Rare Bird: Jackson Holliday Speeds Through Minors To Win 2023 MiLB Player of the Year Award


Image credit: Jackson Holliday is Baseball America's 2023 MiLB Player of the Year. (Photo by G Fiume/Getty Images)

The draft is not a crapshoot. It’s not a random dice roll that determines success or failure. Teams devote thousands of hours from dozens of people to get draft decisions right.

But there is always some luck involved. Sometimes a team picks at the top of a draft with a franchise player available. Other times, there’s no franchise player to be picked. Sometimes, teams get it wrong.

Ken Griffey Jr., Chipper Jones, Joe Mauer and Bryce Harper proved to be the type of No. 1 picks that playoff teams are built around.

Other times, Matt Bush, Tim Beckham or Luke Hochevar are drafted first overall.

Just 16 months after being drafted first overall in 2022, Jackson Holliday looks like he belongs with the group of franchise players.

Holliday was the 2022 BA High School Player of the Year heading into the draft before the Orioles drafted him first overall.

A year later he was in Double-A. He finished his first full season at Triple-A Norfolk after blitzing through four levels of the minor leagues in 2023. 

Holliday hit .323/.442/.501 and led the minors with 113 runs scored and ranked fifth in both on-base percentage. He walked almost as much as he struck out. He’s proven a reliable and solid defender at shortstop and second base. He swiped 24 bases while showing off his plus speed.

And he’s impressed by playing with the approach and intelligence of a savvy veteran, even if he’s a baby-faced 19-year-old.

“I mean, just look at him. I know he’s 19, but he passes as 16,” Norfolk manager Buck Britton said, “but the skill set is off the charts.”

Holliday’s outstanding season, which saw him dominate as a teenager while spending half the season at the upper levels, earned him our Minor League Player of the Year award. 

Holliday becomes the second consecutive Orioles player to be named Minor League POY, following shortstop Gunnar Henderson last year. Orioles catcher Matt Wieters previously won in 2008.

Holliday also becomes the fourth player to win both High School and Minor League POY, joining Joe Mauer, Byron Buxton and Bobby Witt Jr.

It was the right choice. The obvious choice.

But it wasn’t obvious heading into the draft.

“It’s a very, very high stakes game (picking 1-1), because if you happen into a good one, you’re going to change your franchise. If you blow it, you’re gonna have a lot of people lose a lot of sleep for a long time,” Orioles executive vice president and general manager Mike Elias said.

 “And you don’t have a crystal ball. Sometimes these things look so obvious in hindsight, but I can promise you at the moment, there’s no scouting department that doesn’t have its doubts about any of these players.”

Every other prospective pick at the top of the 2022 draft has failed to come close to what Holliday has done. Outfielder Druw Jones went No.2 overall in 2022 and has yet to get out of Low-A. He’s spent most of his pro career on the injured list. 

Righthander Kumar Rocker, the third pick, is on the sidelines recovering from Tommy John surgery. 

Second baseman Termarr Johnson, picked fourth, did a good job hitting for power and getting on base in a season split between Low-A and High-A, but he also hit .244.

Outfielder Elijah Green, who was picked fifth, has struck out 41% of the time as a pro.

Third baseman Jacob Berry, picked sixth, hit .233/.284/.388 with nine home runs between High-A and Double-A.

Less than two years after being picked first overall, Holliday is the favorite to rank No. 1 on the Top 100 Prospects list next spring. He looks likely to reach the majors in the near future. He gives the Orioles yet another potential franchise player on a team that has been producing them at a furious pace in recent years.

Just 22 months ago, however, the idea of Holliday becoming the top pick in the 2022 draft seemed highly unlikely.

Good Turns Into Great

As New Year’s Day 2022 arrived, Holliday, the son of all-star outfielder Matt Holliday, seemed likely to be a first-round pick, but it would have been hard to find anyone who saw him as the top pick.

Holliday ranked No. 32 on the BA ranking of top draft prospects coming out of the summer.

Holliday himself knew it. He’d shown flashes of his potential, but when matched up against the best of the best in summer showcases, he’d strung together too many unimpressive at-bats.

“I didn’t play near as well as I wanted to (over the summer). My swing got a little out of whack. I kind of had some bad tendencies,” Holliday said. “In high school I was able to get away with it. Then, going into the summer, I kind of got exposed a little bit.”

Holliday started lifting weights more intensely in the lead-up to his senior season. He got stronger. He got faster. He started to throw better. But none of that would have mattered much without a reworked swing.

“I was just sitting in the living room one day messing around with my swing,” Holliday said. “I just wanted to make it more simple. Just kind of start like where I wanted to load from. Everything kind of kind of clicked from there.

“(Before) I was over my head (with the bat in the pre-pitch setup). I was getting super turned in. My only way out of that was to over-rotate, and I was coming underneath the ball. I was either clipping it to left field or hitting it pull-side on the ground. There’s no hits in either of those places. So I just really cleaned up my swing.”

Simple quickly proved to be better.

“OK, I’m gonna pick up my leg, and whenever I pick up my leg, my hands automatically load,” Holliday said. “So that’s kind of how I went about it. And during practice one day I was like, ‘Screw it, let’s do this,’ and I was driving them all over the place, hitting home runs all over the field. I’m like, ‘Well, I guess I guess this will work.’ ”

In his first scrimmage for Stillwater (Okla.) High with the new swing, Holliday homered twice. He hasn’t stopped hitting since. He set the national high school record with 89 hits in his senior season, topping J.T. Realmuto’s record.

“This is a kid who made a huge leap,” Elias said. “In the spring, fortunately for us, and I think most of the industry, the area scouts, the boots on the ground, saw it pretty early and rang the bell. Our guys in Oklahoma, Ken Guthrie and Jim Richardson, were not shy about revising their projection from the summer and saying this is a guy that we need to get in here (to see) for the No. 1 pick.”

The Orioles got numerous looks at Holliday that spring. In the span of six months he’d gone from probable first-rounder to a clear choice for No. 1 overall. 

“Anything you can do, he did it,” Elias said. “Then that’s where the scouting comes in. Every evaluator we sent in there, and every evaluator that we had studying his video remarked on his eyes and the barrel accuracy and then also the fact that it’s a mechanically clean swing.”

Quick Impression

Holliday began impressing Orioles officials from his first day in the organization, but in spring training this year he started showing hints of being special.

Holliday hit .429/.556/.500 in 18 Grapefruit League plate appearances. Veterans and coaches also noticed how well he carried himself. He was assured, but not arrogant. He looked and acted like he belonged.

“He looked the part in spring training,” Elias said. 

“I think, growing up in the clubhouse with my dad and being around a bunch of big leaguers, that part is honestly pretty easy for me,” Holliday said.

That fast start carried over to the season. Holliday began the season by getting on base in each of his first 40 games. Pitchers soon learned that he was infuriatingly consistent in his at-bats. He never had back-to-back games in 2023 where he failed to reach base. 

He was kept off base in just nine of his 125 games. Two of those nine came when he went 0-for-1 in pinch-hitting appearances. He had five games when he reached base five times and one when he reached base six times.

”The combination of swinging at strikes, being OK with taking your walks, as well as a really elite contact skill and being a plus runner . . . When you can walk, when you can put the ball in play and you can run, you’ve got a pretty good chance to get on base on a somewhat regular basis,” Orioles farm director Matt Blood said.

That combination forced the Orioles to put him on an extremely aggressive promotional path. In Class A, Holliday’s advanced batting eye meant he was walking (64) almost as much as he struck out (67). After he went 7-for-9 with two walks and one strikeouts in his final two games at High-A Aberdeen, the Orioles sent Holliday to Double-A Bowie. 

Holliday’s goal had been to reach Double-A before the season ended. He was there by mid July.

“The ability to make proper swing decisions, and the ability to make consistent, solid contact . . . You have those two things as a 19-year-old, you’re going to have success,” Blood said. 

“When I saw him last year in Low-A when he just got moved up after being drafted, teams were intentionally walking him in important situations in the game . . . And then I’m watching this year, and I saw it happen in High-A, and I saw it happen in Double-A. Teams (were) pitching around him or intentionally walking him. And it’s like, ‘Well, you know, this happens enough (that) he needs to move up.’ ”

Within the next month, he had another five-hit game and a three-walk, two-hit game for Bowie. He reached base four or more times in four of his 18 games at Triple-A Norfolk.

“He’s gotta go somewhere where they’re going to challenge him and where he’s gonna get the proper practice that he needs. And right now, that’s Triple-A,” Blood said. “You just sort of second guess yourself in the sense that you don’t see this very often. But he’s proving to us that he’s beating the level where he is and he needs better competition.”

Holliday finished fifth in the minors in on-base percentage. The four hitters ahead of him were all 25 years old or older.

“The fact he does that at age 19, that is what’s amazing about him. He’s 19 and he’s doing it. That’s what is exceptional about him,” Blood said. “Because he’s doing it at such a young age and he’s stacking these development experiences on top of each other that allow him to reach levels that others can’t because they are doing it at older ages.”

More To Come

Holliday’s exceptional skills are best appreciated by watching him game after game. 

One game may not make an impression, but watch Holliday for a week and you’ll get an appreciation for what makes him special.

Holliday is a plus runner. He has above-average power. He’s at least an average defender at shortstop. There’s no significant weakness to his game. Even his average arm plays up because of a quick release. 

But Holliday’s skills stand out. He has a headiness about everything he does that hints at the fact that he’s grown up immersed in the game. If a pitcher tries to attack Holliday right away, he’s ready. He hit .486/.486/.662 when he put the first pitch of an at-bat into play. 

But he is even more comfortable drawing out at-bats. If a pitcher nibbles, Holliday will wait him out. He swings at strikes and he usually makes contact.

“He takes his shots when he wants to take his shots early in the count, but when he gets two strikes, he goes to another level,” Britton said. “For him to be 19, to have this little experience as he does in professional baseball, and to be able to command the zone and not panic when his back’s up against the wall is, I think, is part of what makes him special.”

In an era when pithers force hitters to swing and miss at high rates, Holliday is driven by the thought of putting the bat on the ball. 

“I’m very competitive. And I hate striking out. So I think there’s an extra gear that I kick in, especially with two strikes,” he said. “No one likes striking out, especially whenever you’re trying to help your team win. 

“I’d rather put the ball in play and try to make something happen, because I feel like I can run a little bit. Good things happen whenever you put the ball in play.”

The scary part is: There might be more to come.

Holliday is a top-of-the-order hitter—for now. His ability to string together quality at-bats is currently more notable than his power. But he’s 19.

“What 19-year-old doesn’t get stronger?” Elias said.

Holliday just finished what would have been his freshman year in college by hitting .267/.396/.400 in Triple-A. He’s already consistently hitting the ball hard—his 91 mph average exit velocity ranks among the best in the minors for teenagers. But he’s likely to get stronger over the next decade. He will still be in his 20s during the 2033 season.

“I think I want to get a lot stronger for next year,” Holliday said. “Being around these guys, you see how hard they hit the ball. And even watching big league games. I mean, guys hit the ball so incredibly hard. You’ve got to be able to hit the ball hard to get hits in the big leagues. So I’m excited for this offseason to be able to get stronger, faster, and be able to impact the game with a little bit more power.”

Holliday will also likely improve defensively. He’s a capable infielder, but on a team that has Henderson and Joey Ortiz, he’s not as rangy and doesn’t have as strong an arm as some of Baltimore’s other shortstop options. Elias called him an average MLB defender at shortstop right now, but Henderson and Ortiz are both plus or better defensively.

“I know I need to be a better defender. To play in the big leagues, you have got to be able to play a key position. And that’s what I want to do,” Holliday said. “I want to be able to play in the middle of the field for a long time.”

Normally with a 19-year-old, these would be the type of long-term issues that will be sorted out over the next few years of development.

Holliday has accelerated that timetable. He’s already played in Triple-A. 

“When you’re in Triple-A and you’re performing, you are a phone call away and, so I wouldn’t rule anything out,” Elias said.

Holliday will head to spring training next year competing for a spot on the big league roster. Whether he breaks camp on the MLB roster or not, it’s hard to imagine a scenario where a healthy Holliday doesn’t play in Baltimore next season.

If he ranks as the No. 1 prospect heading into 2024, he will become the third Orioles prospect in a row to do so, following Henderson and Adley Rutschman. That’s never happened in the 35-year history of the BA Top 100 Prospects.

It’s easy to say that the Orioles are succeeding because they have picked at the top of the draft. But picking the right player and developing them properly isn’t a given.

Sometimes, you pick Ken Griffey Jr. Sometimes, you pick Mark Appel.

A year and a half after they picked him, the Orioles appear to have chosen very wisely.

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