In 2022, Holliday graduated from Stillwater High School, with a commitment to Oklahoma State.

Jackson is the son of Matt Holliday, who played 15 years in the majors, where he was a seven-time All-Star. Matt had a .299 career batting average to go with 316 home runs and 1,220 RBIs.

Jackson’s uncle, Josh Holliday, has been OSU’s coach since the 2013 season. OSU is 271-153 under Josh.

Jackson’s grandfather, Tom Holliday, coached the Cowboys from 1997-2003, accumulating a 281-150 record.

June 2022: The Orioles chose Jackson in the first round (#1 overall), out of high school in Oklahoma. And Holliday signed for $8.19 million, slightly under the pick value of $8.85 million. He signed with scout Ken Guthrie.

From MLB: This year’s draft marked the second in history that the son of a former major leaguer was selected first overall. The last one was Ken Griffey Jr. in 1987. 

2022 Season: Holliday went No. 1 overall because he had the best combination of hitting ability and tools in the Draft, and the son of seven-time All-Star Matt Holliday lived up to his reputation during his debut. He batted .297/.489/.422 with six extra-bases hits and four steals in 20 games, drew 25 walks versus just 12 strikeouts and reached Single-A.

In 2023, the Baseball America Prospect Handbook rated Jackson as the Orioles' 3rd-best prospect. He was #1 in the winter before 2024 spring training.

Feb 21, 2023: Jackson isn’t your typical 19-year-old. He was raised around baseball as the son of an All-Star outfielder. At 6-foot-1 and 175 pounds, he’s growing to be a talented player in his own right. Mature for his age, he’s already engaged, having popped the question to his girlfriend, Chloe, during a family vacation in Mexico over the winter.

And despite having only 20 games of professional baseball experience, Holliday is participating in his first big league Spring Training . . . even though at this time last year, the shortstop was still in his senior year at Stillwater High School.

After getting selected by the Orioles with the No. 1 overall pick in the 2022 MLB Draft last July, Holliday was included among the club’s list of non-roster invitees for Major League camp this spring, which was announced early this month. Was he surprised?

“I was hoping for one,” said Holliday, the No. 12 overall prospect in baseball per MLB Pipeline. “I wouldn’t have been surprised if I didn’t, but I’m very glad that I did, and I’m looking to make the most of it.” 

It’s uncommon for a player fresh out of high school to have a locker in a clubhouse filled with Major League veterans just seven months after being drafted. Holliday got only a small taste of what the pros are like in 2022, slashing .297/.489/.422 with one homer, five doubles and nine RBIs across eight games in the Florida Complex League and 12 with Single-A Delmarva. That barely even qualifies as a cup of coffee in the baseball world. However, O’s general manager Mike Elias knew it would be the right decision to extend Holliday an invite to big league camp.

“We thought he could handle it; we thought he was ready for it,” Elias said. “He had a really good debut and did well in A ball and seems to be a very mature kid. So we thought it would be a good experience for him, even though that’s not the norm.”

Holliday reported to Sarasota earlier than many of the players in the Orioles’ organization, participating in the team’s development camp from Feb. 6-14. He and four other top prospects in the system worked with Major League staff and instructors before the complex became filled with more proven players.  Since then, the youngsters have stuck around. It’s not an unfamiliar environment for Holliday, considering he went to Spring Training every year when his dad, was playing in the Majors from 2004-18.

So Holliday wasn’t needing a ton of help understanding what this experience would be like.

“He didn’t really have to tell me much . . . just to have fun with it and work hard and get to know these guys, because I’ll be around them for quite a long time,” Holliday said.

Some of the players with whom Holliday has bonded over the past week have included catcher Adley Rutschman (a fellow No. 1 overall Draft pick himself in 2019), infielder Gunnar Henderson (baseball’s No. 1 overall prospect) and outfielder Colton Cowser (the No. 40 overall prospect). That quartet has the potential to be part of the Orioles’ position-player core well into the next decade.

For now, Holliday is just bonding and getting to know them better, since every face coming into the Spring Training clubhouse was a new one to him. They’re facing off in ping-pong and going out for putt-putt and bowling. There’s also friendly competition during workout drills.

Even if Holliday is easily the youngest of the 71 players in Orioles big league camp, he’s blending in well with those who are more experienced.

“I’ve been so impressed watching him,” manager Brandon Hyde said. “It doesn’t look like a kid that just was in high school a year ago. It’s special ability, and he’s really talented.”

Later this spring, Holliday will be reassigned to Minor League camp. But Hyde is planning to insert him into some Grapefruit League action before that time arrives.

That experience should be quite valuable for Holliday, who isn’t likely to reach the Majors until about 2025, with multiple levels still to climb in the Minors. But in addition to learning, he’s enjoying the chances to spend time with his potential future teammates and isn’t taking it for granted.

“It’s been great to be around all the young guys, and to get to be around them every day,” Holliday said. “It’s been pretty sweet.” (J Rill - MLB.com - Feb 21, 2023)

“Jackson, man, for his age, that kid is ridiculous. The things he is doing, his approach at the plate, everything,” Heston Kjerstad, the No. 2 pick in 2020, said.

“And we don’t even know if he is done growing and how big he’ll end up. So, there’s no telling how much power is going to be in that bat or what type of hitter he is going to become as he grows up.” (Connolly - Mar 1, 2023 - TheAthletic.com)

July 1, 2023: At this time last year, Jackson wasn’t yet a professional baseball player. That changed July 17, 2022, when he was selected by the Orioles with the No. 1 overall pick in the 2022 MLB Draft.

As the one-year anniversary of Holliday’s life-changing day approaches, I caught up with the 19-year-old shortstop during a recent visit to Ripken Stadium, where Holliday hit a two-run walk-off home run to lift High-A Aberdeen to a win over Winston-Salem.

MLB.com: You’re nearly one year into your professional baseball career. Has it been everything you expected it to be?

Holliday: It’s honestly more than I could have imagined. It’s been really, really neat to be able to go to big league Spring Training, and then be able to play pretty well this season and be around a lot of great guys that I got drafted with last year and be able to spend so much time with them and play with them. It’s been overwhelmingly good. It’s been pretty awesome.

MLB.com: On April 24, you were promoted from Single-A Delmarva (where you slashed .396/.522/.660 in 14 games this year) to High-A Aberdeen (where you’re slashing .299/.440/.497 through 52 games). What’s been the biggest difference you’ve noticed at the new level?

Holliday: The quality of pitches is definitely different. Guys will be able to throw their curveball in any count. And just the quality of stuff is a little bit better, being able to pitch a little bit differently. It’s more of, I’d say, top-end college guys vs. some top-end high school guys would probably be the way that I can explain it. It’s been a lot of fun. It’s been a good little challenge, and I’m looking forward to the next one. 

 MLB.com: Quite a few top hitting prospects have endured prolonged slumps after they’ve arrived in Aberdeen. How did you avoid it?

Holliday: The first two games, I think I went 0-for-7. So I think I gave the whole thought of, ‘Everyone struggles down here,’ a little bit too much credit. Just going back to my game and looking for fastballs that I can drive and just playing has definitely helped me out, and not thinking about the guys that have struggled, even though they’re great players and most of them are in the big leagues right now.

MLB.com: You said during Spring Training you hoped to reach Double-A Bowie this year. You have to feel that’s attainable now, right?

Holliday: Yeah, absolutely. I think that goal is definitely in reach, and I feel like I’ve done a pretty good job of trying to be able to accomplish it. Just trying to take it day by day, and I trust the organization that they’ll put me in the right spot. That’s still my goal, and I’m looking forward to hopefully the day that I get to go up there and play. MLB.com: You played third base for the first time as a pro at Wilmington. How did that come about, and what was it like playing there?

Holliday: I think it’s just to make sure guys get their innings at second and short. Just being able to have that versatility is definitely important, because the goal is to play in the big leagues, and if they want you to play third or second or short, I’ll be able to do that. I like playing different positions, and it was pretty fun. 

MLB.com: How’s it feel to be MLB Pipeline’s new No. 1 overall prospect?

Holliday: It’s very cool. It’s quite an honor to think about. There are so many great players in the Minor Leagues, and some of them are even in the big leagues. It’s quite an honor to be the No. 1 player. Obviously, Gunnar [Henderson] and Adley [Rutschman] were the No. 1 players the years before, so that’s kind of cool. I like that part of it. Being able to carry on that tradition as the No. 1 prospect being with the Orioles is more important to me than honestly just being the No. 1 player. I enjoy being around those guys, and I look up to those guys, so it’s pretty cool to share that with them.

MLB.com: You’ll be playing in the 2023 SiriusXM All-Star Futures Game on July 8 at Seattle’s T-Mobile Park, along with fellow Orioles prospect Heston Kjerstad. How excited are you?

Holliday: I’m really excited. It’s going to be really cool to be a part of. I’ve been to Seattle once or twice, so I’m looking forward to it. I texted Gunnar Thursday morning, because it was his birthday, and he texted me and told me congratulations and how much fun he had at that last year. So I’m looking forward to it, looking forward to seeing some of the guys that I know and being around Heston a little bit more.

I was excited to see that he’s also going. I think we’re going to live together during Spring Training next year. We’re pretty good buddies, and I’m excited for him. I know he’s had some injury stuff, so it’s really cool to see how much success he’s having and some of the opportunities that he’s getting.

MLB.com: Other than reaching Double-A, any other personal goals for the second half of the season?

Holliday: I would like to steal maybe like 20 more bases and get to 40 stolen bases, that’d be pretty cool. Just trying to improve in every aspect. Obviously, I want to hit some homers and hit doubles and triples. Maybe slug a little bit higher, do some more damage.

MLB.com: Your life is obviously revolving around baseball. What are you doing when you’re not at the ballpark these days?

Holliday: I play MLB The Show, and I watch more baseball. So baseball’s kind of the center of my life. But I go play pickleball every now and then. My dad’s a big pickleball player now, so I’ve been dabbling with that. I just enjoy being around a lot of these guys, and we go golfing on Mondays.

MLB.com: Have your dad and family been up to see you play much?

Holliday: I think he’s came and visited about four times this season. My brother [Ethan] and the rest of my family have been here twice. It’s been good to have them back and forth, but they’re on the summer circuit now with Ethan. I’d like to think that [my dad’s] been very proud of how I’ve been playing, and he calls me and texts me after almost every game.

MLB.com: How much are you enjoying being part of an Orioles organization that’s on the rise, from top to bottom?

Holliday: It’s really cool to be able to play our game and then check the scorebook and see how the Orioles did and see that they won again and Gunnar hit a homer and all these guys that are getting called up are doing great. It’s been really, really cool to be a part of this organization, especially right now. They’re doing so well, and all the guys in Triple-A are doing great and I got to spend a lot of time with them during Spring Training. It’s been pretty awesome. I remember my dad texted me after one day and he’s like, ‘How many of those guys are going to play in the big leagues?’ And I’m like, ‘I think all of them.’ They’re all so talented. It’s an unbelievably talented group of guys. (J Rill - MLB.com - July 1, 2023)

In 2023, Jackson represented the Orioles at the All-Star Futures Game. 

Days after starting in the Futures Game, MLB’s top prospect, Jackson Holliday, made his Double-A debut as a teenager. The 19-year-old had two hits in his first game for the Bowie Baysox. He has raced up three levels already this season and had a .314/.452/.488 line in 57 games with High-A Aberdeen before his latest promotion. (Lockard - Jul 17, 2023 - The Athletic)

In a year full of milestones, Jackson Holliday can cross one more accomplishment off his list: his first Triple-A home run.

MLB's No. 1 prospect went deep for the first time with Norfolk in a 12-10 win over Memphis at Harbor Park. The solo homer was part of an offensive showing in which Holliday reached base four times — a welcome sight nine games into his tenure at this level.

Jackson has progressed from Single-A Delmarva up to the brink of the Majors in his first full professional season. It's been a slow start for Holliday at Norfolk — he was 5-for-33 with seven walks — but he is the only 19-year-old at Triple-A. Notably, the homer wasn't even Holliday's best-struck ball of the game, even with a 98.3 mph exit velocity. In his final time up, after grounding out and walking, he barreled a ball 408 feet off the top of the fence in center for a double — his hardest Triple-A hit at 102.5 mph. (Weinrib - Sep 14, 2023 - milb.com)

2023 Season:  Holliday has burst onto the scene and established himself as the consensus best prospect in baseball at just 19 years old, after being selected with the first overall pick in 2022. Holliday has soared through the Orioles system, traveling through 4 levels of the Orioles system in his first full professional season.

Holliday posted video game numbers this season, slashing .323/.442/.499 across all four levels and he finished the season in Triple-A Norfolk. Holliday can do it all, slugging 12 homeruns, 30 doubles, 9 triples, and stealing 24 bases in 125 games.

Holliday recorded 154 hits in those 125 games and walked 101 times, compared to just 118 strikeouts. The only minor league level that held Holliday below an OPS of .900 was Triple-A, where he still posted a .396 on-base percentage and recorded more hits than games played.

Holliday is the whole package. The only question with Holliday is where he's going to play (since Gunnar Henderson thrived at shortstop in the second half of the season). (Justin Long - Oct. 22, 2023)

2024 Spring Training Q&A:

Question: Are you excited about playing in the Spring Breakout game?

Holliday: “It should be fun. Any time that MLB sets something up like this, it’s pretty neat. I’ve enjoyed playing in the Futures games, and I think it’s something like that earlier in the season. It’s exciting to be able to play with a lot of guys that I’ve spent a lot of time with, especially guys I got drafted with. Obviously, a few of them during big league spring training. It will be fun. I’ll be excited. I’m only playing five innings, but it will be fun.”

Q: It seems as if every national reporter covering baseball has come in here interviewing you. Does that get tiring?

Holliday: “It’s fun. I enjoy doing interviews. I think it’s neat to be able to meet people … I think it’s also very important, as much as playing.”

Q: What’s the biggest thing you’ve learned this spring?

Holliday: “Being able to face really good arms has been beneficial for me … To face guys like Zack Wheeler and all the relievers for the Yankees and just getting exposed to these guys and be able to really attack that at-bat because they’re probably working on something in spring training. It’s been really cool for me to be able to learn that and learn little things with my swing along with a lot of things at second base, a lot of learning so far.”

Q: What was your history of playing second base before this spring?

Holliday: “Depending on whether someone was hurt or the schedule worked out, I would play once a week at second base. It was very raw over there, just playing it like I would play shortstop, trying to get outs, then learning some technical stuff this spring and a little in the offseason, on flips, learning how to turn double plays. It’s a lot more in-depth now. It’s been good to be able to learn that, and I feel a lot better.”

Q: You’ve always been a shortstop and everything’s instinctive. Is second base close to being that instinctive for you yet?

Holliday: “Yeah, I think so. I think when it comes to be able to field a ground ball and throw to first, I think it’s very instinctive. The cuts are a little different. I know as a shortstop you’re mainly the lead guy. That changes just a little bit, but being able to really learn about that and think before it happens, ‘OK, there’s a guy on first base I’m cutting for. I need to know where I’m lined up. There’s no one on base, just being ready before the pitch.’ I think it’s been very helpful for to be able to relax and knowing what to do before it happens. I think that’s been very helpful for me.”

Q: As opposed to last year, you’re starting games and you’re facing elite pitchers, you seem pretty comfortable, don’t you?

Holliday: “I think just getting at-bats and just being able to go up there with confidence. If you go up there, thinking you’re going to get out, you’re probably going to get out, but if you change your mindset and, “OK, I’m going to smash a fastball and just see what happens,’ I think that’s the mindset I’m going with: ‘I’m going to crush your heater,’ just adjust off that. It’s something that I’ve always done. If I go up there timid, and, ‘OK, this guy is an All-Star, he should probably get me out,’ then you’re probably going to get out. I think if you know how to change that mindset, and just go out there and compete and try my best to not let that guy in front of me beat me, it’s been really good, and I’ve felt really comfortable that last few weeks.”  (Rich Dubroff - March 14, 2023)

April 10, 2024: The Jackson Holliday era is about to begin in Baltimore.

The Orioles are calling up the 20-year-old infielder, MLB Pipeline’s No. 1 overall prospect, from Triple-A Norkfolk, a source told MLB.com’s Mark Feinsand. Holliday is expected to be with the team for the second game of their series in Boston.

The No. 1 pick in the 2022 MLB Draft out of high school in Oklahoma, Holliday was slashing .333/.482/.595 with two home runs through 10 Triple-A games in 2024 and owns a career .321 average and .949 OPS in the Minor Leagues. 

A left-handed hitter, Holliday played only 18 games at Triple-A in 2023, when he climbed all four full-season Minor League affiliates. He had a chance to make the O’s big league roster out of Spring Training, but they optioned him two days before the end of camp, with general manager Mike Elias stating the club wanted Holliday to get more reps at second base and additional experience against high-level left-handed pitching. 

“He’s been great,” Norfolk manager Buck Britton recently told MLB.com’s Melanie Martinez-Lopez. “He kind of came down here with a chip on his shoulder. He wanted to prove that what he did at Spring Training wasn’t a fluke and he was ‘the guy.’”

Jackson will be an immediate impact bat for an Orioles team already full of talented young position players. Reigning AL Rookie of the Year Gunnar Henderson was MLB Pipeline’s No. 1 prospect in 2023, and Orioles catcher Adley Rutschman also held the No. 2 spot in 2022 at the time of his debut in May '22. Behind Holliday, there are more reinforcements on the way: Orioles hitting prospects Samuel Basallo, Coby Mayo and Heston Kjerstad are all currently ranked among MLB Pipeline’s top 30 overall prospects.

With Henderson manning shortstop for the O’s, who are coming off a 101-win season and AL East championship, Holliday will likely play second base when he debuts. Orioles second basemen in 2024 are batting .206 with a .632 OPS, so Holliday could provide an offensive upgrade.

Jordan Westburg, who has been playing both second and third, could get more time at third, with Holliday getting a lot of time at second. Veteran utility man Ramón Urías has been slumping early in the season, going 2-for-22 in eight games.

It’s no guarantee the 20-year-old, who will be MLB’s second-youngest active hitter when he debuts, behind Milwaukee's Jackson Chourio, will immediately adjust to Major League pitching. But Holliday has hit everywhere he has gone — including in 2024 Spring Training when he hit .311 with two home runs, two triples and three doubles. And there’s no reason to think Baltimore will be any different. “This guy is just a super-athlete, but he’s great,” Britton recently said. “He interacts with you, he asks questions, and he asks smart questions. His ability to adapt quickly to new things is what’s really impressive and separates him. He’s been a joy both on and off the field.” (T DeRosa & J Rill - MLB.com - April 10, 2024)

MLB debut (April 10, 2024): Holliday didn't have the best of debuts. He went 0-4, striking out twice and grounding out twice, although one groundout resulted in an RBI. Nevertheless, the Orioles' top prospect doesn't just have the physical tools and ability to become a star, he also has an even-keeled demeanor that allows him to move forward to the next at-bat without feeling much of an effect from the poor at-bats he has had previously.

June 16, 2024: Very few fathers and sons have had the opportunity to each play baseball at the highest level. We were reminded of what that looks like when MLB Pipeline’s No. 1 overall prospect, Jackson Holliday, made his Major League debut for the Orioles at Fenway Park back on April 10.

When Holliday, who is currently with Triple-A Norfolk, took the field for the much-anticipated moment, he was wearing No. 7, a number that hadn’t been worn by an Oriole since 1988, when Cal Ripken Sr. and Billy Ripken donned it. But No. 7 was special to the 20-year-old Holliday for another reason, as well -- it was one of the numbers his father, Matt, wore during a 15-year MLB career.

Holliday is the latest son of a former big leaguer to wear his father’s number in the Majors. Here’s a look at the Hollidays and other prominent father-son duos who shared the same uniform number:

Matt Holliday was a seven-time All-Star and four-time Silver Slugger Award winner who played for the Rockies, A’s, Cardinals and Yankees from 2004-18. He won the National League batting title by hitting .340 in 2007, a year in which he also led the league in hits (216), doubles (50), RBIs (137) and total bases (386). He appeared in eight postseasons, winning the ’07 NL Championship Series MVP Award and belting 13 career postseason home runs.  Matt was on hand to witness his son Jackson’s MLB debut, a moment when the pair joined a pretty exclusive club of fathers and sons in the Majors. Despite going only 2-for-34 before being optioned to Triple-A, Jackson is one of the finest-hitting prospects in recent memory, ascending through the Orioles’ farm system quickly -- he went from being drafted first overall in 2022, to the big leagues less than two years later. Holliday needed just 155 games to make the jump, posting a .933 OPS in the Minors before his callup.

Somehow, he never wore the No. 7 during his short stint in the Minors. Not that it was for lack of trying.

“I mean, I tried to wear 7,” he said. “But I just wear whatever number I'm given. Really cool to be able to do that." ( M Randhawa - MLB.com - June 16, 2024)

June 12, 2024: The Prospect with the best power=speed combo for the Orioles: Jackson Holliday, 2B/SS (No. 1/MLB No. 1)

Yes, we know he struggled in his first taste of the big leagues and he hasn’t been firing on all cylinders back in Triple-A (though his .900 OPS is just fine). But we have to remember that he’s still only 20 and we believe in his his advanced approach and his ability to get to and grow into his power. He hit 12 homers and stole 24 bags as a teenager last year during his mercurial climb and still very much believe in his 60 power and speed grades. (Mayo, Callis & Dykstra - MLb.com - June 12, 2024) 

Topps has been producing stand-alone sets featuring Major League Baseball players as Garbage Pail Kids for several years now, but 2024 Bowman Chrome, which was released on Wednesday, Sep 10th includes a first-ever GPK insert set in a wider, more traditional product.

For example, there’s "Hovering Holliday". On his card he is depicted smiling up in the clouds holding a baseball bat while an exhausted oriole suspends him in mid-air with his feet. (Peck - Sep 11, 2024 - The Athletic)

Holliday started 2024 in Triple-A Norfolk despite fans clamoring for him to open the year with the big league club. We didn't have to wait long, as the O's made the call in early April, bringing Holliday up to Baltimore for his major league debut.

His first stint with the Orioles went poorly, as Holliday managed to collect just two hits in his first 36 plate appearances. He was striking out nearly 50% of the time and the Orioles decided that in the midst of what would be a tight division race all year, that Holliday could use some extra time at Triple-A.

When he returned at the end of July, things didn't get immediately better. He had some big moments and the plate discipline looked a bit better, but overall it wasn't as impressive as O's fans had hoped.

Could a swing change lead to a major breakout for Jackson Holliday? Interestingly, Holliday made a last minute change at the end of the year that could serve as a catalyst for a major breakout in 2025. Throughout his career, Holliday had a big leg kick in his swing. In some cases, that can help a player add power but it has the ability to mess with a player's timing if they can't perfectly repeat the motion.

Toward the end of September, Holliday had begun reworking his swing to eliminate the leg kick, and instead work with a much more subtle toe-tap. It may not look like much but small changes like that can make a major difference in a player's output.

Holliday deployed the toe-tap in just two games this year, those being on September 28 and 29. In those two games, he went 4-5 with a double and three walks. Small sample size alert, obviously. But that's quite impressive from a guy who'd been striking out at a far too great a clip, and failing to generate much impact on contact.

Will this change lead to better results over the long term for Holliday? That much is unclear, for now. But the early results are encouraging enough to be excited about the new process heading into 2025. (Tim Smart |Oct 9, 2024) In a handful of 2024 Triple-A games before the promotion, he blasted the competition for a .333/.482/.595 batting line. From July 31 onward, the Orioles played Holliday nearly every day. Across 50 games and 43 starts, he dropped a batting line of .218/.285/.365 - a .650 OPS, including five home runs.

Holliday is a lefthanded hitter who has a hit-to-all-fields advanced approach at the plate. He has natural feel for the barrel with easy bat speed, showing an impressive ability to drive the ball to the opposite field.

It's an easy argument to make that Holliday is the best pure hitting prospect in the game. His incredibly advanced approach at the plate led to him being one of just eight Minor Leaguers who walked 100 or more times in 2023, resulting in a .442 on-base percentage. He combines that discipline with a short left-handed stroke that delivers consistent hard contact and elite-level exit velocities. Still only 20 for the 2024 season, Holliday continues to add strength, and there’s confidence he’ll drive the ball more -- and over the fence -- with greater consistency. (Spring 2024)

Jackson has a 70 grade hit tool with 55 grade power. He has at least plus plate discipline. Those qualities allow him to control the strike zone and make consistent, high-quality contact. After a fair share of weak fly outs in his 2022 pro debut, Holliday sharpened his ball flight to more consistently hit crisp line drives to all fields in 2023. Holliday had a 45.5% hard-hit rate, up from 34.6% in his pro debut, while increasing his 90th percentile exit velocity from 99.4 mph to 102.5.

His continued physical maturation could help him develop above-average power, but if not he will be a doubles machine because of the quality of his contact. He has demonstrated an ability to backspin the ball and give it extra carry. The Orioles were impressed with the way he tapped into his pull-side power as the season went on, and Holliday didn’t sacrifice his all-fields approach to get to that. (Jon Meoli - Baseball America Prospect Handbook - Spring, 2024)

The combination of nature and nurture certainly come into play, with growing up around the game clearly helping Holliday’s overall skillset. He has an extremely advanced approach at the plate, and he showed it off by walking more than twice as much as he struck out during his debut last summer. He has a simple left-handed stroke he got back to after his swing got a little long last summer, allowing him make more hard contact than ever, with plenty of power coming organically from his swing. (BA - Spring 2023)

Holliday has a smooth, fluid swing that doesn't require maximum effort to create maximum bat speed, with good body awareness to make him adjustable and keep the barrel through the zone well. Holliday already boasts advanced strike-zone discipline, and the continued physical development his frame suggests is imminent could give him above-average power to go along with his plus hit tool. He handled velocity well in his pro debut, but the Orioles want him to continue overcoming expected challenges with velocity and advanced pitch shapes as he climbs the minors. (Jon Meoli - Baseball America Prospect Handbook - Spring, 2023)

Jackson looks like a plus hitter when he is focused on the opposite field gap and willing to go the other way, instead of ripping out on his front side and trying to hunt homers like he did over the summer of 2021.

Holliday has an advanced approach, no surprise given his roots, and a knack for putting the barrel on the ball. He usually makes consistent hard contact, though he didn't during the summer when he let his simple left-handed stroke get too long. After getting bigger and stronger, he hit the ball with more authority than ever this past spring, and he also looked more relaxed at the plate, letting his considerable power come naturally. (Spring 2022)

Jackson still has room to add more strength to a 6-foot-1, 180-pound frame and he could grow into above-average power in the future. He hammers hard line drives all over the yard.

Jackson has a slightly open stance and a high hand and elbow set-up. He shifts his while staying balanced throughout. He has a fluid stroke — a loose, whippy lefthanded swing.

2023 Futures Game: Best overall prospect- Holliday’s batting practice was impressive because he took it in a professional manner, as if he were preparing for a major-league game. He hit the ball to all fields and didn’t try to show off by attempting to do too much, like some prospects do at these events with so many eyes on them. He had a calm approach, hitting line drives all over the field while also demonstrating his power. He’s a special player with an incredible future. (Bowden - Jul 9, 2023 - The Athletic) 

The highlight of the night for last year's first overall pick came in the seventh inning when he swatted a triple off the center-field wall, plating two runs. The 19-year-old also stole his 21st base of the season in the sixth, showing off both his 70-grade hit and 60-grade run tool in short order.

The last time a Baysox player tallied a five-hit night was in 2019 when outfielder Cedric Mullins hit for the cycle. For Holliday, the five-hit performance was the latest in a string of impressive outings, including last Saturday, when he went 4-for-5 and swatted his second Double-A homer -- and ninth of the season in total. He followed that up with his 10th jack of the year the next day.

Seemingly on a nightly basis this season, the Orioles’ top prospect has continued to amaze. The five-hit night is his first for Double-A Bowie, but his third in total -- all the more impressive considering he is younger than nearly everyone he plays against.

If that isn’t enough, he’s tallied 29 multi-hit efforts in 88 games played this season. That means any given day that Holliday’s name is penciled in the lineup, there’s nearly a 33 percent chance that he will collect more than one hit in that contest. (Samson - Aug 11, 2023 - milb.com)

Jackson is a fine shortstop with soft hands, fielding the ball out front with both hands. He has solid hands and instincts, impressive athleticism and great carry and accuracy on his throws, which at times look like they are climbing into a second gear on the way to first base. He also shows a good understanding of where to position himself.  He has a 55 grade on his fielding and a 50 grade arm.

A plus runner who can steal a base, Holliday has more than enough range, good enough hands and actions and plus instincts to play shortstop for a very long time. The only thing that might be in question is his arm, which he’s worked to improve since entering pro ball. There’s a chance he’ll need to slide over to second, though that’s as much because of other Orioles personnel as it is any questions about his arm strength

Holliday is a gifted athlete who demonstrates the instincts of a baseball lifer both on and off the field, Holliday is loose and fluid at shortstop with the potential to be at least a plus shortstop and potentially a plus-plus second baseman, should the Orioles’ infield situation call for such a move. He’s a quick study defensively, can play one-handed, and has an advanced clock that means he doesn’t rush throws and often delivers them on time and on target.  (Spring, 2024)

With strength he added before his senior year, and with more to come, Holliday has also gotten faster and is a consistently plus runner. There’s an up arrow next to his arm strength as well and that, along with his improved quickness, means he should be able to play shortstop for a long time. His combination of pure tools and high baseball IQ could mean he moves through the system quicker than a typical prep player. (BA - Spring 2023)

Holliday is a true shortstop with all the skills and instincts to play the position at a plus 60 grade level, with a plus 60 grade arm and plus speed. (Spring, 2023)

Holliday has gotten faster as he has gotten stronger. He now flashes plus-plus run time and is a consistent plus runner. He's throwing better too, and his solid-to-plus arm strength and enhanced quickness give him a better opportunity to remain at shortstop. His high baseball IQ also helps his chances after many evaluators previously believed he was destined for second or third base. (Spring 2022)

Jackson is a 60 grade runner.

Holliday is a plus runner who was successful on 24 of 33 stolen base attempts in 2023. And he shows good instincts on the basepaths. He also has elite makeup, handling the pressures of his prospect status and expectations as well as anyone the Orioles have had in that position.

July 28-Aug. 4, 2023: In the minors, Holliday was on the 7-Day IL.