Anyone who has followed major league baseball in the last 45 years knows the best-ever shortstop for the Baltimore Orioles was Cal Ripken Jr. He was a second-round pick of the Orioles in the 1978 MLB draft and went on to a Hall of Fame career. 32 years later the Orioles made shortstop Manny Machado their first-round selection (third overall pick of the draft) in 2010. He was a four-time all-star with the Orioles, while he now plays for the San Diego Padres. Many would argue he’s bound for the Hall as well.

Since 2015, the Orioles have selected 12 shortstops in the draft and signed two other international shortstops. It seems the O’s GMs have been obsessed in selecting this many infielders at the same position. Perhaps they’ve been looking for the next Ripken or Machado.

That hope may finally be realized since Jackson Holliday was selected out of high school as the first overall pick of the 2022 draft. The highly-touted shortstop, with a major-league pedigree (his father is former MLB all-star Matt Holliday), has already progressed to Double-A. He was Jonathan Mayo’s (MLB.com) No. 12 ranked prospect prior to the 2023 season.

However, Holliday could have a huge challenge ahead of him if he advances to the majors within the next couple of years. He’s got several other high-round draftees already ahead of him on the major-league roster.

Jorge Mateo, acquired from the San Diego Padres during the 2021 season has been the starting shortstop for the O’s since his arrival. Gunnar Henderson, the second-round pick of the Orioles in 2019, was promoted to the big-league club earlier this season. With Mateo entrenched at shortstop, Henderson has been primarily playing third base. He’s already projecting to be a regular at one of the infield positions.

Then there’s Jordan Westburg, a first-round pick of Baltimore in 2020, who was also recently promoted. He’s primarily been seeing action at second base. Joey Ortiz, a fourth-round pick in 2019 who is on the Orioles’ 40-man roster, made his major-league debut this season. He’s been seeing action at shortstop, third base, and second base.

Even as the Orioles are contending for the AL East Division lead, they haven’t been shy about giving these youngsters a shot in the big leagues. They’re all contributing since they are capable of playing multiple positions.

But the odd thing is there are four more infielders at the Orioles’ Triple-A level who were high draft picks or international prospects as shortstop. Cesar Prieto, a Cuban native who signed in 2022, has somewhat flown under the radar because he wasn’t as well known as the top amateur draft picks. Others include Connor Norby, a second-round pick in 2020; Coby Mayo a fourth-round pick in 2020; and Caydn Grenier, a first-round pick in 2018. These prospects are being given an opportunity to play other infield positions, including first base, as well as the outfield. That strategy worked out well with another first-round shortstop in 2015--Ryan Mountcastle, who is the Orioles’ regular first baseman and sometimes DH.

As if that weren’t enough, the Orioles’ organization has two more high draft-pick prospects below the Triple-A level-- Anthony Servideo, a third round pick in 2020, and Collin Burns, a sixth-round selection in 2021, both of whom came out of the college ranks.

While there is a logistical logjam in the Orioles infield, in both the majors and minors, the situation actually puts the Orioles in a good position to acquire much-needed players at other positions by offering up several of these quality prospects. For example, pitching depth is always a necessity at this time of the season.

It seems far-fetched, but perhaps the Orioles can deal a couple of those high-profile shortstop prospects at the upcoming trade deadline for Shohei Ohtani, as a three-month rental. (Ohtani is a free agent after this season.) It would go a long way to ensure their berth in the playoffs and position them as a real threat throughout the postseason.

Oh, did I mention the Orioles picked two shortstops in the final two rounds, 19th and 20th, in this year’s draft? I guess their front office just couldn’t resist.