The Pirates have a clear problem on the infield, and it’s the kind that could push them toward a major swing at the GM Meetings. Brandon Lowe may be headed for free agency, Jared Triolo hasn’t hit enough to lock down more than a utility role, and Nick Gonzales hasn’t defended well enough to be trusted every day. That leaves Pittsburgh with a messy picture at second and third base.
Keeping Lowe would solve a lot of that, but that path looks shaky now that he can talk to contenders with far more money to spend. The free-agent market doesn’t offer much help beyond that, which is why a trade may be the better route if the Pirates want a real answer.
That brings Baltimore into the conversation. The Orioles are in the middle of a possible fire sale, and their roster is loaded with young infield talent. One name stands out above the rest: Jackson Holliday, the 2022 No. 1 overall pick and once the top prospect in baseball.
Holliday hasn’t taken off at the big-league level yet, but the talent is still obvious. Over three seasons and 307 career games, he has posted an 86 wRC+ with 29 home runs and 29 steals. With Baltimore still hunting for pitching help - and now even more desperate after Trevor Rogers reached the open market - Holliday looks like a real trade candidate this offseason.
The Orioles are reportedly open to trades for any player except for Pete Alonso as they look to improve their starting rotation and outfield depth. #MLBNHotStove pic.twitter.com/Pr7kMzdlHo
- MLB Network (@MLBNetwork) November 4, 2026
If the Pirates want to get serious, they have the kind of arm talent Baltimore wants. Paul Skenes is not part of the conversation, but Bubba Chandler could be the sort of young, controllable starter that gets the Orioles’ attention. Both are pre-arb players with upside, and both would fit the kind of deal Baltimore is likely to pursue.
It would be a steep price, no question. But Holliday is also more than a full year younger than Chandler and tore through the minors as a teenager. Put him next to Konnor Griffin, and Pittsburgh would suddenly have one of the most intriguing double-play combinations in the game.
If the Pirates want to replace Lowe with someone who matches or even tops his talent at second base, this is the kind of opportunity they may not do better than. The only question is whether they’re willing to pay what it takes.
In Other News...
Pirates Fans Need To Be Honest About Konnor Griffins ROY Case
Konnor Griffin gave Pirates fans plenty to dream on in his first full look at the big leagues, flashing the kind of defensive ability and long-term upside that can make a young player feel bigger than the box score. Even so, the National League Rookie of the Year race ended with Griffin on the outside of the finalist group, while Cincinnatis Sal Stewart took home the award after a season that was impossible to ignore from a durability and production standpoint.
Stewart was on the field every day and led rookies in several offensive categories, which gave his case a straightforward edge even against Griffins stronger bWAR in fewer games. For Pittsburgh, the takeaway is less about a snub than about the shape of Griffins season: the talent was obvious, but the interruptions kept him from building the kind of complete rsum that tends to sway awards voters. [Read more 🡒]
Pirates Draft Vision Is Getting A Very Different Kind Of Leader
The Pirates draft room has a new voice steering the process, and it comes from a different lane than the one many fans might expect. Justin Newman was promoted in October to oversee amateur scouting and player evaluation, putting him in charge of a group that has to balance eyes-on-the-ground scouting with the longer-term demands of building a pipeline that can actually sustain success.
Newman has been with the organization since 2017, and his path through the front office has given him a reputation for thinking carefully about how decisions get made, not just who gets picked. He has stressed the value of traditional scouts in that mix, while also focusing on leadership and process improvement as the Pirates look for a draft approach that can hold up year after year. [Read more 🡒]
Pirates Face A Brandon Lowe Race They Can't Afford To Lose
Brandon Lowes first trip into free agency has quickly become one of the more important offseason tests for the Pirates, who would clearly like to keep the veteran in the fold. He has already received a qualifying offer, giving both sides a firm early marker as the club weighs how aggressive it wants to be in trying to bring him back.
Pittsburgh is exploring a few different ways to structure a deal, including longer-term possibilities that could give Lowe flexibility while helping the team manage the money. The wrinkle is the larger labor picture, since ongoing collective bargaining talks could affect when clubs and players are willing to push forward on new contracts, leaving this one with more moving parts than most. [Read more 🡒]