MLB’s No. 1 prospect Jackson Holliday on his rise, Orioles’ future, viral hotel story

Jackson Holliday is wise beyond his years, even if he does not look it. 

The 19-year-old phenom is the current No. 1 overall prospect in baseball, and is already in Triple-A just a little over a year after being picked first overall in the 2022 MLB Draft by the Baltimore Orioles. For good reason, too — the man has raked at every single level of professional baseball he has appeared in. He even hit his first Triple-A home run Thursday after our exclusive interview on “Flippin’ Bats.”

Holliday’s youthful appearance masks his incredible talent and the baseball IQ honed under his father Matt Holliday, a seven-time All-Star with the Colorado Rockies and St. Louis Cardinals. In speaking with him, it was easy to tell that the younger Holliday had learned a lot from growing up around MLB clubhouses thanks to his father and now gets to apply those lessons daily.

Despite the fact that he will be one of the youngest players in a very youthful (and very, very good) Orioles core, he already has more up-close exposure to the MLB playoffs than most of his teammates.

“Growing up in baseball and my dad being with the Cardinals, they were in the postseason every single year,” Holliday told me. “All I know is postseason baseball and good teams.”

Of course, Holliday’s youth can still pose issues sometimes, just like it did when he attempted to check into a hotel in my old college town of Norfolk, Va. after being called up to the Norfolk Tides, Baltimore’s Triple-A affiliate.

“We had everything situated, and they’re like, ‘Can we see your ID? … You can’t get a room unless you’re 21. You can [reserve] a room, but you can’t check in if you’re not 21.’ Makes sense. So the guy was like, ‘Well, you’re not old enough.'”

Jackson asked the hotel staffer whether he could have his mother check him in. The hotel staffer responded, “Sure, is your mother nearby?”

Leslee Holliday was back home in Stillwater, Oklahoma.

“I’m like, ‘Well, I just got called up to play baseball on with the Orioles,’ and he’s like, ‘All right, here’s the room,'” Jackson Holliday recalled. “It was pretty funny. Kind of a really long day. “

The story quickly went viral when Holliday told a local reporter the next day about his ordeal.

“It’s alright,” Holliday told me. “They were very, very nice and they hooked us up, so it was great.”

Baltimore Orioles’ Jackson Holliday on the transition from high school to the pros

On the field, meanwhile, Holliday is still honing his skills as a shortstop and at the plate. Some of his favorite players growing up — besides his father — were Troy Tulowitzki and Nolan Arenado, and Holliday more recently has modeled parts of his game after current star shortstops like Trea Turner, Bo Bichette and Corey Seager. He even worked out with Cody Bellinger last offseason. 

“He loves baseball and that’s all we wanted to talk about,” Holliday said. “That was cool for me to see, and it’s definitely helped me this year being able to handle myself on and off the field.”

Like the vast majority of minor-league prospects (myself very much included), Holliday initially had some bumps in adjusting to professional baseball, even as a top overall draft pick. But he has definitely made the adjustment now, as evidenced by a .322/.443/.505 slash line across four (!!!) levels in the minors this season. 

Holliday says that his struggles on the showcase circuit against many other future pros before his senior year of high school helped him prepare, as did some early adjustments once he arrived at the Orioles’ facility after he was drafted.

“Challenging myself off the field in practice has been very helpful for me,” Holliday said. “When I got to Low-A last year, being able to control the zone and not swing at balls, and whenever I did get into hitters counts, being able to capitalize was very helpful.”

Soon, Holliday will be in the major leagues — if not this season, then definitely sometime early in 2024 as long as he stays healthy. Though the Orioles already have plenty of young stars such as Adley Rutschman and Gunnar Henderson — whom Holliday has nothing but praise for both on and off the field — he is still a No. 1 overall pick, and must deal with the pressure that comes along with that.

“I feel like I’ve done a pretty good job of just going out there and playing baseball,” Holliday said. “One of my one of our buddies back home [told me], ‘Pressure is a privilege.’ … If you have pressure, you must be doing something right. So that’s kind of how I’ve gone about it. Luckily, I’m in an organization with a bunch of really talented guys, and a lot of guys that I get along with, so it makes it fun to be able to come out here and play.”

Baseball fans are also going to get the privilege of watching Holliday be very, very good for a very long time. I’m so excited to watch him in the big leagues, where he will join an Orioles team that looks like it should be in playoff contention for the next several seasons. 

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Holliday understands the expectations awaiting him in the majors — and he has lofty ones of his own. He wants to win gold gloves and would like to earn a batting average title as well like his father did in 2007. But right now, he is aiming for the day when he is no longer baseball’s top prospect, but a bona fide big leaguer on a World Series hopeful.

“I’m trying to make it up to the big leagues as fast as possible and help the Orioles win championships,” Holliday said. “That’s the goal, to help the Orioles win a World Series and have a long, long career.”

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