Those watching Jackson Holliday become the Orioles’ first overall draft pick witnessed something Stillwater baseball coach Jimmy Harris saw 29 times this spring, once after each of the shortstop’s doubles in his record-setting high school season.
With his parents to his right and his girlfriend and siblings to his left as his name was announced by Major League Baseball commissioner Rob Manfred on Sunday night, Holliday let out a smile and began to clap.
“When they win a World Series someday and he’s out there,” said his mother, Leslee, “that’s the same look you’re gonna get.”
His father, former MLB All-Star Matt Holliday, has loved rewatching the broadcast video in the days since Jackson joined Ken Griffey Jr. as the only sons of major leaguers to be picked first overall. The responses of each of his and Leslee’s four children align with their personalities, Matt said, comparing Jackson’s relative stoicism — somewhat interrupted when Matt wrapped his left arm around him — to how Ethan, their second oldest and a potential top prospect in the 2025 MLB draft, dropped his jaw and threw his arms in the air.
Matt orchestrated the moment. His training with Jackson in many ways led to the selection, but agent Scott Boras had called him with the news about 30 seconds before it was announced. Matt chose to hold it in, figuring his loved ones’ natural reactions would be better for television.
Father and son had worked for months, not to be Baltimore’s first pick, but simply the best player Jackson could. The Orioles did not have Jackson, 18, in consideration for No. 1 when their scouting department met in the winter to discuss options, but he skyrocketed to become their choice with his skill and the same demeanor he displayed after his selection, one that resulted in an agreed-upon franchise-record signing bonus of $8.19 million.
His parents and coaches described a “steady,” “even-keeled” and “well-balanced” player and person who is prepared for what awaits him on his journey from Stillwater, Oklahoma, to Camden Yards.
“He’s gonna give you everything he has,” Harris said. “I don’t know how long that’s gonna be, but there’s gonna be one day where that dude is leading the city of Baltimore.”
A quiet standout
As Jason Maxwell watched the first handful of draftees come off the board Sunday, tears formed in his eyes. The summer before, he coached four of the top five picks for USA Baseball’s 18-and-under national team.
Holliday went first, with outfielder Druw Jones behind him to the Arizona Diamondbacks, infielder Termarr Johnson fourth to the Pittsburgh Pirates and outfielder Elijah Green next to the Washington Nationals. The Orioles viewed each as a possibility atop the draft.
“I’ve spent more time talking about those four guys in the last month than my own two children,” Maxwell quipped.
Holliday was the quietest, Maxwell said, speaking clearly when spoken to but allowing his play at shortstop to do much of the talking. The other three spent that summer perceived as candidates to go first in the 2022 draft out of high school. Holliday was seen as a skilled, early-round talent, but questions about his size in particular kept him from being projected near the top of the first round.
Still, he impressed Maxwell with his fundamentally sound game and his flowing blonde hair.
“He observes and watches, and then he’s that assassin on the field,” Maxwell said. “He’s going to have all your girlfriends drooling over him because he’s the best-looking kid on the planet, and then he’s gonna go out and get three hits against you. Pick your poison.”
Holliday returned from the summer circuit with an understanding of where his game could improve, needing to be stronger, faster and capable of hitting the ball to all fields. He worked with his father, a seven-time All-Star during a 15-year major league career, on each aspect.
Jackson’s swing was the stuff of legend when he was a toddler. All three Holliday boys naturally bat left-handed, confounding Matt, among the top right-handed hitters of his generation. Born months before Matt’s major league debut, Jackson spent much of his life following his dad around clubhouses, getting an early understanding of what was required to have a locker in one.
“I’ve gotten to see what it takes to get to the major leagues,” Jackson said, “and how players, even when they’re at the top of their game, how hard they still work to maintain it.”
His senior year at Stillwater was an education in what it takes physically. Jackson took online classes exclusively but still woke up to get breakfast with Ethan and lift weights with the rest of the Pioneer baseball team at 7 a.m.
“There’s no reason for him to get up at 7 and come lift with us when he’s not going to school like everyone else,” Harris said. “But that’s the part that made it so cool, that that dude got up. He was there every day.”
He then headed home, taking care of his virtual schooling before going to Oklahoma State’s O’Brate Stadium. Before signing with the Orioles, Jackson was bound for OSU, where his dad is an assistant on his uncle’s staff. His grandfather and great uncle have also coached there.
He worked out and trained with his dad and the Cowboys, headed back to practice with his Stillwater teammates, then watched TV, took a swim and spent time with family before going to bed to wake up early again the next day.
“We just tried to grow steadily,” Jackson said. “I would try to take advantage of everything I could to hopefully be in this position.
“I’m someone who likes to be good at kind of everything. I don’t want to have a weakness, so trying to just grow myself as a person and as a player was something that was very important.”
The first time Orioles executive vice president and general manager Mike Elias watched Jackson this spring, he struck out three times in four hitless at-bats. His first strikeout of the season came a week earlier, in his 104th plate appearance. He ended the year with seven total.
When Stillwater’s season began, Jackson’s physical improvements showed immediately, setting off what Elias called “a fire alarm in the scouting industry.” A four-game tournament in Arizona came amid spring training, with scouts from several major league teams, including the Orioles, watching. They saw Jackson go 11-for-16 with seven doubles and a home run.
The reports the Orioles got from their evaluators there lined up with those they received from Midwest area scouts Ken Guthrie and Jim Richardson, describing a prospect whose ceiling grew as much as he had.
“The one thing we always are prepared to do is keep an open mind,” Orioles director of draft operations Brad Ciolek said. “The moment those reports came in, it was basically a full pivot.
“We were really just blown away about the total, complete player he had turned into.”
Elias’ attendance at that mid-April game against Bixby told the Hollidays that Jackson going first overall was possible. It marked one of only three outings he went without a hit as he set a national record with 89 in 40 games, batting .685 with 17 home runs, a .749 on-base percentage and a 1.392 slugging percentage while stealing 30 bases without being caught. Since his freshman year, Jackson has grown about 4 inches and 30 pounds, now listed at 6-foot-1 and 175 pounds.
“When you get a little bit older, it’s easier to start putting on some man strength,” Matt said. “He had been kind of a late developer as far as hair on his face and really turning into a man as far as muscles go.
“The transition from young kid to a young man really took his game to the next level.”
As much as the Orioles valued Jackson as a player, it stuck with Leslee how interested they were in him as a person, from the relationship the family built with Guthrie up to Elias. Baltimore’s general manager, she said, asked questions that were “unique,” focused on sincerely getting to know Jackson rather than generalities about his likes and dislikes.
“I think character mattered to Mr. Elias,” Leslee said. “He realizes that at the end of the day, you want to hire someone that’s going to honor the team and work hard and compete, and you don’t have to doubt Jackson’s ability to show up at the field every day and give it all he has. I appreciated that they took the time to get to know Jackson as a man.
“Whether they were number one or number whatever, he just felt there was an immediate, ‘Oh, I wanted to be with them.’”
That connection meant that as Sunday night neared, with Jackson’s future destination about to be revealed, the family hoped for Baltimore because it meant he was not only the No. 1 pick, but also going to an organization that appreciated the sixth tool that was his personality.
Among the questions Elias asked Jackson was how he handled failure. He followed that three-strikeout game by reaching base four times with two doubles off the wall.
The Holliday family is entrenched in Stillwater, an isolated college town still 20 minutes away after exiting Interstate 35. Matt and his older brother, Josh, effectively grew up at Allie P. Reynolds Stadium, OSU’s former ballpark. Their father, Tom Holliday, was among college baseball’s best regarded pitching coaches, eventually getting the chance to lead the Cowboys after program legend Gary Ward retired. A decade after Tom’s tenure ended, Josh took over.
Jackson said his uncle was one of the first to congratulate him on draft night.
That Jackson will always be tied to Stillwater means something to the Hollidays. After Matt’s playing career ended in the fall of 2018, he and Leslee moved back from Florida to be closer to their families. Jackson, months into his freshman year, had uncertainties, feeling a lot of change was happening at once.
He often sought a fully thought-out process before any decision. Whenever he got in trouble with Leslee as a child, he would calmly say, “Well, maybe we should talk about this,” sometimes prompting her to reconsider, if only temporarily.
The move, though, allowed father and son to be around the game together in a new way, with much of Matt’s first spring in retirement spent serving as Harris’ hitting coach for Jackson’s freshman season at Stillwater.
Matt joined his brother at OSU the next year, having bypassed the chance to play for his dad there after the Colorado Rockies drafted him out of Stillwater High. Jackson’s decision is, in that way, a repeat. It was one he made on his own.
“Matt and Jackson and that family could have went anywhere they wanted to go, and he probably still would have been the No. 1 pick,” Harris said. “But we’re lucky it was Stillwater.
“There’s no one more proud of what happened to him than our team because we know what kind of guy he is. He’s genuine. There’s nothing not real about him.”
Matt is well aware of the pressures and sacrifices that face professional athletes, and he’s worked to make sure his sons, with dreams of following his path, are too. He’s about to learn how effective those teachings were.
“You sort of have this underlying, not anxiousness, but just that parental instinct to protect your kids,” Matt said. “You never know for sure if you’ve done it as best you possibly can, but I feel good about him taking on this challenge.”
Jackson believes his childhood around the game has him “about as prepared as you can be to take on this lifestyle.” Leslee said if there does turn out to be something he struggles with, he won’t be afraid to ask for help.
“He’s just very steady,” she said. “Honestly, I am so excited to see what the Lord does in his life. He has a unique gift, and he has a crazy passion, and he loves to compete. He loves to be a part of a team. I think it’s just time. It’s time for him to go and see how everything shakes out for him.”
Minutes after Jackson was drafted and the initial media wave cleared, Matt and Leslee sat down with him in a sibling’s room and stressed the importance of celebrating what he had achieved before the journey to Baltimore began, to not let the joy of the moment pass him by.
It didn’t. He showed it his own way.