The Pittsburgh Pirates’ offseason was always going to be judged through a pretty simple lens: Did they do enough to support a young, electric pitching staff and a lineup that badly needed competent Major League offense?
Less than two months in, the answer is complicated. Some of Ben Cherington’s moves look genuinely sharp — the kind of targeted, cost-conscious additions that make a front office look like it knew exactly where the market inefficiencies were. Others look like the same old Pirates trap: hoping rebound candidates, aging bats and cheap pitching depth can solve problems they were never equipped to solve.
So, with the benefit of early-season results, here are three Pirates offseason decisions that look genius — and two that look awful.
3 Pirates offseason decisions that look genius
Signing Ryan O'Hearn (2 years, $29 million)
Ryan O’Hearn was never going to be the flashiest addition on the market, but he gave Pittsburgh exactly what it lacked: a professional left-handed bat with real power, a track record of producing against right-handed pitching and enough defensive flexibility to make the roster fit work.
For a team that spent too much of last season cycling through inconsistent offensive pieces, O’Hearn brought stability. He lengthened the lineup. He gave Don Kelly a dependable middle-order option. And in a Pirates offense that still has plenty of swing-and-miss, his ability to put together competitive at-bats has mattered.
The Pirates didn’t need every offseason move to be a superstar swing. They needed more credible major-league hitters. O’Hearn has been exactly that.
Ryan O’Hearn has homered in back-to-back games and has produced multi-hit performances in three of his last five. Here’s O’Hearn on how an adjustment to his setup has helped him turn the tides offensively. — From José Negron in Pittsburgh pic.twitter.com/qcEfg7wPbo
— DK Pittsburgh Sports (@DKPghSports) May 14, 2026
Three-way trade that landed Brandon Lowe, Jake Mangum and Mason Montgomery
This one has aged beautifully.
The Pirates’ three-team deal with the Tampa Bay Rays and Houston Astros could have been viewed as a little risky at the time. Brandon Lowe came with injury history. Jake Mangum was not exactly a household name. Mason Montgomery was more of a pitching-depth upside play than a guaranteed rotation answer. But the early returns have made the trade look like one of Pittsburgh’s smartest offseason gambles.
Lowe has given the Pirates legitimate impact from the left side, including the kind of power production this lineup desperately needed. Mangum, meanwhile, has become more than just a depth outfielder. He has fit the identity of this team almost perfectly — energetic, useful, versatile and somehow central to the “Hoist the cone” weirdness that has become part of the club’s personality.
Montgomery has also given the Pirates another arm to work with as Kelly continues experimenting with openers, bulk innings and nontraditional pitching roles. That’s a whole lot of value from one trade — especially when you consider that Pittsburgh only gave up one woefully underperforming pitcher in Mike Burrows.
Signing Gregory Soto (1 year, $7.75 million)
For all the understandable attention on Pittsburgh’s rotation, the bullpen was always going to determine how far this team could actually go. The Pirates had too many question marks in relief to simply hope everything would sort itself out internally.
Gregory Soto was not a perfect reliever when they signed him. He has always had some volatility. But the appeal was obvious: premium velocity, a swing-and-miss slider and experience pitching in leverage.
So far, Soto has looked like the kind of aggressive move the Pirates are often criticized for not making. They identified a need and addressed it with actual upside.
Gregory Soto, Wicked 83mph Sweeper. 🤢 pic.twitter.com/9nkDLFqlsk
— Rob Friedman (@PitchingNinja) April 16, 2026
3 Pirates offseason decisions that look awful
Signing Marcell Ozuna (1 year, $12 million)
The Pirates needed offense, yes. But they also needed athleticism, defensive flexibility and a roster that did not box them into awkward alignments. Marcell Ozuna gave them a bat-only player at a point when the roster was already trying to figure out where Oneil Cruz fit best, how to balance young hitters and how to keep enough flexibility for in-game maneuvering.
Instead, Ozuna’s presence clogged the DH spot and made the outfield feel even more rigid. Both Cruz and Bryan Reynolds have struggled defensively, but there's no easy pivot to remove them from the field while keeping their bats in the lineup. Now that Ozuna isn't producing enough to justify being a full-time DH, the roster construction looks even worse.
The Pirates were right to chase offense. They were wrong to chase this version of it.
Signing José Urquidy (1 year, $1.5 million)
The idea was understandable. The execution has been rough.
José Urquidy was brought in as a veteran arm who could provide length, stabilize games and give the Pirates another option as they managed workloads across a young pitching staff. In theory, that made sense. In practice, it fell apart quickly.
Urquidy’s struggles were hard to ignore. He was hit around, failed to give the bullpen the kind of dependable innings the Pirates needed and was ultimately optioned after posting ugly early numbers. For a team already trying to be careful with its starters and creative with its pitching usage, an ineffective long man creates a ripple effect.
This offseason proved the Pirates were capable of making smart, creative moves. O’Hearn, Soto and the Lowe-Mangum-Montgomery trade all addressed real needs. They made the roster better.
But Ozuna and Urquidy are reminders of the other side of this front office’s approach: too much faith in flawed fits, fading veterans and low-cost upside plays.
The Pirates didn’t have a bad offseason; they had an uneven one. And in a division where the margin is still thin, the difference between genius and awful might end up mattering more than they expected.
