Unique Skill, Pro Approach Help Orioles’ Holliday Become MLB’s Top Prospect

Pat Pickens
Last Updated: Jul 31, 2023

BRIDGEWATER, N.J.Jackson Holliday set a goal for himself to reach Double-A by the end of the 2023 baseball season.

With the way he is tearing up the Eastern League, Holliday may not be there long.

The 19-year-old and top pick of the 2022 MLB Draft has emerged as the No. 1 overall prospect in baseball, according to MLB Pipeline and Baseball America.

Whenever he reaches the majors, he has all the tools to become the face of the loaded Baltimore Orioles.

Holliday won’t turn 20 until Dec. 4 but is almost certainly closer to his big-league debut than his first legal drink. He has surged through the Orioles’ minor-league system this season, starting in Single-A Delmarva, with a 10-week stop in High-A Aberdeen, before getting the call to the Orioles’ Double-A affiliate in Bowie on July 14.

“It’s kind of crazy to think about what I’ve accomplished in a year,” Holliday told reporters before one of Bowie’s games against the Somerset Patriots last week.

“This was my goal, to make Double-A by the end of this year. Now I’m here, and I’m very fortunate to be in this position. This is what I set out to do.”

Holliday has showcased his 65 overall grade and 60-grade hitting by slashing .334/.458/.523 across all minor-league levels this year as of July 31.

He earned a spot in the MLB Futures Game during the All-Star break, then was crowned the top prospect ahead of Elly De La Cruz, who had lit the baseball world on fire for the Cincinnati Reds before he graduated from prospect status.

“The first thing that jumps off is the tools: his ability to run, catch, hit, throw,” Bowie manager Kyle Moore told The Game Day Baseball. “To execute some of the things [he] can execute in the ballgame is probably unlike anything I’ve ever seen.”

Holliday hasn’t slowed down after his promotion to Double-A either, slashing .357/.400/.524 in the Eastern League as of July 31. Scouts and others around baseball have raved about his one-of-a-kind demeanor, which has aided his progression through the ranks.

“He’s been awesome,” Bowie hitting coach Sherman Johnson told The Game Day Baseball. “The ability to learn, the eagerness to work, it’s all there. Obviously, it helps that he’s a really good player. At age 19, you don’t see it often, if ever.”

A Professional Approach

Holliday can have an impact on every facet of the game. Aside from his elite hitting skills, he’s a plus defender, who makes extraordinary plays look effortless, and has 20 stolen bases across all levels this season as of July 31.

“I’m someone who likes to impact the game in all aspects,” Holliday said. “I like to steal bases. I like to play defense.”

With that said, Holliday is most renowned for his offensive capabilities. Though it’s clear he needs to bulk up — he has eight homers across all levels as of July 31 but intends to get stronger this offseason to improve his power numbers — Holliday rarely chases pitches and is exceptionally gifted at working counts and making hard contact when he gets his pitch.

“He’s always trying to stay in the big part of the field, and he’s really good at hitting the ball to the opposite field,” Johnson said. “He’s 19, and he’s taking 3-1 off-speed pitches and lining them to the middle of the field when some of our guys that have played in college are like ‘3-1, and I’m only looking for a fastball.’

“He’s already adjustable. He’s not just looking for one pitch. He’s looking in his zone and looking to do damage.”

He also hasn’t been affected by the fanfare, and the heat of being baseball’s top prospect isn’t likely to faze him. He spent most of his young life in big-league clubhouses as the son of Matt Holliday, a seven-time MLB All-Star and four-time Silver Slugger.

However, he stepped into his own spotlight when the family moved to Stillwater, Okla. after Matt retired in 2018.

“He started playing for us between his eighth-grade and ninth-grade year, which is a pretty big deal considering it was our varsity program,” said Billy Jones, one of Holliday’s coaches at Stillwater High School. “He played with us that summer, and he led the team in hitting.

“He looked like an eighth grader, physically, so that was pretty impressive.”

Holliday batted .685 with 17 homers and a 2.141 OPS his senior year at Stillwater High School, earning Gatorade state player-of-the-year honors while attracting dozens of scouts to both games and practice all season.

“Every day, he was even-keeled; not too high, not too low,” Jones said.

“There are some days where there were closer to 40 scouts just hanging out at our baseball field watching him, and the coaches were amazed just how unaffected he seemed by it because he’s so focused on what he’s doing, and it doesn’t matter that they’re there.

“He was a pro in everything he did. His demeanor, his work ethic. At practice, he was the same guy he was on game day.”

Holliday’s ‘It’ Factor

Holliday committed to play at Oklahoma State for his uncle Josh but passed on college when the Orioles selected him first in the 2022 MLB Draft. He became the 26th high-school player chosen first overall and the first since Royce Lewis was selected by the Minnesota Twins in 2017.

Unsurprisingly, he’s shown no ill effects of eschewing college thanks to his wise-beyond-his-years maturity level on the field and off. Even though he’s been in Bowie less than a month, he’s already become a leader, teaching valuable lessons to some of his older teammates.

“One thing I’ve learned from him is how to carry yourself on and off the field, no matter what,” Bowie infielder/outfielder Billy Cook said. “You see the attention that he gets, and it doesn’t let him affect his performance. It doesn’t let him affect his relationships at all. That’s a hard thing to do, separating baseball from your life outside the clubhouse.”

Fans come out in droves to see Holliday and snag a piece of history. Holliday has become renowned for his patience and willingness to sign autographs before and after games, both in Bowie and on the road, as he showcased by signing for road fans before the lone game in Somerset on Wednesday — he missed the rest of the series due to an undisclosed illness.

“He gets that fans are super-important to our game and growing our game,” Moore said.

“I’m sure he gets that from his dad. He comes from a great family who probably instilled some really good morals in him and things that you really can’t coach.”

Aside from “getting it,” Holliday has also showcased a certain je ne sais quoi of a captain or face of the franchise. His first Double-A home run was a game-tying shot in the seventh inning of Bowie’s 8-5 win against Harrisburg — only after also making a critical defensive play the inning prior.

“I think there’s certainly an ‘it’ factor and a lot of it is his ability to process the game mentally so fast,” Moore said.

“His mind works a couple of plays ahead of the ballgame, and I think that’s the ‘it’ factor you see because a lot of kids have tools, … but not a lot of guys can think two or three plays ahead of the game like Jackson does.”

Baltimore’s Golden Era

The Orioles lead the American League East and hold the best record in the AL as of July 31. They also have the seventh-youngest roster in the majors (27.7), according to ESPN, and it is full of high-skill, high-character players.

“We haven’t only drafted well, we’ve drafted really high-makeup guys,” Moore said. “It’s just a great time to be an Oriole.”

It’s still possible Holliday will join Colton Cowser, Jordan Westburg, and Grayson Rodriguez as prospects who made their major-league debut in 2023 in Baltimore.

“I wouldn’t rule it out, but I don’t rule out anything,” Orioles GM Mike Elias said at a news conference, according to the Baltimore Sun. “One step at a time. He’s in Double-A. He was in high school a year ago.”

But the organization doesn’t intend to rush Holliday’s progression, despite his quick ascent through the ranks.

“When they deem Jackson is ready to go play in the big leagues, I’m sure he’ll be there,” Johnson said. “I can’t speak if he’s ready or not. What I do know is he’s learning at a really high level, and the play speaks for itself.”

Moore, who has coached or managed almost every Orioles player in his 15 seasons with the organization, compared Holliday to another of Baltimore’s exceptional young stars, All-Star catcher Adley Rutschman.

“They just have this unbelievable charisma, this calmness that big moments and big stages and a lot of chaos doesn’t affect them,” Moore said.

“I think that’s because of their tools and their physical ability.”

Holliday will almost certainly become a core member of that group, perhaps as soon as next season. Whenever it happens, he’ll join those listed above and preseason AL Rookie of the Year favorite Gunnar Henderson for what should be a golden era of Orioles baseball.

“It’s very exciting,” Holliday said. “I’m very, very blessed to be a part of such an amazing organization, especially right now with all this young talent and a great group of guys. It’s very exciting to be a part of.”


Pat Pickens

Pat Pickens is a seasoned sportswriter who has covered the NHL since 2013 for various websites, including The New York Times, NHL.com, Sportsnet.ca, USA Today, the Associated Press and many others. His debut book, titled "The Whalers" about the history of the NHL's Hartford Whalers, was released in October 2021.

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