4 nightmare scenarios for the Pittsburgh Pirates at 2025 trade deadline

The Pittsburgh Pirates are firmly in the driver's seat as one of baseball's biggest sellers, fielding inquiries from teams all over the league this week ahead of the July 31 MLB trade deadline. But with great power comes great responsibility.

The Pirates have leverage at this year's trade deadline, and it's up to general manager Ben Cherington to use it wisely. If he doesn't, the Pirates could find themselves in one of the following nightmare scenarios.

4 nightmare scenarios for the Pittsburgh Pirates at 2025 trade deadline

Pirates trade Mitch Keller, only to find out Bubba Chandler isn't ready for the big leagues

One of the most reliable members of the Pirates' starting rotation, Mitch Keller has generated quite a bit of buzz leading into this week. He's expendable, some would argue, because the Pirates have an elite starting pitching prospect in Bubba Chandler coming right behind him. But what if the Pirates trade Keller and call up Chandler, only for Chandler to flop? While not likely to happen, it would majorly impact the Pirates' plans both now and in the future.

Now, replace Keller's name with Andrew Heaney's, and it's an entirely different story. The Pirates trade Heaney for whatever he's worth as a back-end starter on an expiring contract and bring up Chandler to give him a shot. Even if it goes horribly, the Pirates aren't any worse off heading into 2026 than they otherwise would have been.

Pirates get fleeced in a David Bednar trade

At this stage, David Bednar is the most valuable reliever available on the trade market – and it's not even close. Contenders are always looking for bullpen help, and pitchers with his ability to thrive in leverage situations – and with years of team control remaining – don't come available every day.

If the Pirates are going to trade their two-time All-Star closer, they have to get this one right. This is a legitimate opportunity to turn their wealth of high-quality pitching into some high-quality bats to provide run support for the pitchers they end up keeping.

Pirates trade Ke'Bryan Hayes and get nothing impactful in return

The Pirates finally deal their Gold Glove third baseman, but the return is underwhelming: a low-ceiling Double-A pitcher and a fringe outfielder. Maybe throw in a low-level teenaged international prospect who will never even sniff the Majors. Hayes thrives with his new team, and Pittsburgh’s lack of patience becomes the latest chapter in a familiar story.

It's almost too easy to picture it because it would be so, painfully on-brand.

Pirates do nothing at the trade deadline

No one is calling this a likely scenario, but it could happen – and it would, in fact, be a nightmare. And if it does happen, Cherington's bags may as well be packed already.

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