For years, Ben Cherington has walked the wary path. Known around the league as a meticulous, often overly conservative decision-maker, the Pirates’ GM has built a reputation for overanalyzing trades and overvaluing his own assets. But 2025 might just be the year he breaks that mold. “I could see this being a year where he steps out of his comfort zone,” a source told the Post-Gazette. Another insider echoed the shift, adding Cherington “seems more open to making a bigger move than usual.” The safe GM could now be on the edge of a bold new chapter.

That change in mindset has become increasingly apparent as the trade deadline nears, and rival clubs are taking notice. The Phillies, for one, are showing strong interest in a $7.3 million (in combined salaries) bullpen duo that has caught fire lately. Right-handers Dennis Santana and David Bednar have emerged as two of the most dominant relief alternatives on the market, and the Phillies have inquired about both. Per reports, Philadelphia has “thought highly of Santana for quite some time,” making him their primary target, but Bednar’s recent surge has also caught their attention.

What makes the scenario more intriguing is how the Pirates are handling the action. Sources believe the organization has been deliberately “leaking” player names to stir interest and drive up offers, an uncharacteristically assertive move under Cherington’s tenure. For a GM who is often viewed as hard to negotiate with, letting teams come to him first and floating assets proactively signals a notable shift. After five years of conservative maneuvering, he is now playing the market, not guarding it.

And with Santana and Bednar still under team control through 2026, the GM of the Phillies has the leverage he rarely pushes this hard. If Cherington truly steps outside his usual comfort zone, this could be the deadline that defines his managerial era in the Pirates. Whether it is job security, roster urgency, or a bit of both pushing the pivot, one thing is clear—Ben Cherington is ready to deal distinctively, and the Phillies could be the first team to cash in.

While Cherington is making headlines for considering vital bullpen deals, the Phillies are quietly preparing for a roster shakeup of their own. And one star sitting on the hot seat?

All eyes are on the bullpen, but the outfield could face a shakeup, too

Outfielder Max Kepler is on the hot seat. Once identified as a shrewd $10 million signing, Kepler’s 2025 campaign has not panned out. Through 78 games, the star is slashing just .210/.685 with 10 homers and 30 RBIs—well off Kepler’s career pace. The star’s underwhelming performance comes despite being thought to play an everyday role; however, Max Kepler has now slipped into an awkward platoon with just three starts all against left-handers.

The squad has not exactly helped either. Kepler has been just as unproductive versus righties (.210 average) as he is against southpaws (.213). The initial gamble now looks more like a misfire, and with the trade deadline looming, his roster spot could be collateral damage if Philadelphia lands an impact outfielder. According to Fansided’s Edward Eng, “the experiment is starting to feel like it isn’t working,” which only adds to the urgency. His $10 million one-year deal makes him an easy contract to move, particularly for a contender looking to reset and reestablish in key areas.

All signs point to the Phillies going all-in, both to patch their team and possibly refresh their outfield. With limited time left to capitalize on their current championship window, roster flexibility is vital. And if a bold bullpen deal goes through, do not be surprised if a big-name hitter like Kepler is the next domino to fall.

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