As the first half of the MLB season came to a close Sunday, executive vice president and general manager Mike Elias can look around the Orioles organization and feel confident in its direction. Baltimore is heading into the All-Star break at .500, and with the first overall pick in Sunday night’s draft, the Orioles buoyed an already prospect-rich farm system with the selection of high school shortstop Jackson Holliday.
“I think this Orioles organization is in the healthiest spot it’s been in in a very long time,” Elias said. “And it just got a lot healthier 20 minutes ago.”
Jackson, who the Orioles selected out of Stillwater High School in Oklahoma, was named Baseball America’s high school Player of the Year. The 18-year-old is the son of seven-time All-Star outfielder Matt Holliday, so he’s already been around a big league clubhouse.
There’s still plenty to refine about his game — as is the case for any high schooler — but the pick was as close to a consensus as Elias could wish for among the Orioles’ draft room. Once a contract is signed between Baltimore and Holliday, the rookie will report to the Florida Complex League to begin his professional career.
Until then, here are five things to know about the Orioles’ first overall selection.
Holliday isn’t alone in this. For the first time ever, the top two picks in the draft were sons of former major league players — Holliday to the Orioles and Druw Jones, the son of Andruw Jones, to the Arizona Diamondbacks.
Matt Holliday played 15 years in the majors, including eight with the St. Louis Cardinals, whom he represented four times in the Midsummer Classic.
But beyond the potential power and speed between Matt and Jackson Holliday, the similarities largely end there. For one, they play different positions. Jackson is a left-handed batter while his father hit right-handed.
“He’s his own player,” Elias said.
Holliday spent plenty of time in major league clubhouses, though, with his dad retiring once he turned 14. Being up close to that lifestyle helped prepare Holliday for this moment.
“I remember being in the clubhouse ever since he got to St. Louis,” Jackson Holliday said. “It’s definitely an advantage. I’ve gotten to see what it takes to get to the big leagues, and how players — even when they’re at the top of their game — how they still work to maintain it.”
It’s hard to figure exactly how players will all fit into an organization, and the Orioles have plenty of middle infield talent already in the upper levels of the minors, including Jordan Westburg and Gunnar Henderson, who rank as their No. 4 and 2 prospects, according to Baseball America. But Elias expects Holliday to remain a shortstop as a pro.
And with the athleticism of most shortstops and their ability to move around the field, finding playing time shouldn’t be difficult. Elias noted how when he was with the Houston Astros, they selected Alex Bregman the year Carlos Correa debuted, and “we never worried about it, and sure enough found a way to get both of those great players into the lineup.”
Holliday knows there will always be competition for the shortstop role. But he’s eager to hold down the position.
“The shortstop is kind of where the best player likes to play,” Holliday said. “Every team that I’ve gotten to be a part of has had a lot of great players, and I’ve gotten really good at playing other positions. I played a lot of second base last summer. But shortstop is kind of my lane and what I enjoy doing.”
Beyond having a dad who played in the majors, Holliday’s family is full of coaches. His uncle, Josh, is the coach at Oklahoma State, and his dad is an assistant there. Holliday’s grandfather and great-uncle previously coached at Oklahoma State, too.
That’s the school Holliday had been committed to, but after being selected with the first pick, he likely will never play for the Cowboys. But his uncle, Josh, wasn’t too hurt to learn he’ll be losing his top recruit.
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“He was very excited tonight,” Holliday said of his uncle. “It was kind of cool to see. He was one of the first people that I saw after, so I think he’ll be fine.”
Elias admitted Holliday wasn’t initially in the Orioles’ plans to be the top selection during last year’s winter meetings. But a rapid development leading into Holliday’s senior season this spring sent scouts flooding into Oklahoma to see him play, and they were wowed.
Holliday slashed .685/.749/1.392 with 52 extra-base hits and 79 RBIs. His 89 hits broke a national single-season high school record that belonged to current Philadelphia Phillies catcher J.T. Realmuto.
Holliday said he was able to complete online classes, allowing him and his dad to “take advantage of everything I could to hopefully be in this position.”
“Me and my dad were able to train and work out and hit almost every single day, and it kind of grew me as a whole player,” Holliday said. “I’m someone who wants to be good at 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, and it worked.”
Whenever Holliday reaches the majors and plays at Camden Yards, it won’t be his first time playing baseball inside Oriole Park. When his dad played for the New York Yankees in 2017, Holliday shagged fly balls during batting practice at Camden Yards.
“It’s something that I still remember and I’m very excited to get back to that point,” Holliday said. “They’re a great organization and they’re heading in the right direction, and I’m excited to be a part of it.”