Hollidays soak in 'surreal' debut for top prospect Jackson

Matt Holliday reflects on son's rapid ascent to MLB: 'It’s what he’s always wanted to do'

April 11th, 2024

BOSTON -- It’s not easy to get from Stillwater, Okla., to Boston on short notice. and his family learned that Tuesday night. But there was never a chance the 44-year-old was going to miss the MLB debut of his firstborn son, Jackson, roughly 22 hours from then.

So after scouring through the potential flight options on every airline, Holliday called in a favor. He needed to borrow a ride on his friend’s private plane.

His friend came through.

“Sometimes, you have to spend that token, and so I did,” Holliday said. “I’m probably forever in debt to him, but that’s fine.”

The Hollidays, who were airborn by 4:45 a.m. CT on Wednesday, made it to Fenway Park well before the 7:10 p.m. ET first pitch for an Orioles-Red Sox clash that marked the first big league game for , MLB Pipeline’s No. 1 overall prospect. His family members took in Baltimore’s 7-5 win from front-row seats directly next to the O’s third-base dugout.

The youngster said his family got hooked up with those seats by former Orioles and Red Sox first baseman Kevin Millar, who was also in attendance.

“To be able to look over there and have [my dad] and my brother and my grandpa sitting down the line, it was really cool to be able to see them,” Jackson Holliday said. “It’s quite an experience.”

For Matt -- a seven-time All-Star who had a 15-year MLB career as an outfielder -- it was special to see his oldest child continue the family’s Major League legacy.

“It’s exciting. I’m really happy for him,” the elder Holliday said. “It’s what he’s always wanted to do, and it’s kind of surreal that he gets to come out here and play on this field. He’s been on this field.”

Jackson spent his childhood on a lot of big league fields. He followed Matt from one city to the next, running around as a toddler and later fielding ground balls alongside MLB players.

It was always clear to the Hollidays that that’s where Jackson belonged.

“To think about that little fart running around like he owned the field when he was 2 years old, and now, he’s going to do it,” said an emotional Tom Holliday, Jackson’s grandfather. “It’s like, ‘Wow.’ That’s the only word I can think of. I knew it was going to happen; I didn’t know when. There’s no way to prepare.”

Go down the line of Jackson’s family members in attendance at Fenway Park on Wednesday night, and all of them would have said the same thing -- they’re not surprised he made it here. One of them was Tom, a former baseball coach who had a five-decade run in the college ranks that included a stint as the head coach at Oklahoma State (1997-2003).

Others in attendance included Holliday’s mom (Leslee), his brothers (Ethan and Reed), his sister (Gracyn) and his wife (Chloe).

Shortly after meeting with the media for the first time as a big league player, Jackson took the field for batting practice. While he took his cuts, Matt and Ethan -- a top high school prospect in the Class of 2025 -- stood behind the cage. At times, they all three chatted and enjoyed being on a big league field together again.

“It’s everything we’ve ever dreamed of. And I’m super proud of him,” Ethan said. “I know how hard he’s worked.”

As skilled as the young Hollidays are at baseball, they may not have made it this far without Matt. He’s been an invaluable lifelong resource who is helping to get his kids to the same level that he first reached in 2004, only four months after Jackson’s birth.

Now, Matt is enjoying watching his kids play -- Jackson in the Majors and Ethan, a current Stillwater High School standout, not that far behind. It’s why the elder Holliday isn’t coaching or working in baseball. He wants to be there for moments like Wednesday.

“To have a dad that has put everything aside until his kids take their course, they’re pretty lucky kids,” Tom Holliday said.

Meanwhile, Matt was feeling quite fortunate himself upon his return to Fenway Park. He played 12 regular-season games at the historic ballpark, as well as five World Series contests -- two with the Rockies in 2007, then three for the Cardinals in ‘13.

None will be as memorable for him as Jackson’s debut.

“He’s wanted to do this as long as I can remember. It’s always more fulfilling to watch your kids achieve things than yourself,” Matt Holliday said. “He just plays with a lot of joy because he loves to play, and I enjoy watching that.”