‘He is comfortable here’: How Jackson Holliday’s clubhouse past helps his MLB future
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Tim Kurkjian, ESPN Senior Writer
It was 2:30 pm Friday, nearly five hours before second baseman Jackson Holliday‘s first game at Oriole Park at Camden Yards. He was the only player on the field, and working on only a few hours of sleep after a late night flight from Boston, but he was full of life as he posed for a baseball card shoot with Topps. Out of the Milwaukee Brewers dugout came another phenom, outfielder Jackson Chourio. The Jacksons embraced, then posed for pictures.
A writer approached Holliday and said, “Got your hands full?”
He smiled and said, “Yes, always.”
Those hands have been full most of his life, but they are big hands, sturdy hands — hands capable of juggling much more than a 20-year-old has a right to.
“He looks like he’s 12, he acts like he’s 30, and he has handled it all beautifully,” said Baltimore Orioles catcher James McCann. “He came to (big league) spring training for the first time, and it seemed like it was his 14th. I went to college (at Arkansas), I played in the SEC, we played before 10,000 people every game. . .he came from Stillwater, Okla. Two years ago, he was playing in front of … parents. And then his first game is at Fenway Park.
“Amazing.”
Holliday smiled. “That was an incredible place to start a career,” he said. “It was awesome.”
Holliday was called up on April 10, just 10 games into his year at the Triple-A Norfolk Tides, and played two games at Fenway Park. He went hitless, and again in his first game at Camden Yards. After an 0-for-13 start that included nine strikeouts, he got his first hit on Sunday, a single that eventually made him the game-winning run in the Orioles’ 6-4 win.
“It’s a lot, but it’s been fun. It’s quite an experience. I don’t think I would ever take it for granted, the experience that I’m having,” Holliday told reporters after the game. “If you go 0-for for three or four games, it’s going to happen in baseball. I’d prefer it not to be at the beginning of my career, but it’s going to happen. I’m glad to hopefully learn from it.”
Even on a young team — the Orioles’ average age ranks sixth in MLB — Holliday is notably green, two years younger than shortstop Gunnar Henderson and four years behind Colton Cowser and starting pitcher Grayson Holliday.
Their oldest player, Orioles closer Craig Kimbrel, is 35.
“When I started my career, he was … born,” Kimbrel said, smiling. “He is comfortable here.”
And Holliday is comfortable, despite his age, because he grew up in a major league clubhouse with his dad, Matt Holliday, a career .299 hitter, and arguably the greatest player named Matt ever to play in the major leagues. Jackson was constantly at his dad’s side, even at pre-school age.
“Show Mr. Kurkjian your Ichiro batting stance,” Matt said to his son 15 years ago.
Five-year-old Jackson did Ichiro perfectly, then the stance of many other major league hitters. So when Jackson was called up, Matt received hundreds of text messages from former teammates — Albert Pujols, Yadier Molina, Aaron Judge among them — from his time with the Rockies, A’s, Cardinals and Yankees. They all sent messages because Jackson is their major league son, too. They all played catch with him.
In February 2008 in Tempe, Az., Brewers manager Pat Murphy, then the baseball coach at Arizona State, rented an adjoining house to Matt and Leslie Holliday for that spring training.
“Every time I looked out in the backyard,” Murphy said, “Jackson was hitting with my son.”
Matt, his wife, Leslie, and their younger son, Ethan, were in Boston for Jackson’s major debut.
“For my debut,” Matt said, “I was scared to death. He was not.”
The Hollidays were in Baltimore for Jackson’s home debut, too. They left the next morning because Ethan, a tremendous high school player in Oklahoma, was missing too many games.
“He’s in high school, he’ll be OK,” Jackson said, smiling.
The pressure is enormous being the son of a major leaguer, being considered the best prospect in the minor leagues and being one of the final pieces in what could be a dynastic next five to 10 years in Baltimore. But Jackson Holliday has an advantage: He is not being asked to save the franchise, as perhaps catcher Adley Rutschman was when he was recalled in May 2022. The Orioles won 101 games last season. They are loaded with talent; much even today remains in the minor leagues.
Holliday won’t be the last piece, but he might be the biggest piece — perhaps even bigger than Rutschman and Henderson — given his background and how he has overpowered the game at every stop. Yet he hit ninth in his first five major league games.
When was the last time he hit ninth?
“I did in spring training,” he said. “Before that, it was a while.”
In Holliday’s second game as a big leaguer, the Orioles hit five No. 1 picks in order in their lineup: third baseman Jordan Westburg, outfielder Colton Cowser, Holliday, Henderson and Rutschman. But only Holliday was given a sacred number in Oriole history — No. 7, last worn by the late Cal Ripken Sr., one of the most important and instrumental figures in Orioles history, the man who personified the Oriole Way.
Matt Holliday, who wore No. 7, called Cal Ripken Jr. for permission to wear his dad’s number.
Ripken, part of the new ownership group with the Orioles, gladly agreed.
“Now wear it with pride,” Ripken Jr. said.
So far, Jackson Holliday has. It has been a wild week, but he has handled most everything with great poise. Outfielder Kyle Stowers is taking care of his dog in Norfolk. Cowser gave him a ride to the ballpark before the first game at Camden Yards.
He is where he is supposed to be. And now he has the first of what will surely be many, many hits.
The 2025 MLB All-Star Home Run Derby is fast approaching — and the field is set.
Braves hometown hero Ronald Acuna Jr. became the first player to commit to the event, which will be held at Truist Park in Atlanta on July 14 (8 p.m. ET on ESPN). He was followed by MLB home run leader Cal Raleigh of the Seattle Mariners, James Wood of the Washington Nationals, Byron Buxton of the Minnesota Twins, Oneil Cruz of the Pittsburgh Pirates, Junior Caminero of the Tampa Bay Rays, Brent Rooker of the Athletics and Jazz Chisholm Jr. of the New York Yankees.
On Friday, however, Acuna was replaced by teammate Matt Olson.
With all the entrants announced, let’s break down their chances at taking home this year’s Derby prize.
Full All-Star Game coverage: How to watch, schedule, rosters, more
2025 home runs: 17 | Longest: 434 feet
Why he could win: Olson is a late replacement for Acuna as the home team’s representative at this year’s Derby. Apart from being the Braves’ first baseman, however, Olson also was born in Atlanta and grew up a Braves fan, giving him some extra motivation. The left-handed slugger led the majors in home runs in 2023 — his 54 round-trippers that season also set a franchise record — and he remains among the best in the game when it comes to exit velo and hard-hit rate.
Why he might not: The home-field advantage can also be a detriment if a player gets too hyped up in the first round. See Julio Rodriguez in Seattle in 2023, when he had a monster first round, with 41 home runs, but then tired out in the second round.
2025 home runs: 36 | Longest: 440 feet
Why he could win: It’s the season of Cal! The Mariners’ catcher is having one of the greatest slugging first halves in MLB history, as he’s been crushing mistakes all season . His easy raw power might be tailor-made for the Derby — he ranks in the 87th percentile in average exit velocity and delivers the ball, on average, at the optimal home run launch angle of 23 degrees. His calm demeanor might also be perfect for the contest as he won’t get too amped up.
Why he might not: He’s a catcher — and one who has carried a heavy workload, playing in all but one game this season. This contest is as much about stamina as anything, and whether Raleigh can carry his power through three rounds would be a concern. No catcher has ever won the Derby, with only Ivan Rodriguez back in 2005 even reaching the finals.
2025 home runs: 24 | Longest: 451 feet
Why he could win: He’s big, he’s strong, he’s young, he’s awesome, he might or might not be able to leap tall buildings in a single bound. This is the perfect opportunity for Wood to show his talent on the national stage, and he wouldn’t be the first young player to star in the Derby. He ranks in the 97th percentile in average exit velocity and 99th percentile in hard-hit rate, so he can still muscle the ball out in BP even if he slightly mishits it. His long arms might be viewed as a detriment, but remember the similarly tall Aaron Judge won in 2017.
Why he might not: His natural swing isn’t a pure uppercut — he has a pretty low average launch angle of just 6.2 degrees — so we’ll see how that plays in a rapid-fire session. In real games, his power is primarily to the opposite field, but in a Home Run Derby you can get more cheapies pulling the ball down the line.
2025 home runs: 20 | Longest: 479 feet
Why he could win: Buxton’s raw power remains as impressive as nearly any hitter in the game. He crushed a 479-foot home run earlier this season and has four others of at least 425 feet. Indeed, his “no doubter” percentage — home runs that would be out of all 30 parks based on distance — is 75%, the highest in the majors among players with more than a dozen home runs. His bat speed ranks in the 89th percentile. In other words, two tools that could translate to a BP lightning show.
Why he might not: Buxton is 31 and the Home Run Derby feels a little more like a younger man’s competition. Teoscar Hernandez did win last year at age 31, but before that, the last winner older than 29 was David Ortiz in 2010, and that was under much different rules than are used now.
2025 home runs: 16 | Longest: 463 feet
Why he could win: If you drew up a short list of players everyone wants to see in the Home Run Derby, Cruz would be near the top. He has the hardest-hit ball of the 2025 season, and the hardest ever tracked by Statcast, a 432-foot missile of a home run with an exit velocity of 122.9 mph. He also crushed a 463-foot home run in Anaheim that soared way beyond the trees in center field. With his elite bat speed — 100th percentile — Cruz has the ability to awe the crowd with a potentially all-time performance.
Why he might not: Like all first-time contestants, can he stay within himself and not get too caught up in the moment? He has a long swing, which will result in some huge blasts, but might not be the most efficient for a contest like this one, where the more swings a hitter can get in before the clock expires, the better.
2025 home runs: 23 | Longest: 425 feet
Why he could win: Although Caminero was one of the most hyped prospects entering 2024, everyone kind of forgot about him heading into this season since he didn’t immediately rip apart the majors as a rookie. In his first full season, however, he has showed off his big-time raw power — giving him a chance to become just the third player to reach 40 home runs in his age-21 season. He has perhaps the quickest bat in the majors, ranking in the 100th percentile in bat speed, and his top exit velocity ranks in the top 15. That could translate to a barrage of home runs.
Why he might not: In game action, Caminero does hit the ball on the ground quite often — in fact, he’s on pace to break Jim Rice’s record for double plays grounded into in a season. If he gets out of rhythm, that could lead to a lot of low line drives during the Derby instead of fly balls that clear the fences.
2025 home runs: 19 | Longest: 440 feet
Why he could win: The Athletics slugger has been one of the top power hitters in the majors for three seasons now and is on his way to a third straight 30-homer season. Rooker has plus bat speed and raw power, but his biggest strength is an optimal average launch angle (19 degrees in 2024, 15 degrees this season) that translates to home runs in game action. That natural swing could be picture perfect for the Home Run Derby. He also wasn’t shy about saying he wanted to participate — and maybe that bodes well for his chances.
Why he might not: Rooker might not have quite the same raw power as some of the other competitors, as he has just one home run longer than 425 feet in 2025. But that’s a little nitpicky, as 11 of his home runs have still gone 400-plus feet. He competed in the college home run derby in Omaha while at Mississippi State in 2016 and finished fourth.
2025 home runs: 17 | Longest: 442 feet
Why he could win: Chisholm might not be the most obvious name to participate, given his career high of 24 home runs, but he has belted 17 already in 2025 in his first 61 games after missing some time with an injury. He ranks among the MLB leaders in a couple of home run-related categories, ranking in the 96th percentile in expected slugging percentage and 98th percentile in barrel rate. His raw power might not match that of the other participants, but he’s a dead-pull hitter who has increased his launch angle this season, which might translate well to the Derby, even if he won’t be the guy hitting the longest home runs.
Why he might not: Most of the guys who have won this have been big, powerful sluggers. Chisholm is listed at 5-foot-11, 184 pounds, and you have to go back to Miguel Tejada in 2004 to find the last player under 6 foot to win.
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