What makes Orioles' Jackson Holliday ready for MLB debut? Family, ex-teammates talk top prospect

STILLWATER, Okla. — Jackson Holliday briefly placed his left hand on his black-and-orange batting helmet as he jogged toward first base.

It was a subtle mannerism, a quirk that wouldn’t jump out to an ordinary fan watching Holliday demolish a four-seam fastball for a grand slam during spring training with the Baltimore Orioles.

Jimmy Harris automatically noticed.

Harris, Holliday’s former Stillwater High School baseball coach, had seen that little eccentricity more times than he could count. Whenever Holliday hit the ball, he ran partway down the first baseline and tapped his helmet.

“Go watch his high school clips, and go watch some of his pro clips,” said Harris, who now coaches at Dale. “It’s funny because he’s doing almost the same thing. It’s great.”

It started as a necessity. Matt Holliday said his son used to have a helmet that didn’t fit, so Jackson made sure it wouldn’t fly off. He probably won’t have to worry about ill-fitting headgear in The Show, but Matt said habits stick.

A few weeks before Jackson’s major-league debut, his father took batting practice with Stillwater’s team on a cloudy Wednesday, towering as a quiet Hercules among lively amateurs. The Hollidays are forever linked to this humble but manicured field tucked into Couch Park. Here, only two years ago, Jackson sharpened the skills that have propelled him through the minor leagues and onto the biggest stage.

Jackson's time has arrived. ESPN first reported Tuesday night the Baltimore Orioles are calling up Holliday, the No. 1 overall pick in 2022 who is just 20 years old and regarded as the best prospect in baseball.

Friends and loved ones say he’s the guy they have always known. Endearingly familiar tendencies – from his focused facial expression to his helmet check when he records a hit – show up in his pro highlights. He continues to fish and golf. He married Chloe, his high school sweetheart, in January, and they visit home during his time off.

While Stillwater influences Holliday, Major League Baseball’s new bright star left a lasting impression on the town that helped raise him. His calm confidence imprinted on the Pioneers, particularly the program’s younger Hollidays. Ethan Holliday, Jackson’s younger brother, is a rising MLB prospect as a junior. Brady Holliday, the son of Oklahoma State coach Josh Holliday, is a promising freshman who grew up playing whiffle ball with his soon-to-be-big-league cousin.

“Man, it’s just crazy because I know him,” said Brady, a second baseman. “We’re family, and he’s out there doing all that. It’s cool. It makes me want to do it, too.”

Jackson Holliday ‘just jumps right in’

Ethan said Jackson has “torn up” every level of pro baseball with “undeniable” numbers. After the Orioles selected Jackson in the 2022 MLB Draft, he posted a .396 batting average at Low-A Delmarva, recording 16 RBIs, six doubles, a triple and two home runs. This year, with Triple-A Norfolk, he batted .333 with nine RBIs, five doubles and two home runs.

Although Jackson impressed at spring training with a grand slam against the Toronto Blue Jays, the Orioles reassigned him to minor league camp, surprising baseball devotees who figured he would make the Opening Day roster.

“It’s a business,” Ethan said in late March. “When that time comes, it comes.”

Matt has taught his sons about patience. The seven-time All-Star spent five years in the minor leagues before the Colorado Rockies called him up in 2004, but Jackson didn’t have to wait nearly as long. The baby-faced old soul is learning to compete among vets who have watched him grow up.

This year, Jackson walked into spring training to find seasoned infielder Kolten Wong playing for Baltimore.

Wong knew Jackson as the son of Matt, his former St. Louis teammate.

For Matt, these reunions are fun, albeit surreal, to see.

“It is a little strange to see him around some older guys,” Matt said, “but he’s grown up around it. He just jumps right in and lets his play do the talking.”

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Steady and stable

Jackson’s even-keeled nature pilots him through pressure-packed situations.

His reaction to an at-bat rarely indicates if he struck out or drove in a run. No matter the outcome, Jackson simply plays baseball.

“I think that’s one of the hardest things to do,” said Stillwater senior Parker Jeffery, “is be able to not think about the past or what you’ve done if you messed up, and being able to shake it off.

“He knew he was pretty good, and he never told anybody that.”

Jackson’s steadiness is an unexplainable mystery. In Stillwater, it amazed Harris, who asked Matt how a teenage Jackson managed to keep his composure with MLB scouts swarming his high school games.

Matt said he didn’t know.

“He loves to compete,” Harris remembered Matt saying. “He loves challenges.”

Jackson showed that passion during a moment that lives in Stillwater baseball lore. During his senior season, he stepped up to bat in a regional game with Stillwater and Owasso tied at 1. The Owasso dugout was talking trash, Ethan remembered.

Jackson obliterated the baseball and gazed at it, silencing the Rams with his homer.

Then he greeted the Pioneers with uncharacteristic animation. He offered high fives. According to legend, a “Let’s go” cheer even escaped his mouth.

“It was probably the most emotion I’ve seen him show,” Ethan said. “And then the next inning he was levelheaded, just straight-faced.”

More recently, Ethan watched a video of Jackson hitting a home run with the Norfolk Tides. The celebration wasn’t loud, but it was detectable.

“There was a clip of him pumping his fist or something,” Ethan said. “It was kind of funny.”

Ethan knows his older brother, so any break from Jackson's typically businesslike behavior makes the younger sibling chuckle.

As Jackson ascends through the pro ranks, he’s likely to experience more moments that bring out those rarely seen emotions. This is his lifelong dream, the pursuit that began when he imitated major league batting stances as a toddler.

No moment is too big for Jackson because he isn’t allowing it to be. Sure, he’s expanding his game, but he’s still the easygoing, shaggy-haired kid who sported a Ted Lasso “Be a Goldfish” T-shirt in Stillwater’s clubhouse, referencing the popular TV show’s message of having a short memory and moving on from mistakes.

When Jackson began his minor league career, he even carried his Stillwater walk-up song to Delmarva.

It was “Mr. Blue Sky,” the quirky 1970s hit from British band Electric Light Orchestra. The five-minute earworm maintains its mellow pep until adding some surprising drama with cinematic orchestra strings and choral vocals at the end.

Hey there, Mr. Blue.

We’re so pleased to be with you. 

Look around, see what you do. 

Everybody smiles at you.

In Stillwater, the guys wearing Pioneer blue eagerly consume his highlights. In Dale, Harris’ players follow Jackson’s progress, celebrating his home runs.

When Harris watches a new clip of Jackson playing pro ball, no matter how amazing the feat, the coach isn’t surprised.

Chances are, he saw it happen in Couch Park first.

This article originally appeared on Oklahoman: Jackson Holliday: What makes MLB's top prospect so prepared for debut