Ranking Pirates’ most realistic free-agent targets based on Ben Cherington’s recent offseason history

The Pittsburgh Pirates have plenty of options in free agency this winter. But if fans want to predict which players general manager Ben Cherington might actually sign, his recent offseason history is probably a better starting point than any list of the market's biggest names.

Cherington has developed a fairly recognizable approach to free agency during his tenure in Pittsburgh: prioritize short-term commitments, target veterans with something to prove, find value in overlooked players and avoid getting locked into expensive long-term contracts.

Consider the Pirates' recent acquisitions. In 2024, Pittsburgh signed Aroldis Chapman, Martín Pérez and Michael A. Taylor to one-year contracts. The following offseason brought Andrew Heaney, Tommy Pham, Adam Frazier and Caleb Ferguson, again on one-year deals.

Last winter represented something of a departure from that strategy. Ryan O'Hearn received a two-year, $29 million contract, while Marcell Ozuna signed for one year and $12 million. Gregory Soto joined on a one-year, $7.75 million deal.

Those signings suggested Cherington was becoming more willing to spend, but they didn't completely abandon his preference for manageable commitments. Even O'Hearn's deal was only for two seasons.

Now, with Cherington insisting at the GM Meetings that he doesn't feel financially "hamstrung or constrained," Pittsburgh's options appear relatively open. Still, its expanding arbitration class, existing contracts and uncertainty surrounding Brandon Lowe's free agency could influence how aggressively the front office pursues outside additions.

Based on the types of players Cherington has targeted over the past several winters, these six free agents stand out as particularly realistic possibilities, ranked from least to most likely.

Ranking Pirates’ most likely free-agent signings based on Ben Cherington’s past moves

6. Daulton Varsho, OF

Varsho represents a familiar Cherington archetype: a talented veteran whose declining production and injury concerns could create an opportunity to buy low.

The 30-year-old outfielder struggled offensively in 2026, producing a .637 OPS between Toronto and Houston before undergoing wrist surgery in September. His disappointing season could limit his earning potential, potentially making a short-term, prove-it contract attractive.

Varsho brings considerable defensive value, having previously won a Gold Glove, and he could give the Pirates another option in the outfield. Unfortunately for Pittsburgh, he's another left-handed hitter joining a lineup that already struggled mightily against left-handed pitching.

Pittsburgh went 18-33 against left-handed starters in 2026, and adding Varsho wouldn't necessarily address that weakness. His health also creates uncertainty. Cherington has demonstrated a willingness to take chances on veterans looking to rebuild their value. Whether Varsho is the right gamble is another question.

5. Robbie Ray, LHP

If Cherington decides the rotation needs another experienced arm, Ray fits his historical approach surprisingly well.

Remember Pittsburgh's signings of Pérez in 2024 and Heaney in 2025? Both were veteran left-handers added on relatively inexpensive one-year contracts to provide stability without requiring long-term commitments. Ray could theoretically fill a similar role, particularly if the Pirates decide to move Mitch Keller or want additional insurance behind their young rotation.

MLB Trade Rumors projected Ray for a one-year, $12 million contract, a figure that wouldn't represent an unprecedented investment for Pittsburgh. However, other projections have suggested Ray could command a significantly larger deal, which would make him a less natural fit for Cherington's usual strategy.

Unlike previous offseasons, the Pirates aren't necessarily desperate for another established starter. Ray makes sense if the price and circumstances align. He becomes substantially less realistic if Pittsburgh has to win a bidding war.

4. J.P. Crawford, INF

Few free agents check as many traditional Cherington boxes as Crawford. He's an established veteran, offers positional flexibility, possesses a strong understanding of the strike zone and could be available on a relatively affordable contract.

Two MLB Trade Rumors writers have already predicted that Crawford will sign with Pittsburgh, with the publication projecting a two-year, $16 million deal. That kind of commitment would fall comfortably within the range Cherington demonstrated with O'Hearn last offseason.

Crawford also offers the kind of patience at the plate that Pittsburgh desperately needs. His 13.1% walk rate in 2026 would be a welcome addition to a lineup that frequently struggled with strikeouts and inconsistent offensive approaches.

But there are obvious limitations. Crawford hit just .221/.335/.352 with 14 home runs last season. His defense at shortstop has declined, potentially requiring a move to second or third base. And, once again, he's a left-handed hitter.

Crawford is precisely the kind of affordable, experienced player Cherington has traditionally favored. He just isn't the kind of offensive difference-maker Pittsburgh needs if Lowe departs.

3. Alec Bohm, 3B

Bohm might be one of the more intriguing combinations of immediate roster fit and historical precedent.

Pittsburgh needs to improve defensively at third base, but it also needs another reliable right-handed bat. Bohm addresses the latter concern while offering a potential short-term bridge until top prospect Murf Gray is ready.

The former Philadelphia Phillies infielder endured an uneven 2026 season, finishing with a .249/.315/.383 slash line and 15 home runs. However, he still drove in 88 runs and performed considerably better after a dreadful start. His offensive inconsistency could make him a candidate for the kind of shorter-term contract Cherington has pursued with other veterans.

Bohm also produced an .816 OPS against left-handed pitching last season, giving Pittsburgh a legitimate reason to pursue him beyond simply filling an opening on the infield.

He isn't an ideal defensive solution at third base, and the Pirates would need to weigh that weakness carefully after their defensive struggles in 2026. Still, Bohm offers more obvious offensive upside than some of the inexpensive alternatives available.

2. Tyrone Taylor, OF

If there's a free agent who looks like he belongs in a classic Ben Cherington offseason, it's Taylor.

The veteran outfielder isn't a headline-grabbing name, but his combination of defensive versatility, experience and potentially modest contract demands makes him a remarkably logical target.

Pittsburgh has previously made similar investments in Michael A. Taylor and Tommy Pham, both veterans signed to short-term deals to address immediate outfield needs.

More importantly, Taylor would address an actual weakness in the Pirates' lineup. He posted a .921 OPS against left-handed pitching in 2026, making him an attractive option for a team that finished last in baseball in batting average, on-base percentage and slugging percentage against southpaws.

Taylor also provides defensive flexibility across the outfield, allowing the Pirates to rotate players through the designated hitter spot without sacrificing as much defensively.

Would Taylor transform Pittsburgh's lineup? Absolutely not. But as an affordable complementary addition, he checks almost every box Cherington has traditionally prioritized. Given that Pittsburgh already has Bryan Reynolds, Oneil Cruz, Esmerlyn Valdez and Jake Mangum in its outfield picture, a reasonably priced veteran role player makes more sense than committing significant money to another everyday outfielder.

1. JoJo Romero, LHP

If we're ranking these players strictly according to Cherington's previous offseason behavior, Romero deserves the top spot.

Few positions have received as much consistent attention from Pittsburgh's front office as the bullpen, particularly when experienced left-handed relievers are available.

Chapman signed for $10.5 million in 2024. Ferguson joined on a $3 million deal ahead of 2025. Soto received $7.75 million last winter. And with Soto back on the open market, Pittsburgh once again has an obvious need for another dependable left-handed reliever.

Romero posted a 3.36 ERA across 55 appearances in 2026, splitting the season between St. Louis and Milwaukee. He also contributed to the Brewers' World Series championship run, providing valuable late-inning experience.

MLB Trade Rumors projected the 30-year-old for a two-year, $13 million contract, which would be a relatively manageable commitment for an experienced leverage reliever. Pairing Romero with Mason Montgomery would give the Pirates another dependable left-handed option while preserving flexibility in the later innings.

There would be some risk in extending a multiyear contract to a reliever, particularly given Cherington's preference for one-year bullpen investments. But the projected annual salary is reasonable, and Romero would fill a clear need.

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