3 Pirates making Ben Cherington's 2026 trade deadline decisions more difficult by the day

Ben Cherington’s trade deadline calculus should be simple. The Pittsburgh Pirates need bullpen help, they need more lineup stability, and they need to stop pretending that internal improvement alone can solve problems that have been obvious for months.

But as the Aug. 3 deadline approaches, the Pirates have a few players making those decisions more complicated by the day — not necessarily because they're all helping, but because their situations force the front office to answer uncomfortable questions about roster construction, role security and how much patience a contending team can afford.

Three players in particular are creating different kinds of headaches for Cherington. One is barely producing but apparently not going anywhere. One is supposed to be the closer but is trending in the wrong direction. One looked like a lost cause a month ago but is suddenly making a case to matter again. Together, they represent the gray area that makes this deadline so important.

3 Pirates players complicating Ben Cherington's 2026 trade deadline decisions

Marcell Ozuna

Let's start with the obvious one. Marcell Ozuna’s numbers through June are impossible to dress up: .200/.279/.324 with a 67 wRC+. That's dead-weight production for a player whose entire value is supposed to come from offense.

And yet, the Pirates don't appear eager to move on. Cherington has made it clear that Pittsburgh values Ozuna’s presence in the dugout, even though his playing time has dried up (for obvious reasons). But at some point, that argument runs into reality. The Pirates aren't paying Ozuna $12 million to be a bench coach, even if that's effectively what his role has started to resemble.

If the Pirates are truly trying to upgrade their roster at the deadline, then every spot matters. Carrying a bat-first veteran who's not hitting or even playing regularly limits flexibility. It makes it harder to add another bench bat. It makes it harder to keep a younger player who might offer more athleticism, defensive value or upside. It also makes it harder to justify acquiring offensive help if the organization is unwilling to admit that one of its internal roster spots has already become a problem.

Ozuna’s presence doesn't necessarily stop the Pirates from making a move. But it forces Cherington to decide whether reputation and clubhouse value are enough to keep protecting a roster spot that could become increasingly important in August and September.

Gregory Soto

Gregory Soto has now allowed at least one earned run in five of his last eight appearances, which is the kind of stretch that would usually put a closer’s role in danger. The problem, though, is that Pittsburgh doesn't have a clearly superior alternative waiting behind him.

The entire bullpen has been unstable. Roles are undefined. Trust has been hard to build and even harder to maintain. Soto is still the closer largely because the Pirates don't have anyone else who has definitively taken it from him. But that doesn't mean his grip on the job should be unquestioned.

If the Pirates had a dominant right-handed reliever, Soto’s recent struggles would be a much bigger story. If they had a reliable internal setup option, they could at least consider easing him out of the highest-leverage spots for a week. Instead, they may have no choice but to let Soto work through it while still receiving the majority of save chances. That's a dangerous place for a team with postseason aspirations.

Soto’s slump makes Cherington’s deadline harder because it sharpens the bullpen need without offering an obvious internal solution. The Pirates already needed relief help. Now they may need someone capable of pushing their closer, not just supporting him.

That's a much different ask. Middle relief depth is one thing. A late-inning arm who can handle the eighth or ninth is more expensive. If Soto steadies himself, Pittsburgh can target one strong setup option and feel better about the overall structure. If he keeps leaking runs, Cherington will have to shop like a team without a true closer.

Dennis Santana

Dennis Santana may be the most interesting name in this group because he's making Cherington’s job harder by pitching better.

A little more than a month ago, Santana looked nearly unplayable. He wasn't locating well enough, and he couldn't be trusted in leverage. But since then, he has quietly posted a zero in eight of his last nine outings.

That is not a small development. The Pirates desperately need a right-handed reliever to stabilize the bridge to Soto, and Santana has done that job before. The question is whether Cherington can afford to believe this version is here to stay.

If Santana continues pitching well, the Pirates might be tempted to view him as one of their internal bullpen fixes. Pair him with Isaac Mattson, who has allowed just one run over six innings since being recalled from Triple-A Indianapolis on June 13, and the right-handed relief picture suddenly looks a little less bleak.

Santana’s rebound should help the Pirates, but it shouldn't convince them they are done. A good nine-outing stretch is encouraging, but it does not erase the volatility that came before it. The same applies to Mattson’s smaller sample. These are positive signs, not deadline solutions by themselves.

Santana is making Cherington’s decision harder because he gives the front office something to believe in. But belief isn't a bullpen plan. If anything, Santana’s resurgence should give the Pirates more reason to add, not less. A bullpen with Santana as one of multiple reliable right-handed options is much stronger than a bullpen depending on Santana to be the answer.

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