three seasons. But perhaps his most important quality for the Yankees’ injury-riddled pitching staff was identified by the Pirates writer, Wright.
Reliability.
“Reliability is a hard thing to find in baseball today. With constant arm injuries and Tommy John surgeries, finding a pitcher who you can count on for at least five innings every outing (and for 30 starts a season) is hard to find,” he wrote. “There is no replacement for what Keller brings to the Pirates.”
That is exactly why the Yankees would be interested in acquiring Keller.
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