Jackson Holliday is making history before our very eyes

When the Orioles arrived at Draft Day 2022, their plan for the No. 1 overall was far from a sure thing—at least from the public’s perspective. When the Mike Elias-led front office stepped up to the plate for their first swing at the top overall pick in 2019, the choice was an easy one. Adley Rutschman was seen as a generational prospect in the mold of Bryce Harper or Joe Mauer. While there were some smokescreens suggesting that Bobby Witt Jr. or Andrew Vaughn might actually be the pick, Elias & Co. ended up doing the obvious, selecting Rutschman, and have reaped the franchise-changing benefits ever since.

Last year there was no obvious choice. Draft junkies and MLB front office viewed the likes of Druw Jones, Termarr Johnson, and Elijah Green as potential alternatives to Holliday with the first pick. Had any of those players been the pick, many members of Birdland wouldn’t have been surprised; some may have been even more excited. However, Holliday was the selection and since then he has done nothing but prove the Orioles front office correct.

Just this past week, in High-A Aberdeen’s series against Winston Salem, Holliday went 13-21 with two HRs, three doubles, three triples and a mind-boggling 14 RBIs. His latest display of ridiculous offensive prowess raised his numbers at High-A to a .395 average, a 1.229 OPS and 17 walks against only 15 strikeouts. Holliday has not just maintained his level of play since being promoted from Low-A Delmarva to Aberdeen, he’s arguably gotten better.

Holliday’s pre-draft profile painted his future as a hit-first shortstop whose only other true plus skill would be his speed. It was easy to envision him becoming a sort of left-handed hitting Tim Anderson. While that is a valuable profile, it doesn’t inspire the imagination and raise the ceiling on the franchise the way you’d hope a No. 1 overall pick could. Instead, the early returns from Holliday suggest that he can reach the heights of infielders like José Ramírez, Xander Bogaerts or even former Oriole Manny Machado.

Holliday’s early success also stands out that much more when juxtaposed against the players that the Orioles passed on in order to select him. Druw Jones—the teenage son of Braves legend Andruw Jones—was the player many preferred over Holliday. Jones went No. 2 overall and is currently plying his trade at Low-A, struggling to a .175 average with a surprising lack of power. He hasn’t played in a month due to a quadriceps strain. Johnson and Green, fellow teenagers who went No. 4 and No. 5, are also at Low-A, hitting in the .200s and struggling with strikeout problems.

With Holliday playing the way he is, it’s easy to imagine him ending the season at Double-A Bowie—facing pitchers who are five or six years older than him. The Orioles’ glut of infield prospects at Double and Triple-A suggests the front office won’t rush Holliday to Baltimore during his age-20 season in 2024. However, assuming Holliday continues to progress at a similar rate, he may simply be too good to keep him in the minors next season.

The question then becomes, what does Holliday improving leaps and bounds at such a rapid rate mean for the franchise? For one, it means that the Orioles could have accomplished something that so many franchises failed at: fully capitalizing on multiple No. 1 overall picks.

This century, five franchises were in the same position of the Elias Orioles: making two No. 1 overall picks in a four-year period. The Rays were the first team with such an opportunity, selecting David Price No. 1 overall in 2007. While Price would go on to make four All-Star appearances and win a Cy Young for Tampa, the No. 1 pick that joined him was much less successful. Shortstop Tim Beckham, taken No. 1 overall in 2008, ended up producing more WAR in two seasons for the Orioles than in parts of four seasons for the Rays.

The Astros had a similar pattern of success with their three consecutive No. 1 overall picks between 2012 and 2014. With Elias as scouting director, Houston struck gold with its first attempt, taking shortstop Carlos Correa at the top of the 2012 draft. Their next two attempts were big whiffs in pitchers Mark Appel and Brady Aiken. Appel never appeared for the Astros in the majors and Aiken didn’t sign due to medical concerns.

Of the other four franchises, only the Nationals found success with both of their No. 1 overall selections, taking Stephen Strasburg and Bryce Harper back-to-back in 2009 and 2010. The second most-recent addition to this group is the Detroit Tigers after they selected Casey Mize in 2018 and Spencer Torkelson in 2020—both of whom have struggled to find success in their brief MLB careers.

The Orioles are undoubtedly ahead of the curve when it comes to their rebuild producing success at the major league level. After all, just one year after Rutschman made his MLB debut, the O’s are currently the second-best team in all of baseball. However, what Holliday represents is the ability for this rebuilt franchise to continue to find new levels of success by the team evolving from within.

Most of the time, when a team graduates prospects the level of Adley, Gunnar Henderson and Grayson Rodriguez in the span of 12 months, the farm system is devoid of elite level difference makers. Instead, the Orioles have a player in Holliday who is likely to succeed Rutschman and Henderson to become Baltimore’s third No. 1 overall prospect in three years.

Undoubtedly a time will also come when the Orioles front office cashes in some of the prospects we’ve come to know and love, the same way the Astros cashed in on their prospects to get Justin Verlander and Gerrit Cole, or the Nationals emptied out their farm system to rework their bullpen ahead of their eventual World Series run.

However, as the Orioles looked primed to count themselves among baseball’s best teams for the foreseeable future, they do so knowing they have one more bomb to drop on the baseball world.

Baseball is generally seen as a game of failure. The drafting and developing of prospects is perhaps more fraught with failure than any other aspect of the game. When the O’s drafted Jackson Holliday, most expected he’d be good enough to make a difference at the majors—but there was every chance he’d instead fail. Now, he’s showing that he can be the difference maker that keeps Baltimore competing for titles year after year. Where most teams would feel lucky to strike gold at the very top of the draft once, the O’s appear to have found two golden players with their No. 1 selections.