Meet the 1st of a new generation of baseball Hollidays

July 17th, 2022

The Orioles selected Jackson Holiday with the No. 1 overall pick in the 2022 Draft. Here's a deeper look at Holliday that was first published on in the weeks leading up to the Draft.

In case you’re wondering, it feels pretty good to hit .685. Jackson Holiday can attest.

“It’s pretty fun,” he said with a laugh. “It’s pretty fun.”

Holliday, 18, is probably best known as the son of seven-time big league All-Star Matt Holliday, but he’s a lot more than that. He’s one of the top prospects in the 2022 Draft. He’s the product of a long line of baseball lifers, and possibly the first one of a new wave of Hollidays in baseball. And he’s a complete player.

That last part is important to the shortstop out of Stillwater (Okla.) High School, who has a commitment to attend Oklahoma State in the fall. Holliday is a two-time Rawlings High School Gold Glove winner, along with being one of the most skilled offensive players in this class. He was also the Gatorade Player of the Year for Oklahoma and Baseball America’s National High School Player of the Year after posting that .685 batting average and setting a national high school record with 89 hits.

Courtesy of the Holliday family

Holliday's biggest highlight, though, came much closer to home. In fact, about 50 feet to his right this past spring. For the first time in their young lives, Jackson and his younger brother Ethan got to be teammates. Jackson batted second and manned shortstop for Stillwater, with Ethan playing third base and batting in the three-hole.

Out of all the accolades, it was that opportunity that stood out most.

“That was by far my favorite memory,” Holliday said. “Being able to play with [Ethan]. This is the first time, so it was really neat.”

It’s that spirit that stands out most to his dad. The Hollidays are a baseball family like few others. Grandfather Tom coached at Oklahoma State for 26 years. Uncle Josh has helmed the program since 2013. And Matt, you know. Matt emphasizes that he never had to push Jackson to play ball. He loved it almost from Day 1.

“I always wanted him to be as natural as possible,” said Matt. “When he was a kid I wanted to pitch to him and learn to be natural and not really think about mechanics. As he got older and started to understand and mature, that we could work a little bit more on mechanics.”

Courtesy of the Holliday family

Jackson has spent his whole life around baseball. Matt always made a point to have his kids around the clubhouse as much as possible, and as the oldest, Jackson was most in position to soak up knowledge and learn by observation. He points to Nolan Arenado, during his dad’s last year in the big leagues, as a particular influence.

Perhaps as a result of that observation, perhaps from natural talent, Holliday has always been a skilled baseball player. Matt notes that even in elementary school, long before mechanics were something to think about, his son had sound swing mechanics.

Coming into this year, though, Holliday was not a tip-top Draft prospect. That’s because, though he had a sweet left-handed swing and smooth actions at shortstop, he didn’t have the power to come with it. But over the past year or so, Holliday has grown into his body some, developed more strength and -- look at that -- the power came.

That turned him from a player thinking about Oklahoma State to one thinking about playing pro ball right away.

“I was just trying to improve,” he said. “I cleaned up my swing and I got stronger. I always felt like I had the skills to be able to do this, but I just needed to get stronger and put it all together. So me and my dad worked a lot, and it all paid off.”

Courtesy of the Holliday family

Even if Holliday doesn’t head to OSU, though, he’ll likely always return home to Stillwater. After years of moving around, Matt, his wife, Leslee, and their four kids moved back to the family’s home turf in 2018. Wherever their baseball family tree may grow, there’s no doubt where its roots lie.

“It’s awesome to be able to be in Stillwater and have everyone in my family be there and support me,” Holliday said. “They’re all able to come to my high school games. They’re always there for me. They love baseball as much as I do, and they’re always rooting me on and cheering for me. It’s great.”