BOSTON — The day Jackson Holliday signed with the Baltimore Orioles, the 2022 No. 1 pick sat between general manager Mike Elias and super-agent Scott Boras at Camden Yards and said he hoped to be in the majors in “two years or less.” It was the sort of preposterous prediction an 18-year-old might make after signing for $8.19 million. But it’s not how the road to the show goes for high schoolers.
Two years or less.
It was audacious. It was also accurate.
Holliday, now 20, sat in the visiting dugout Wednesday at Fenway Park ahead of his debut, with reporters encircling him and autograph seekers occasionally calling out his name. When “Jackson” didn’t get his attention, they’d try “Mr. Holliday.” This did not work, in part because two other Mr. Hollidays were within earshot — Jackson’s grandfather Tom, a longtime college coach, and Jackson’s dad, Matt, a 15-year major leaguer. Jackson remembered signing his name inside the Green Monster as a kid.
“I know my dad lost a few World Series (games) here,” he said, to the amusement of the assembled Boston media.
Holliday reached the majors 20 months and 20 days after signing.
“If you give yourself goals,” he said, “you’ll reach them every now and again.”
Holliday started at second base and batted ninth against the Red Sox. He went 0-for-4 while driving in a run with a groundout. He turned a smooth double play in the second inning but later missed a basket catch with his back to the infield. It was, all in all, not the debut of his dreams. But it ended with a 7-5 road win and celebratory high-fives as the Orioles left the field.
“It’s all I could have asked for,” he said. “Playing in the big leagues. A stadium full of fans. Two really good teams. I can’t ask for more — except for maybe like four hits.”
Jackson grew up in major-league clubhouses, but for the first time, this one was his. His stall in the clubhouse was between Adley Rutschman and Gunnar Henderson, and in the same row as Colton Cowser and Jordan Westburg, whose three-run homer was the difference in Wednesday’s game.
“There’s not a more excited stretch of guys in the clubhouse right now — to have each other on the same club again,” Westburg said. “We’re all smiles.”
Jackson’s debut came almost 20 years to the day after his father’s. That was April 16, 2004. Jackson was 4 months old.
“He’s wanted to do this for as long as I can remember,” Matt said Wednesday as he watched his son’s first big-league batting practice. Matt said it felt even more fulfilling watching one of his kids achieve a dream than when he’d lived his own.
Jackson is, for the first time in his pro career, wearing No. 7, which is meaningful on two levels. It’s the number his dad wore for most of the back half of his major-league career. And it’s a number the Orioles had unofficially retired, as it was last worn in 1992 by manager Cal Ripken Sr. — and previously by his son Billy. Cal Ripken Jr., the Hall of Famer who’s part of the Orioles’ new ownership group, said the Ripken family gave its blessing.
Jackson is accustomed to high expectations. He seems unshaken by them.
“It’s different. It’s a lot,” Jackson said. “But I feel like I was born to handle that.”
There’s no shortage of stories to back up that thought. Everyone has one, even Tony Kemp, the guy whose roster spot Jackson took.
Shortly after Triple-A Norfolk’s game ended Tuesday night, Tides manager Buck Britton set up an iPad in his office and let the camera roll as he let Holliday in on a secret he’d been keeping all evening.
Britton broke the news, and Holliday broke into a smile.
“Call your dad,” Britton said.
“I will,” Holliday replied.
Holliday stepped outside the Norfolk clubhouse, phoned his dad and told him to find his way to Boston. Matt was at his son Ethan’s high school game. He started looking up flights on his phone.
“It was not easy getting from Stillwater, Okla., to Boston on short notice,” Matt said. Finally, he called in a favor with a friend who has a private plane. “Sometimes you have to spin that token,” Matt said, with a laugh, “so I did.”
The plane was available, but it was scheduled to fly out of Stillwater at 4:45 a.m. The Hollidays made that work.
Meanwhile, Jackson and his wife, Chloe, packed their Norfolk apartment, dropped off their puppy, Coconut, with teammate Kyle Stowers, then drove to a hotel in Richmond, Va. After three hours of sleep, they headed to the airport for a 6 a.m. flight to Boston. A few hours before his debut, Jackson said he still hadn’t had a sip of caffeine all day. He had more than enough adrenaline.
“It’s been quite the day,” he said, “but I wouldn’t change it for anything.”
Neither would Paul Siani, a 10-year-old from Sykesville, Md. He’d driven up to Boston with his dad, Steve, for the Orioles-Red Sox series. On Tuesday, Paul scooped up three batting practice balls, cheered on an O’s victory, then fell fast asleep in their hotel room. His dad told him the good news when he woke up.
“I was like, ‘No frickin’ way!’” Paul said.
Father and son toured Fenway Park before Wednesday’s game, dressed head to toe in orange. They had tickets in the right-field corner, and Paul was hoping Jackson would pull one their way. But, in a moment away from Paul, his dad spilled a secret.
He’d upgraded to new seats.
They’d be sitting behind the Orioles dugout, a few rows from the Hollidays.
“It’s going to be sick,” Steve said, gleefully. “He has no clue.”
Conor Dines, from Framingham, Mass., was one of the first fans to get an autograph from Jackson Holliday, big leaguer. Dines, who played college ball in New Hampshire, always has a baseball in his car, in case a buddy ever wants to play catch. He thought to pocket the ball before taking a train to Fenway on Wednesday afternoon.
“I was like, we’ll see what happens,” he said.
Jackson emerged before batting practice and signed the ball.
“He’s one of the most touted prospects in recent years,” Dines said. “I wanted to be part of history.”
Jackson appears to be the final piece to the lineup the Orioles envisioned years ago when Elias and manager Brandon Hyde arrived and began building belief in an organization adrift. Though, when that idea of Jackson as a missing piece was presented to Hyde on Wednesday, the manager smirked and said, “I mean, we won 101 games last year, so I thought we put together a pretty good lineup.”
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