One realistic trade, one bold trade and one disastrous Pirates move at the GM Meetings

The Pittsburgh Pirates are heading into the annual MLB General Managers Meetings in Las Vegas with considerably more momentum than they've had in recent years. Unfortunately, they're also running out of time to capitalize on it.

After finishing 82-80 in 2026, the Pirates have a legitimate opportunity to build on their first winning season since 2018. But with a potential MLB lockout looming on Dec. 1, general manager Ben Cherington has an unusually narrow window to address several significant roster needs.

The uncertainty surrounding Brandon Lowe's free agency complicates matters further. Pittsburgh extended its star second baseman a $23.15 million qualifying offer, but there's a strong possibility he'll decline it in pursuit of a multiyear contract.

The GM Meetings typically produce more conversations than completed transactions. This year, however, waiting until the Winter Meetings to get serious might not be an option.

Here are three hypothetical moves the Pirates could explore in Las Vegas, ranging from realistic to ambitious to downright disastrous.

Realistic trade: Pirates acquire Zack Gelof from the Athletics

If Ben Cherington wants to address multiple offseason needs without committing to an expensive free agent, Athletics infielder Zack Gelof should be near the top of his trade wish list.

The 27-year-old enjoyed a bounce-back 2026 season, hitting .256/.322/.475 with 22 home runs, 55 RBI and 16 stolen bases in 111 games. More importantly for Pittsburgh, he hit .286 with an .885 OPS against left-handed pitching, an area where the Pirates desperately need improvement.

Gelof also offers the kind of competent defense that the Pirates haven't had much of at third base lately. After spending most of his early career at second base, he transitioned to the hot corner in 2026 and finished with nine defensive runs saved. For comparison, Nick Gonzales finished with minus-15 DRS at third base, despite hitting .303.

Acquiring Gelof would allow Pittsburgh to move Gonzales back to second base if Brandon Lowe departs in free agency, simultaneously improving the team's infield defense and adding another right-handed power threat.

There's also a financial component that makes this deal particularly appealing. Gelof is projected to earn just $2.9 million in his first year of arbitration and remains under team control through 2029.

The Athletics could reasonably demand young pitching in return, especially after finishing 2026 with a 5.51 team ERA. Pittsburgh has enough organizational depth to explore a package built around a pitching prospect such as Wilber Dotel without sacrificing one of its established major league starters.

Of course, Gelof isn't a perfect solution. His production was significantly better at Sacramento's hitter-friendly Sutter Health Park than on the road, where he hit just .215 with a .664 OPS. A move to PNC Park could expose some of those offensive limitations. Still, the Pirates would be acquiring a versatile, affordable infielder who could address two of their biggest weaknesses while remaining part of the team's plans beyond 2027.

For an organization that needs to improve without sacrificing its long-term flexibility, that's exactly the kind of trade Cherington should be exploring at the GM Meetings.

Bold trade: Pirates swing blockbuster deal for Jackson Holliday

According to recent reporting, the Baltimore Orioles are willing to listen to trade offers involving nearly everyone on their roster, including former No. 1 overall pick Jackson Holliday.

The 22-year-old hasn't lived up to his enormous expectations since debuting in 2024. He hit just .229/.300/.340 with seven home runs in 98 games in 2026, a disappointing campaign complicated by wrist injuries.

Still, there's a reason he was once considered the top prospect in baseball. Holliday's combination of offensive upside, athleticism and defensive versatility still makes him an intriguing long-term investment. And with Brandon Lowe potentially departing in free agency, the Pirates could offer him a clear opportunity to establish himself as their everyday second baseman.

Imagine a middle infield featuring Holliday and Konnor Griffin, Pittsburgh's own former top-ranked prospect, for the foreseeable future.

Of course, Baltimore wouldn't surrender Holliday cheaply simply because he's struggled in the majors. The Orioles reportedly want starting pitching and outfield help, two areas where the Pirates have potential trade assets. A package involving a controllable major league pitcher, plus additional prospect capital, could at least provide the framework for an ambitious conversation.

There's still considerable risk for Pittsburgh. Holliday hasn't demonstrated that he can consistently produce at the major league level, meaning the Pirates would be surrendering valuable pitching depth for potential rather than proven production. But that's also what makes the possibility so intriguing.

Cherington has spent years emphasizing the importance of acquiring young, controllable talent with considerable upside. Holliday fits that philosophy almost perfectly. The Pirates would be be betting that a former No. 1 overall pick could become a foundational piece alongside Griffin, Paul Skenes and the rest of their emerging young core.

It's the kind of high-risk, high-reward move that could dramatically reshape Pittsburgh's future. And with Baltimore apparently open for business, there's no harm in making the call.

Disastrous move: Trade Jared Jones for a short-term offensive fix

The Pirates absolutely need another right-handed power bat. That doesn't mean they should sacrifice one of their most valuable young pitchers to acquire one.

Consider, for example, a hypothetical trade involving Jared Jones and Cleveland Guardians outfielder Jo Adell. Adell's offensive profile makes him an understandable target. He hit 23 home runs in 2026 and has demonstrated an ability to punish left-handed pitching — something Pittsburgh's lineup desperately needs after another disappointing season against southpaws.

But Adell also hit just .240 with a .298 OBP and a .699 OPS overall. His aggressive approach and swing-and-miss tendencies raise questions about how much he would improve the Pirates' offensive consistency. Even more importantly, he's eligible for free agency following the 2027 season.

Jones, meanwhile, remains one of the organization's most valuable young building blocks. He finished September with a 0.93 ERA and 40 strikeouts in 29 innings, offering another reminder of his considerable upside. Trading that kind of controllable pitching talent for one season of a flawed offensive player would be an enormous mistake.

Pittsburgh has spent years assembling an impressive collection of young pitchers. Trading away its most promising arms for short-term offensive solutions would undermine the very foundation that helped the organization become competitive again. And with Skenes moving closer to his own increasingly expensive arbitration years, inexpensive, controllable pitching should only become more valuable.

The Pirates have enough roster flexibility to entertain creative trades this offseason. What they can't afford is another round of short-sighted decisions disguised as progress.

Cherington doesn't necessarily need to leave Las Vegas with a blockbuster deal, but he should leave with a clear understanding of which players can help Pittsburgh take the next step, which assets he's willing to move and which ones are too important to sacrifice. With December's potential labor stoppage approaching, the clock is already ticking.

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