Pirates' biggest 2026 free agency mistake should change Ben Cherington's entire offseason strategy

The Pittsburgh Pirates finally showed signs of meaningful progress in 2026, finishing with their first winning record since 2018. But one of their most expensive offseason acquisitions became a cautionary tale about the dangers of investing in reputation instead of roster fit.

Marcell Ozuna was supposed to provide the middle-of-the-order power Pittsburgh desperately needed. Instead, his one-year, $12 million contract became one of general manager Ben Cherington's most glaring mistakes.

Ozuna hit just .203/.286/.327 with eight home runs and 29 RBI in 70 games before the Pirates released him in August. Pittsburgh had invested significant resources in a designated hitter who couldn't produce enough offensively to justify occupying a roster spot, much less his salary.

Cherington acknowledged the failure when the team parted ways with Ozuna.

"We'll take responsibility for that. We just never got there," Cherington said, referring to the offensive production Pittsburgh expected from its veteran acquisition.

The admission was necessary. But with the Pirates approaching a potentially critical competitive window, acknowledging mistakes isn't nearly as important as learning how to avoid repeating them.

Pirates can't afford to make another Marcell Ozuna-sized mistake this offseason

The warning signs with Ozuna weren't particularly difficult to identify. He was entering his age-35 season after his production had already declined substantially in Atlanta. His .756 OPS in 2025 represented a significant drop from the .924 mark he posted in 2024. Pittsburgh was betting that he could reverse that trend, despite having virtually no defensive versatility to offer if his bat failed to rebound.

Signing Ozuna complicated the Pirates' defensive alignment before he played a single game. Ryan O'Hearn, originally expected to split time between first base and designated hitter, was pushed into more outfield duty. Meanwhile, Pittsburgh lost the flexibility to rotate other players through the DH spot.

When Ozuna stopped hitting, there was simply nowhere else to put him. And the Pirates, whose limited payroll already makes every significant acquisition consequential, spent $12 million learning a lesson they arguably should have understood before signing him.

Cherington acknowledged during his season-ending media availability that Pittsburgh needs to improve its run prevention, particularly defensively. That makes the Ozuna experiment especially frustrating.

The Pirates sacrificed defensive flexibility in pursuit of offensive production that never materialized. Now, with Brandon Lowe entering free agency and questions surrounding the future of third base, Pittsburgh cannot afford to approach another offseason by simply identifying recognizable veterans with impressive career statistics.

Nick Gonzales hit .303 in 2026, but his disastrous defensive metrics at third base exposed another significant roster weakness. Murf Gray's emergence in the minor leagues offers an intriguing potential solution, though counting on an unproven prospect to immediately fill a major-league need carries obvious risks.

Pittsburgh needs players who fit its actual roster, not merely players whose past accomplishments make their contracts look appealing. That means prioritizing defensive value, positional flexibility and sustainable offensive production rather than gambling on aging hitters rediscovering their former selves. It also means recognizing that taking calculated risks and repeatedly making avoidable mistakes are not the same thing.

Cherington deserves credit for eventually cutting ties with Ozuna rather than allowing a failed investment to occupy a roster spot indefinitely. But releasing an underperforming veteran doesn't erase the opportunity cost of signing him in the first place.

The Pirates have Paul Skenes, Jared Jones, Bubba Chandler and Konnor Griffin forming the foundation of what should be a competitive roster. Their window to capitalize on that talent won't remain open forever.

Pittsburgh finished 82-80 in 2026. The difference between another respectable season and a legitimate postseason run could come down to a handful of offseason decisions. The Pirates cannot keep treating expensive mistakes as acceptable growing pains.

Cherington has spent seven seasons building toward this moment. The Ozuna signing should serve as a reminder that Pittsburgh no longer has the luxury of wasting another one.

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