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Padres’ trade deadline interest in Orioles star Jackson Holliday reeks of A.J. Preller madness

The Padres need offense, but Preller may be creating another puzzle.
Jul 7, 2026; Baltimore, Maryland, USA;  Baltimore Orioles infielder Jackson Holliday (7) tosses the ball to first base after fielding a ground ball in the second inning against the Chicago Cubs at Oriole Park at Camden Yards. Mandatory Credit: Jamie Sabau-Imagn Images
Jul 7, 2026; Baltimore, Maryland, USA; Baltimore Orioles infielder Jackson Holliday (7) tosses the ball to first base after fielding a ground ball in the second inning against the Chicago Cubs at Oriole Park at Camden Yards. Mandatory Credit: Jamie Sabau-Imagn Images | IMAGN IMAGES via Reuters Connect

We all know A.J. Preller is a madman. The Padres’ president of baseball operations treats trade deadlines like a teenager playing franchise mode with the settings turned off. Even by his standards, though, this one requires an explanation.

According to Francys Romero, the Padres have checked in with the Baltimore Orioles about second baseman Jackson Holliday. But what in the world is Preller cooking up here?

Holliday is an undeniably fascinating target. He’s 22, bats left-handed and was the first overall pick in the 2022 MLB Draft. He has also started finding his footing after a difficult introduction to the majors, batting .252 with a .743 OPS this season. We can understand why the Padres would want that kind of young, controllable talent.

A.J. Preller would need another trade to make Jackson Holliday fit

What we can’t immediately understand is where they would put him. Last we checked, Holliday doesn’t play left field. He doesn’t throw a fastball either. Those are the two clearest areas the Padres should be addressing as they attempt to force its way into the postseason.

Instead, Preller is apparently poking around another crowded section of the roster.

Second base already belongs to Jake Cronenworth. Xander Bogaerts occupies shortstop, and Manny Machado isn’t surrendering third base unless Holliday plans to wait about seven years. Baltimore gave Holliday some work at third during his injury rehab, but that experience does nothing for him in San Diego.

The cleanest alignment would place Holliday at second and move Cronenworth primarily to first. Gavin Sheets could then receive more time at DH or in left field. That technically works, but then where is Ty France going to go?

This isn’t adding a missing puzzle piece. It’s dumping another handful of pieces onto the table and trusting Preller to grab the scissors.

If the Padres are genuinely pursuing Holliday, another move almost has to follow. Cronenworth would become an obvious trade candidate, or San Diego could contemplate an even larger blockbuster involving Mason Miller. Baltimore isn’t handing over a 22-year-old former No. 1 prospect for whatever remains in the middle of the Padres’ farm system.

It would be strange since the O’s are selling. We’re sure they’d rather take on young controllable talent. The only way we see this working is with Ethan Salas on the table, especially after the Orioles just traded Adley Rutschman to the Red Sox. 

Holliday would be worth rearranging the furniture for. But Preller isn’t checking in on a clean roster fit. He’s checking in on a player who could force him to reshape the infield during the middle of a playoff race.

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