With father in front row, Orioles’ Jackson Holliday turns new page in family legacy

BOSTON — Six years after Matt Holliday stepped off a major league field for the final time as a player, his family name is once again back on a lineup card.

Jackson Holliday made his highly anticipated MLB debut for the Orioles in their 7-5 comeback win over the Boston Red Sox on Wednesday night. After a hectic 24 hours in which Jackson got three hours of sleep, Matt called in a favor to get a couple of seats on a private plane and the entire Holliday family converged on Fenway Park, Jackson added a new entry to the family legacy as a second-generation major leaguer.

“It’s all I could have imagined,” Holliday said after going 0-for-4 with an RBI groundout. “Playing in the big leagues, a stadium full of fans and two really good teams, I can’t ask for more except for maybe like four hits, but that’s a lot to ask for. But it was an awesome experience.”

Matt secured a few tickets near the Orioles’ on-deck circle from longtime friend Kevin Millar, a member of Boston’s 2004 World Series roster, and sat with Jackson’s younger brother Ethan and their grandfather. Three generations of his family watched as Jackson, the 2022 No. 1 overall draft pick and consensus top prospect in baseball, lived out his childhood dream.

“It’s exciting,” Matt said on the field before the game. “I’m really happy for him. 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. I think he’s already signed the [Green Monster] wall when he was a kid. So, yeah, I’m just really happy for him. I’m excited that he’s met his goal of getting here and now, the goal was to play well and be a good player on a winning team.”

During his career, Matt was one of the best corner outfielders in the league. From 2004 to 2018, he ranked sixth among all hitters in RBIs (1,220), seventh in doubles (468), eighth in hits (2,096) and 17th in home runs (316). He made seven All-Star teams, won four Silver Slugger Awards, earned Most Valuable Player votes in eight separate seasons (including two runner-up finishes) and played a pivotal role in the St. Louis Cardinals’ 2011 World Series run.

Jackson has the potential to add to that legacy and perhaps even improve on it. Matt was a seventh-round pick who didn’t reach the majors until he was 24. Jackson, who has the benefit of learning to hit at an early age from a dad who is an accomplished hitting coach in addition to being a former player, was already one of baseball’s most exciting young players before he got the call-up to the majors.

“We’re excited to watch him play,” Orioles manager Brandon Hyde said. “It’s a big deal, and to have a No. 1 prospect in baseball on the club and make his debut at Fenway Park, that’s a special place. … So we’re excited for him.”

Fenway Park was the stadium where Matt endured heart-wrenching defeats to the Red Sox in two World Series — one with the Colorado Rockies in 2007, and another with the Cardinals in 2013. Now, the stadium carries new meaning for him; it’s the place where he watched his oldest son suit up as an MLB player for the first time.

“I was telling [teammate Colton] Cowser, he was saying that he’s going to sign his name in the [Green] Monster,” Jackson said. “I believe me and my brother did that whenever we were here a long time ago. I know my dad lost a few World Series here but other than that, I’ve got good memories.”

Baltimore, where Holliday will make his home debut Friday, has a strong chance of becoming as special to the Oklahoma-based family as Denver or St. Louis.

The Orioles have plenty of experience with second-generation stars. Cal Ripken Jr. spent the entirety of his Hall of Fame career in Baltimore, including three seasons with his father, Cal Ripken Sr., as his manager. Holliday chose No. 7, the same number the late Ripken Sr. wore, for his uniform after Matt reached out to Ripken Jr. for their blessing.

“It’s really cool for me to be able to wear that and to be able to share that with their family and it’s good to represent them and wear that number. It’s really special,” Jackson said.

Ripken is a name synonymous with baseball royalty. Matt did well to etch the Holliday name in a few entries of the MLB record books, but it’s now up to Jackson, and perhaps his younger brother Ethan — who is already starting to gain attention as a draft-eligible prospect in 2025 — to cement the family’s place in baseball lore.

“It’s always different with your kids and you get a chance to watch your kids pursue their passion, and he’s wanted to do this since he was — as long as I can remember,” Matt said. “It’s always more fulfilling to watch your kids achieve things than yourself so, like I said, I’m super excited for him and excited to watch him go out here and play.

“He just plays with a lot of joy because he loves to play, and I enjoy watching.”