4 Pirates targets who could come off the board quickly at the Winter Meetings

As the 2026 Winter Meetings approach, the Pittsburgh Pirates have reportedly been linked to not just one, but multiple names that actually make sense for this roster.

We're talking real bats. Real fits. Real answers to real problems. And that's exactly why Pirates fans are bracing for disappointment –– because some of the names they're being linked to are guys who aren't waiting around for Ben Cherington to finish "checking in."

The Pirates will have to get uncomfortably aggressive if they want to land one of these players at the Winter Meetings because these guys are going to move –– fast.

3 Pirates targets who could come off the board quickly at the Winter Meetings

Jeff McNeil (IF/OF, New York Mets)

Jeff McNeil is the type of player the Pirates always talk themselves into –– left-handed, multi-position, high contact history, with a "bounce-back" argument ready-made. Which is exactly why half the league sees him that way, even at a steep price of $15.75 million with an option for 2027.

McNeil isn’t just a Pirate target. He’s a plug-and-play contender bat. Someone who shortens a lineup instantly for a team that’s already good — and those teams don’t negotiate slowly. If McNeil is available –– and it appears that he is –– some playoff team is going to treat him like duct tape for October: not glamorous, but essential.

The Pirates don’t live in that marketplace. They live in the one where “we tried” gets printed instead.

Jarren Duran (OF, Boston Red Sox)

Jarren Duran is a spark plug. He has speed, contract and energy, and he's an outfielder who changes games with legs and swagger instead of home runs. The kind of player every contender decides they desperately need once they see their offense get stale.

If Boston shops him, the bidding will be frantic. Duran doesn’t require five years of imagination –– he helps you now. And the Pirates typically don’t live in the “now.” They live in the “someday.”

By the time Cherington asks whether Boston is “motivated,” Duran will already be wearing another uniform and Pirates fans will be staring at a quote about how the price was “too high.”

...or Wilyer Abreu (OF, Boston Red Sox)

The expectation is that the Red Sox will trade one of Duran or Wilyer Abreu, now that the arrival of top prospect Roman Anthony has crowded their outfield –– and Abreu is the one that feels like Pirates fans can already see coming.

He's young. He's left-handed. He has pop in his bat. He's a good defender. He is under team control. He's everything Pittsburgh allegedly wants.

Abreu is a foundational player, so Boston's asking price won't be small. But he is exactly the kind of move the Pirates should make –– which is exactly why fans worry that they won't.

Brendan Donovan (IF/OF, St. Louis Cardinals)

If the Pirates acquire anyone from their division rivals in St. Louis, it feels like it might as well be Brendan Donovan. The Cardinals never give away players that aren’t good — they just stop paying them.

Donovan is annoying in the best way. He's always on base, he's everywhere defensively, and he's always in the lineup. He's the kind of "glue guy" that contenders love and the Pirates tend to hoard.

Donovan isn't flashy enough to scare people, but he's just reliable enough to make October miserable for opposing fans. For that reason, there will be plenty of teams calling about him, and the Pirates will likely be one of them. But fans already know they won't be the loudest ones in the room.

At most Winter Meetings, the Pirates tend to operate like a small-market think tank while everyone else operates like a big-league arms race. While other clubs add urgency, increase offers, expand deals and pull the trigger, the Pirates ask for more time, debate internal options, wait for prices to drop and watch the market close.

These four players don’t fit a “wait and see” winter –– they fit a strike-first market. And the Pirates haven’t been a strike-first team in more than a decade. If these four names move quickly, Pittsburgh fans won’t be mad because the Pirates failed. They’ll be mad because the Pirates never truly tried.

If the Pirates don't land a major offensive upgrade at the Winter Meetings this season, it will be a reminder that the dream board existed — just not for them.