Dennis Santana is twisting the knife in Pirates’ desperate playoff chase

There might not be a more maddening subplot to the Pittsburgh Pirates’ 2026 season than Dennis Santana suddenly becoming unhittable for the team they are desperately trying to catch in the Wild Card standings.

With Pittsburgh, Santana posted a 6.05 ERA and played a direct role in multiple crushing losses. He entered the season expected to handle high-leverage innings and potentially establish himself as the Pirates’ closer. Instead, he became one of their biggest liabilities and was booted off the 40-man roster in July.

Now? Santana owns a 1.29 ERA with the Arizona Diamondbacks. Because of course he does.

The timing has made it even worse. On Monday against the Kansas City Royals, Santana protected a 5-4 lead in the 10th inning to earn his third save of the season. The next night, he struck out three while allowing one hit in another scoreless inning. Those are games Arizona needs badly — and they're also games Pittsburgh desperately needs Arizona to lose.

That makes watching Santana thrive particularly painful for Pirates fans, because this isn't some random former middle reliever having a nice month somewhere else. Santana was supposed to be an important part of Pittsburgh's bullpen. His inability to hold leads contributed to several losses during a season in which the Pirates are now agonizing over every game separating them from a Wild Card spot.

It's impossible not to wonder how different the standings might look if Pittsburgh had received anything close to this version of Santana this year. But there also needs to be some restraint before turning Santana's success into another indictment of the Pirates' coaching staff or front office.

Relievers are weird. And Santana might be the perfect example.

The Pirates themselves benefited from exactly this phenomenon when they claimed him off waivers from the New York Yankees. Sometimes a pitcher changes organizations, makes a minor adjustment, finds a role he likes or simply catches fire for a few months. Then it disappears just as quickly.

Pirates former bullpen problem Dennis Santana is now helping bury their playoff hopes with Diamondbacks

That's the uncomfortable reality with pitchers like Santana. The talent is clearly there, but consistency rarely follows it for very long. If Santana were permanently the pitcher currently dominating for Arizona, he probably wouldn't have bounced around enough for Pittsburgh to acquire him off waivers in the first place.

The Pirates were justified in moving on when they did. A team trying to stay in contention couldn't indefinitely keep running a struggling reliever into high-leverage situations hoping that the good version would eventually return. Arizona simply happened to get that version next.

Santana can now be added to an increasingly long list of “what ifs” surrounding this Pirates season. What if the bullpen had stabilized earlier? What if Santana had converted even a few more of those late leads? What if Pittsburgh hadn't spent so much of the summer giving away games that suddenly look enormous in September?

There is no guarantee keeping Santana changes anything. But watching the pitcher who helped bury the Pirates in several games now help Arizona win the very games Pittsburgh needs the Diamondbacks to lose? That's irony in its cruelest form.

And in a season that could ultimately be decided by only a handful of games, Dennis Santana's bizarre journey from Pirates problem to Diamondbacks weapon might end up being one of the strangest and most painful storylines of them all.

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