CONFIRMED DEAL: The New York Yankees formally declare the trade of their best-veteran left-hander,, to the Baltimore Orioles for a $120 million, five-year contract.

BALTIMORE, MARYLAND - SEPTEMBER 21: General Manager Mike Elias of the Baltimore Orioles watches batting practice before the game against the Detroit Tigers at Oriole Park at Camden Yards on September 21, 2022 in Baltimore, Maryland. (Photo by Greg Fiume/Getty Images)

When exactly will the Orioles wise up and call up Jackson Holliday?

Here is our best guess as to when the Orioles could call up Jackson Holliday.

When the Baltimore Orioles made the decision to not carry Jackson Holliday on their roster for Opening Day, fans were understandably frustrated. Not only is Holliday widely considered to be the best prospect in baseball right now, but he also dominated in spring training and many assumed that it was a formality that he was going to make the Opening Day roster.

The Orioles’ reasoning wasn’t without merit. Holliday didn’t have a lot of experience against top level lefties, nor did he have a lot of experience playing second base, which is what he would have to play in Baltimore. While the more cynical fans out there feel like the Orioles are simply manipulating Holliday’s service time, there are real arguments for holding him down in the minors for a little while.

Baltimore Orioles v Pittsburgh Pirates

However, with Holliday torching the Triple-A competition thus far in 2024, it is fair to wonder when the Orioles could make the decision to call him up.

Multiple factors are in play regarding Orioles’ Holliday call-up decision

First and foremost, Baltimore needs to be convinced that Holliday is ready. By their own standard, that means seeing significant action against lefties and getting lots of reps at second base. So far, he has played a pair of games at second, and it is a safe bet that they will probably want him to play around 15 games or so there to feel fully comfortable. Plate appearances against lefties are somewhat outside of the organization’s control, but he did face a good one in his first series in Mason Montgomery and took him deep, so everything is on track there.

Baltimore Orioles v Pittsburgh Pirates

Second is team need, and that is where things get sketchy. The decision will be clear if the Orioles aren’t getting much in the way of production out of second base. However, both Jordan Westburg and Jorge Mateo are off to very decent starts at second base for the Orioles, and calling up Holliday is probably going to cost Baltimore Mateo or Ramon Urías, as both of them are out of minor-league options. To make that move, the Orioles are going to need some assurance that Holliday would be an actual upgrade, and might want to wait a bit until other teams’ rosters are entrenched to potentially float Mateo/Urias through waivers unmolested.

Baltimore Orioles v Pittsburgh Pirates

Finally, we do come to the service time considerations, which are a real thing and will certainly be on the Orioles’ minds when making a decision on him. However, it isn’t as simple as holding Holliday down until the end of April and getting an extra year of service time for him. The Orioles will also probably want to consider that if Holliday is on the big league roster for 172 or more days in 2024 and he finishes in the top two of Rookie of the Year voting, Baltimore gets an extra draft pick. The Orioles are well aware how that could be a big deal, as they got an extra pick thanks to Gunnar Henderson’s ROY campaign last season.

When will Orioles promote Jackson Holliday for MLB debut? Our best guess is…

Baltimore Orioles v Pittsburgh Pirates

Knowing all of that, plus the fact that it is extremely likely that the Orioles would want to debut Holliday in front of a home crowd against a soft opponent, Baltimore’s series against the Athletics on April 26-28 sticks out like a sore thumb. Oakland is truly terrible, it is a weekend home series, and the timing should work out for everyone involved. We shall see if the Orioles actually follow through with it.

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