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To Trade or Not to Trade? The Baltimore Orioles Must Decide the Fate of Top Prospect Jackson Holliday

The Orioles, who lead the American League East by 1 1/2 games going into Wednesday, could trade some of their top prospects before Tuesday’s trade deadline in order to bolster their underutilized starting pitching staff.

But it is nearly hard to imagine a situation in which Jackson Holliday is involved.

Not only is Holliday the top prospect for the Orioles. He is baseball’s top prospect overall. Over the last 30 years, there has only been one trade involving the consensus top MLB prospect, a sign that organizations are becoming less willing to part with elite young talent.

Yoán Moncada, Michael Kopech, Luis Alexander Basabe, Victor Diaz, and the White Sox traded pitcher Chris Sale to the Red Sox prior to the 2017 season. At the time, MLB.com and Baseball America ranked Moncada as baseball’s best prospect. Dave Dombrowski, the general manager of the Red Sox at the time, made the decision to provide Boston with the long-term front-line starter it needed. (At the time of the deal, two options would have put Sale under team control for a total of $38 million over the following three years.)

With Sale, the Red Sox won the 2018 World Series. At the time, the White Sox trade was highly appreciated, and Chicago appeared to have added a substantial amount of value over the course of several years. Chicago was given the advantage in the trade even in 2021, according to the website Baseball Trade Values. However, it is now known that Moncada, 29, is not the type of franchise-altering talent that was anticipated; instead, he has a career WAR of 14.5.

Will Holliday have that type of influence on the game? Under general manager Mike Elias, the Orioles front office has been quite successful in selecting and developing young players, especially those drafted outside of the first round. Elias selected Holliday with the first overall pick in 2022. Gunnar Henderson, a 23-year-old who could be the American League MVP, was selected with choice No. 42. Holliday, 20, is the 20-year-old son of former major leaguer Matt Holliday and is expected to be an All-Star with the Orioles, where he might play opposite Henderson for many years to come. Holliday received a record-breaking $8.19 million bonus from Baltimore for a high school athlete.

There is not a pitcher available at this year’s deadline worth dealing Holliday for, despite the Tigers starter Tarik Skubal being frequently discussed. This is assuming the Orioles have not changed their assessment on Holliday internally.

Holliday struggled in his meager 10 games in the major leagues earlier this season, and it appears that his name has surfaced in trade rumors now that he is at Triple A. Numerous big-league players have struggled on their first call-up.

The Orioles, who disappointedly missed the postseason after round one last year, are under a lot of pressure to bolster their pitching staff. But even talking about dealing Holliday—who ought to be considered practically untouchable—seems crazy.

Elias has largely showed prudence when it comes to moving prospects, making only slight trades at last year’s deadline in order to obtain starter Jack Flaherty and reliever Shintaro Fujinami. Elias has rebuilt the Orioles faster and better than most observers could have predicted. If Elias and the Orioles were to become so conservative once more, it would be surprising, especially since Elias just informed reporters that the team’s new ownership has approved salary increases.

However, the Orioles can improve their pitching staff in a number of ways without having to trade Holliday. Their agricultural system is the best in the game. If anyone is made available in the next six days, a combination of Connor Norby (No. 5), Coby Mayo (No. 3), and Samuel Basallo (No. 2 prospect for Baltimore) should be in the conversation. Skubal, Garrett Crochet, or Nathan Eovaldi, should the Rangers decide to sell, might be among them. Players currently on Baltimore’s roster, such as Ramón Urías and Jorge Mateo (whose health is uncertain following a collision on Tuesday), might potentially be dangled. Although Kyle Stowers is now at Triple A, he has had ups and downs with the Os on multiple occasions and may be a reliable major leaguer in another league.

In the coming days, Elias and the front office team will have to make some difficult choices regarding how to strike a balance between the organization’s long-term viability and winning in 2024. Holliday, though, is expected to play for Baltimore once more this season, so he is not simply a part of the Orioles’ future.

The best prospects will be traded in the coming week, and if the Tigers decide to trade Skubal, it is likely that the team’s top prospect will be included in the trade. The Padres traded C.J. Abrams, their top prospect, before the season and Robert Hassel III in the middle of the season to acquire Juan Soto in 2022. (At the time, neither player was thought to be among the top five prospects in baseball.) Teams may feel under pressure to play their finest players at times.

But the Orioles should not have to. Despite deference to Skubal, Crochet, and any other players who might be available, Basallo and Mayo are both among baseball’s top 15 players, and as of this year’s deadline, there is not a player near to Soto’s value available.

Baltimore should have a significant trade deadline this year. In no way should Holliday be included.

(Top photo: G Fiume / Getty Images)

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