The Orioles selected shortstop Jackson Holliday out of Stillwater High School (Okla.) with the No. 1 overall pick of the 2023 MLB Draft. The son of seven-time All-Star Matt Holliday, Jackson began his professional career with stints in the Florida Complex League and at Low-A Delmarva in 2022. The 6-foot, 185-pound shortstop hit .297/.489/.422 between the two stops and returned to Salisbury to begin the 2023 season.
Holliday hit .396/.522/.660 in 16 games with the Shorebirds to start the season before earning a promotion to High-A Aberdeen April 24. So far with the IronBirds, he’s slashing .321/.463/.536 with 16 extra-base hits and 24 RBIs in 39 games entering play June 14.
Delmarva manager Felipe Alou Jr. and Stillwater baseball coach Jimmy Harris chatted with PressBox about the 19-year-old Holliday.
PressBox: What makes Holliday special? What sets him apart?
Felipe Alou Jr.: When we got Jackson, especially when I got him up in Delmarva, right away you could pick up that we made the right choice in regards of who we drafted first. First of all, where he was coming from — baseball family, this kid’s pretty mature, goes about his business on a daily basis. He’s very approachable, has no issues coming to you or you going to him for stuff and the teaching part — and then the tools. I had him at 18 years old for a little bit, a few weeks, and very mature for an 18-year-old kid. Like I said, the way he goes about his daily stuff, the workouts, the games, he’s eager to compete. During practice on the defensive side trying to compete with other teammates, all this kind of stuff is what sets him apart.
PB: How did you see Holliday get better under your watch?
Jimmy Harris: He always did things right. He knew at an early age who he was. He knew what his last name was. He knows what comes with that. So one of the things that he did really well was he led the team by actions. He led the team by example. He led by, “I’m not going to tell you to run. I’m just going to run by you really fast and hustle out to my position and you’re going to know that you’re supposed to run out there.” … And then last year, he turned into the coach. He led by example. One of the best things I can tell you is he just got back from winning the gold medal with Team USA. We’re running sprints and he’s Jackson Holliday. I’m thinking, “OK, he’s going to run hard, but whatever.”
Well, he made it a point to win every race. He made it a point to fly around, and he made it a point when I said something to him and his dad. He said, “That’s what we’re going to do.” He made it a point his senior year that he knew he was the best player and the best player was going to do the right thing, which made my job way easy. He made sure he always wore the right stuff. He made sure he was always on time. He made sure of everything. And then along the way, he would coach people. There would be times he would stop taking ground balls from me and he would walk from position to position and work with some of the younger guys and talk to them. Those are some of the cool things that he did that I thought were pretty neat.
PB: What kind of relationship did you develop with Holliday?
FA: I honestly think like most of the other kids, I wanted to make sure he felt comfortable right from the get-go. He’s a kid that I can relate to because of where my family comes from, so I kind of made him aware of that, just wanted him to be himself and play the game. I wasn’t a first pick, first-rounder, but I would say I relate to that upbringing of coming from a baseball family. This kid goes about his business every day. There’s not a whole lot of … hype within him. There’s just ready-to-come-to-the-ballpark and do his thing and improve.
PB: What’s your favorite Holliday story?
JH: We’re in the regional tournament and we’re playing Owasso … and Jackson takes us into extra innings. And then we go into the extra inning and he hits a home run. We’re ahead at that point. We might win the game. You know his numbers. He had one of the most unbelievable high school seasons that anyone’s had at that level. He played so well. … He hits the home run, and he kind of stood there for a second and watched it. Jackson’s not one of those guys. He’s not a bat-flipper. He’s not going to do that. But he watched it. He hustled around the bases like he normally does, and he got really excited.
He comes into the dugout and he’s yelling. I didn’t get to see it, but I got to see it from across the way. My most fun memory of him was because of how excited he got with his team. My daughter was a manager. She graduated in the same class with Jackson. She was telling me about how cool that was, how he just came in there and was so excited. He’s hugging everyone. He’s high-fiving everyone. “Let’s go!” He’s doing that kind of stuff. That was pretty cool.
PB: Was there a moment when you realized Holliday was going to be special?
JH: He had just finished eighth grade. He came and played on our high school team [during a summer tournament]. Everyone else is usually probably going to be sophomores, going to be juniors or maybe going to be seniors, and he’s going to be a freshman. He played shortstop and he led our team in hitting and he didn’t strike out one time. I thought, “Wow, that’s pretty impressive.” Not that we played the most awesome schedule or anything, but everyone else was striking out. They struck out at least one time. This kid never struck out. I mean, that was pretty cool. You saw right then, and he was a little, bitty guy. But you saw right then there was something special in this kid.
PB: Where might Holliday need to improve to reach his ceiling? What challenges may he run into?
JH: The challenges looking ahead, I met with Matt Holliday and Mike Gundy. Mike Gundy’s the head football coach at Oklahoma State, and his boy Gage played for us. We had a team meeting where we got to talk to those two guys, and it was incredible. But one of the questions I asked Matt was, “How did Jackson play his senior year, and how did he play where it looked effortless? How did he handle the pressure? How did he handle all the things that [came] his way?” And it was funny because his answer was, “Man, I don’t know. I don’t know how he did it.” Because that’s a question that we keep asking: How did this young man keep handling the pressure and all this? And the best thing that we could come up with is Jackson loves competition and that little bit of being in the limelight, of “I’m going to show you guys I have an opportunity to do whatever,” he enjoys those moments.
Photo Credit: Patrick Cavey
Originally published April 19, 2023. Updated June 14.