'I'm very lucky': Jackson Holliday has huge fan in dad Matt

This story was excerpted from Jake Rill’s Orioles Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

BALTIMORE -- It was easier for Matt Holliday to attend his oldest son Jackson’s baseball games earlier this decade, when Jackson was playing at Stillwater (Okla.) High School. Now, Jackson Holliday is a big leaguer, traveling around the country and playing in the same ballparks Matt did during his own 15-year MLB playing career from 2004-18.

But Matt still finds the time to be there plenty for Jackson. Last month, the Holliday family was a constant presence in the stands at Camden Yards for Orioles home games.

“I’m very blessed to be able to have a great family and a dad that really loves his kids. For him to be able to be here means a lot to me,” said Jackson, reflecting ahead of Father’s Day on Sunday. “Obviously, I’ve got a big family, and for him to make it a priority to want to come out and support me and my family, it’s pretty cool. To be able to lean on him and my mom [Leslee] both, I’m very lucky.”

The younger Holliday had a challenging rookie season in 2024, when he arrived in the big leagues for the first time on April 10 in Boston, where his dad and family sat in the Fenway Park stands. The 2022 No. 1 overall Draft pick was later sent back down to Triple-A Norfolk before returning on July 31 and finishing the year with a .189 average and a .565 OPS in 60 games for Baltimore.

This year, Holliday has solidified himself as the O’s everyday second baseman and is even building a solid All-Star case. The 21-year-old entered Friday hitting .265 with 10 doubles, two triples, eight home runs, 27 RBIs and a .746 OPS through 61 games.

Matt Holliday has been impressed, but not only by Jackson’s improved play on the field.

“I’m most proud of who he is as a human and how he handles himself and how mature he is. It’s great,” said Matt, who was a seven-time All-Star. “He’s so emotionally stable and handles failure and handles how hard the game is really well. I didn’t have any question of whether he would handle it the right way, and he’s very competitive. He expects a lot out of himself.

“I’m not surprised. He’s a very, ‘Figure out what the problem is, let’s fix it,’ kind of person. That’s who he is. I’m proud of the way he’s playing, and I’m mostly proud of who he is as a person."

Unsurprisingly, Matt and Jackson still find a lot of time to talk throughout the course of the baseball season. Sometimes, those conversations are about ball -- such as small things Matt is noticing about Jackson’s swing mechanics -- but more often, they’re about life.

Jackson’s maturity is nothing new. Matt once joked about his oldest child being like a “third parent” for his younger siblings -- brothers Ethan and Reed and sister Gracyn.

When it comes to the baseball aspect, Matt has noticed one way in which Jackson is even better than he was early in his MLB career.

“He knows himself really well and is just making adjustments and looking at things at such a young age,” Matt said, “something that I wasn’t nearly as good at, or as mature, as the kind of adjustments and things that he is seeing and feeling and working on at such a young age.”

In 2022, Matt helped Jackson go through the MLB Draft process. The family didn’t have to wait long on July 17 of that year, as Jackson was the first player to come off the board, with the Orioles selecting the toolsy infielder from the prep ranks.

Ethan Holliday, now 18 himself, could soon have a similar experience. The Stillwater High School standout is eligible to be taken in the 2025 MLB Draft -- set for July 13 and 14 in Atlanta -- and could go No. 1 overall as well, as he is projected to go first to the Nationals in the latest mock from MLB Pipeline’s Jim Callis.

As Jackson knows, Ethan has somebody valuable to fall back on at home (and, eventually, in the big league stands) in Matt.

“As far as being a good dad and a good person, it’s very easy to look up to him, for sure,” Jackson said. “He’s a great resource to what we’re going through, and we’re very lucky to have him.”