Baltimore Orioles second baseman Jackson Holliday might not be the most well-known figure among baseball fans, but those around the sport are very familiar with the 2022 No. 1 pick.
Holliday’s father, Matt, was an All-Star outfielder who played for four teams over 15 seasons. His younger brother, Ethan, is an infielder in the Rockies’ farm system, and his uncle, Josh, is the head baseball coach at Oklahoma State.
Then, there are those who Holliday crossed paths with while training at Club Nemesis, an Arizona-based baseball performance center launched by Cubs third baseman Alex Bregman. It’s no wonder the contact list in his phone continues to grow rapidly.
“It’s fun to be in baseball, to know people in baseball,” Holliday told the Orioles’ Jake Rill. “Probably growing up in a college town also helps. I don’t know a number or even have a clue. It’s fun to get to know guys you play against, too. It’s kind of just a community.”
That sense of “community,” as Holliday put it, might prove vital if the Orioles explore trading him this offseason.
Could the Baltimore Orioles trade second baseman Jackson Holliday?

The Orioles are at a crossroads, and they have two realistic options over the next few months: the first being to buckle down and keep what remains of their young core. Adley Rutschman is already gone, but Holliday, Gunnar Henderson, and Colton Cowser are still around. Let’s also not forget that Baltimore signed Pete Alonso last winter, and he recently crossed the 30-homer threshold yet again.
Alternatively, Baltimore could hit the reset button, which would almost certainly involve trading Henderson. Third baseman Coby Mayo turns 25 in December, and he’s under team control through 2031, both of which could appeal to contenders seeking corner infield help; the 2020 fourth-round pick spent most of last year as the Orioles’ starting first baseman.
Holliday doesn’t turn 23 until December, and he’s under team control through 2030. Barring a remarkable return, there is no reason for the Orioles to trade Holliday yet, which made it all the more surprising when he was reportedly discussed at the deadline. It remains unclear whether those conversations ended within 30 seconds.
Teams have realized that they don’t always need to give up their marquee prospects via trade. Look no further than the Tigers’ lackluster return for Tarik Skubal, and the argument about him being a rental only goes so far when you remember that he’s a two-time defending Cy Young winner and arguably the sport’s best starting pitcher.

Holliday has provided the Orioles with a .677 OPS and 0.5 bWAR, though his walk rate has skyrocketed from 8.6% to 12.4%. The talent is there, but that likely wouldn’t be enough to warrant a considerable trade package. Henderson is easily the Orioles’ most valuable trade chip, and Cowser profiles as a buy-high candidate for a contender like the Yankees or Phillies.
If the Orioles did make Holliday available, it sounds like a significant number of players leaguewide might be willing to vouch for him. However, there’s one part of his lifestyle he’d potentially need to change in hopes of winning over new teammates.
“A lot of baseball guys. I’m probably the worst person ever at texting,” Holliday quipped.
