Pirates GM in Tough Spot Ahead of Trade Deadline

PITTSBURGH — The Pittsburgh Pirates front office has a busy next two days before the end of the MLB trade deadline on July 31, including the general manager.

Pirates general manager Ben Cherington is in his sixth season with the Pirates and they're in the midst of another lost season.

The Pirates sit 46-62 overall, 18.5 games back of the Milwaukee Brewers in first place of the National League Central Division, 13.0 games back from a Wild Card spot and the fifth worst record in all of baseball.

This season looked like one that Cherington would finally have some success, at least in planning years before, but a lack of development from hitters has the Pirates near or at the bottom of most hitting metrics.

Cherington already dealt Adam Frazier to the Kansas City Royals on July 16 and will almost certainly move players they signed for one-year deals in outfielder Tommy Pham and left-handed pitchers in starter Andrew Heaney and Caleb Ferguson, plus shortstop Isiah Kiner-Falefa, who is in the last year of his two-year, $15 million contract.

He also has a conundrum will selling players with longer team control, such as bullpen duo in right-handers David Bednar and Dennis Santana, who both will command great returns, as they have a year of club control and have had excellent 2025 campaigns.

Cherington may also move players they signed on long-term contracts, like right-handed starting pitcher Mitch Keller, third baseman Ke'Bryan Hayes and outfielder Bryan Reynolds, but recent reports indicate they haven't made a decision on moving their long-term players, particularly Keller, who is in the second of a five-year deal he signed in Feb. 2024.

Ken Rosenthal of the The Athletic reports that Cherington is in a tough spot heading into the trade deadline, as if he plays it too safe and the Pirates continue going downward, he'll get fired, and if he trades great pieces away and then the Pirates don't have early success, he'll also lose his job.

"By awarding president of baseball operations Jed Hoyer a contract extension, the Chicago Cubs effectively reduced the pressure on him at the deadline, at least as far as his job security was concerned," Rosenthal wrote.

"Pittsburgh Pirates GM Ben Cherington, on the other hand, remains in limbo, and not without reason. Hoyer’s team is well-positioned for a playoff berth. Cherington’s is headed for a sixth straight losing season.

"The question is how owner Bob Nutting will evaluate Cherington’s performance at the deadline and beyond.

"If Nutting judges Cherington partly on how the Pirates finish, a sell-off involving Bednar, Mitch Keller and others likely would make the team even less competitive, damaging the GM’s standing.

"But if Cherington takes a passive approach, declining to leverage his ample supply of pitchers to acquire impact hitters, Nutting could fire him for a different reason — failing to put the team in better position for 2026.

"History suggests that treading lightly could be the wrong play. In 2019, then Pirates-GM Neal Huntington moved rentals Corey Dickerson and Jordan Lyles at the deadline but held on to several rentals and valuable veterans. The Pirates were 47-61, compared to 44-62 now. Nutting fired Huntington after that season.

"The situation is awkward, to say the least. Whatever path Cherington chooses, he might be doomed."