Jackson Holliday has seen it all at the big-league level. He’s been to All-Star games. He’s been to a World Series. He’s been to the playoffs plenty of times. He’s been in and out of clubhouses across the majors.
He did all that as the son of seven-time All-Star Matt Holliday. As he put it to Sporting News, he grew up in the clubhouse.
Now, he’s going to get to try and do all that on his own. Jackson Holliday got the call up to the majors Tuesday, lining him up to make his MLB debut Wednesday against the Red Sox. And being the son of Matt Holliday gives him an advantage over other young rookies, Jackson explained.
“To grow up in a clubhouse and the dynamic of teammates in the locker room I feel like I have a distinct advantage over a lot of people being the youngest guy on the team and still able to have conversations and get to know people on a personal level is something that I feel like I’ve learned from being in the clubhouse and obviously I get to see what it takes to be one of the best big-leaguers in the league also growing up,” Jackson Holliday told SN. “It’s definitely an advantage.”
MORE: Jackson Holliday explains what fans can expect in his rookie season
Jackson Holliday will be the second from his family to reach the majors. He also might not be the last. His younger brother, Ethan Holliday, is widely considered the top prospect in the 2025 MLB Draft. Should he go No. 1 overall, he and Jackson would mark the first brothers to each go at the top of their respective drafts.
As Jackson Holliday prepares to make his MLB debut, get to know the family of baseball’s No. 1 prospect.
Jackson Holliday family tree
Jackson Holliday’s dad: Matt Holliday
Though he might be the No. 1 prospect in baseball, Jackson Holliday has a long way to go until he reaches the accomplishments of his dad.
Matt Holliday was a seventh-round pick by the Rockies in the 1998 MLB Draft out of Stillwater High, the same school as his two oldest sons. There was no certainty he would wind up signing as he was also considered a star quarterback and committed to Oklahoma State, where his dad, Tom Holliday, was the baseball coach.
“Holliday might be an impossible sign unless he gets first-round money, but the loss of Oklahoma State’s offensive coordinator to the Dallas Cowboys has made Holliday look more closely to baseball,” Baseball America wrote. “He has shown little inclination to play college football and professional baseball. Holliday is a five-tool player with excellent power and arm strength.”
But he wound up signing a deal for an $800,000 bonus, per BA, and joined the Colorado organization. Unlike Jackson Holliday, who rocketed through the minors less than two years after graduating from high school, Matt Holliday took until 2004 to reach the big leagues, at which point he was 24. But it was clear upon his arrival he had the potential to be an impact talent.
In 121 games, Holliday posted an .837 OPS with 14 home runs. He finished fifth in National League Rookie of the Year voting.
The slugging outfielder was off to the races from there. He hit .307 with 19 homers the next season, then posted a .326/.387/.586 slash line with 34 home runs in 2006, earning him his first of three straight Silver Sluggers and three straight All-Star nods. He also finished 15th in MVP voting.
The next season, Holliday led the National League in average (.340), RBI (137), doubles (50) and hits (216) to place second in MVP voting. He also helped power the Rockies to their first-ever World Series appearance, where they lost to the Red Sox. Holliday was the NLCS MVP after posting a 1.145 OPS with two homers in four games.
Holliday was traded to the Athletics after the 2008, and he wound up being flipped again to the Cardinals at the trade deadline. He hit .353 in 63 games with St. Louis after the trade, then signed a seven-year, $120 million deal to stay with the Cardinals in the offseason. He posted a .922 OPS in 2010 and earned his fourth All-Star and fourth Silver Slugger, while finishing 12th in MVP voting.
The next year, Holliday and the Cardinals went to the World Series, where they topped the Rangers in seven games. Holliday was a fixture of a dominant stretch of years for the Cardinals as between 2011 and 2015, St. Louis reached the postseason every year, going to the NLCS in all but 2015 and reaching the World Series twice.
Years later, his son will say that Cardinals’ stretch is what he hopes the Orioles can eventually become.
“I hope it’s like the Cardinals,” Jackson Holliday said of his hopes for the Orioles. “Growing up. I got to go to a lot of playoff games and I think that’s kind of what I see personally is kinda how the Cardinals were whenever my dad got there and have unbelievable players and people and … that’s my hope for the Orioles is to be able to play in the playoffs every year and have chances to win World Series. That’s the only thing you can hope for, right, as a player. That’s my goal.”
While with the Cardinals, Holliday was named to four All-Star teams (2010, 2011, 2012 and 2015) and earned MVP votes in four seasons (2010, 2012, 2013 and 2014).
Holliday reached free agency after 2016 and signed a one-year deal with the Yankees, and was part of the team that went to the ALCS. He signed a minor-league deal with the Rockies and appeared in 25 MLB games for them in 2018. He retired after the season.
Holliday finished his MLB career with a .299/.379/.510 slash (.889 OPS) with 2,096 hits, 316 home runs, 1,220 RBI, 1,157 runs scored, 108 stolen bases, 802 walks and 1,362 strikeouts. He is one of 98 players in MLB history with at least 2,000 hits and 300 home runs. Of those players, Holliday is one of only 32 to have more than 800 walks and fewer than 1,400 strikeouts, according to Stathead. Just 11 of those players played in the 2000s.
Following his MLB career, Holliday has largely taken up coaching. He was a volunteer coach at Oklahoma State, where his brother, Josh Holliday, is the head coach, from 2019 to 2022. He was briefly hired to be the Cardinals’ bench coach in November 2022, but wound up stepping down in January 2023 to keep his focus on family.
Though he’s no longer coaching, he still talks with Jackson Holliday about hitting.
“We talk a lot, almost every day just about hitting or how the day went, kinda like he’ll ask questions about the pitcher or stuff like that just simple stuff,” Jackson Holliday told SN. “There’s no secret sauce. It’s just a good dad. Normal conversations and ask how the day went, how my swing feels and usually when I’m hitting as well as I have been lately, there’s not a whole lot of things to talk about when it comes to my swing. Hopefully we can keep it that way.”
Jackson Holliday’s mom: Leslee Holliday
Matt Holliday married Leslee on Dec. 30, 2000, according to The Southern Illinoisan, after having met each other on a blind date in Stillwater, Oklahoma, in 1999. Each had a friend dating one another, and they wanted to set up a double date, pairing Matt and Leslee for an outing.
They had Jackson Holliday, their first son, on Dec. 4, 2003. Matt Holliday would make his MLB debut just over four months later in April 2004. He called Leslee while she was watching the Season 1 finale of “The Bachelorette” to tell her the news. At first, she said she didn’t answer the phone because she wanted to see who the suitor picked, but wound up answering in case it was an emergency.
“Matt keeps calling and calling,” Leslee Holliday told The Southern Illinoisan. “I’m like, ‘What is going on? You know my show’s on?’” she said. “And he says, ‘I’ve only been called up to the big leagues.’”
Leslee Holliday led a Bible studies for the wives of professional athletes in St. Louis, she told The Southern Illinoisan, in an effort to help marriages during the tumult of the seasons. She told the paper she impresses the importance of spouses of athletes maintaining their own identity even as their husbands become more famous in their respective sports.
She continues work as a leading of the women’s ministry for Pro Athletes Outreach in 2024.
Jackson Holliday’s wife: Chloe Cox Holliday
Jackson Holliday got engaged to his girlfriend, Chloe Cox, she announced on Instagram on Dec. 28, 2022. She posted photos of their wedding in January and shared the date as Jan. 6, 2024.
Several of Matt Holliday’s former Cardinal teammates attended the wedding, Jackson Holliday said, something he said showed the camaraderie even years later from those teams.
“I got married this offseason and a lot of those guys that were on those teams were there and just watching the camaraderie and relationships that my dad and those guys have, I think that’s what it takes. In the clubhouse, it’s a tight group. I think you have something special in the works,” Jackson Holliday said.
Jackson Holliday’s middle brother: Ethan Holliday
Baseball fans aren’t likely going to be waiting long to see the next sweet-swinging Holliday reach professional baseball. Ethan Holliday, the second-oldest of Matt and Leslee Holliday’s children, is currently a junior at Stillwater High. And by all accounts, he’s following a similar track to his older brother.
Ethan Holliday is currently ranked as the No. 1 2025 prospect by both Baseball America and Perfect Game. He is currently committed to Oklahoma State, where his uncle is the head coach. However, like Jackson, being selected at or near the top of the draft would likely lead to him going pro.
Though Ethan Holliday is a left-handed infielder, Baseball America compared his physical size (6-4, 195 pounds) more to his dad (6-4, 240 pounds) than his brother (6-foot, 185 pounds). He’s also projecting to be more likely to head to either third base or the outfield rather than stay at shortstop. The site also sees more power in his swing than Jackson’s.
2025 SS @ethanholliday2 (@SHSPioneersBSBL and @OSUBaseball commit) is starting to heat up this spring launching a no doubter deep over the RCF wall to take the early 1-0 lead
#1 player in the ‘25 class showing off his elite power potential@ShooterHunt pic.twitter.com/50HVo1BCCX
— PBR Oklahoma (@PrepBaseballOK) March 25, 2024
Baseball America wrote:
The ease of operation in the batter’s box stands out, with Holliday showcasing a smooth, compact swing from the left side with good rhythm and balance. He tracks pitches extremely well, maintaining a disciplined approach to draw plenty of walks. There is some swing-and-miss to his game, but Holliday has a mature offensive mindset, controlling the strike zone and using the whole field. Holliday drives the ball well now and doesn’t have to sell out to generate that power, with the upside to develop into a 30-plus home run threat. At shortstop, Holliday is a fundamentally sound defender for his age, though at his size, there’s a good chance he outgrows the position and ends up at third base in pro ball, with the middle-of-the-order offensive upside that would project well in a corner outfield spot too.
No brothers have gone first overall in different years of the draft. Ethan Holliday appears to have a chance to make history for the Holliday family.
Jackson Holliday’s youngest brother: Reed Holliday
Jackson’s youngest brother is Reed Holliday, who is the youngest of the four Holliday siblings.
Jackson Holliday’s sister: Gracyn Holliday
Jackson Holliday also has a younger sister, Gracyn Holliday, who is younger than Jackson and Ethan, but older than Reed Holliday.
Jackson Holliday’s uncle: Josh Holliday
Josh Holliday is Matt Holliday’s older brother and the current head coach at Oklahoma State.
Like Matt, Josh Holliday was drafted out of high school, going in the 14th round of the 1995 draft to the Twins. He, however, opted to go to Oklahoma State. He was drafted in the ninth round of the 1999 draft by the Blue Jays and signed with them. He spent two years in professional baseball before shifting to coaching in 2001 at Oklahoma State under his dad, Tom Holliday.
Josh Holliday began as a student assistant coach in 2001 before becoming a full-time coach in 2002. Following the 2004 season, he served as an assistant coach at NC State, then Georgia Tech, Arizona State and Vanderbilt, the latter working under Tim Corbin.
The Cowboys brought Josh Holliday back in 2013 to be the program’s head coach. He became the first former Oklahoma State player to eventually become head coach.
Oklahoma State has been a consistent standout program with Josh Holliday at the helm. The team won at least 40 games in each of his first two seasons and three of his first four years. The Cowboys have been in the NCAA Tournament every season (the 2020 tournament was canceled), and they’ve reached the super regionals in three of those seasons.
In 2016, the Cowboys reached the College World Series and advanced to the semifinals before falling to Arizona in back-to-back games.
The program has four times won the Big 12 Conference and twice finished in the top 10 in national polls. Under Josh Holliday, the Cowboys have had 64 draft picks, including 27 going in the top 10 rounds and eight reaching the majors. He has a career record of 403-219-2 at Oklahoma State.
Jackson Holliday’s grandfather: Tom Holliday
But just as Jackson Holliday isn’t the first in his family to reach the majors, Josh Holliday wasn’t the first to helm the Oklahoma State baseball program. That would be Josh’s and Matt’s dad, Tom Holliday.
Tom Holliday was also an MLB draft pick, having been taken by the Pirates and logging a year in the minors in 1975. However, he returned to his alma mater, Miami (Fla.) as a graduate assistant for the 1976 season. He served in the same role at Arizona State in 1977. The Sun Devils won the national championship his lone year on the staff.
Tom Holliday was hired by Oklahoma State to be the pitching coach under Gary Ward ahead of the 1978 season. He held that role through 1996, when he was promoted to head coach ahead of the 1997 campaign. He continued the strong run of the Cowboys by coaching them to three straight 40-win seasons and no fewer than 34 wins in any campaign during his seven-year run as the head coach.
With Tom Holliday at the helm, Oklahoma State went to the NCAA Tournament four times and the College World Series once, coming in 1999. His contract was not renewed after the 2003 season, and he went to become the pitching coach at Texas for three years, during which time he won his second national championship.
He was then the pitching coach at NC State from 2007 to 2014 before serving in the same role for Auburn in 2015.
In 2017, Cape Cod Baseball League team Chatham Anglers named him the program’s head coach, a role he held from 2018 to 2023. Chatham reached the Cape League Championship in 2018, but fell to Wareham. He stepped down during the middle of the 2023 season due to personal reasons.
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