The Baltimore Orioles entered the 2024 offseason with high hopes, aiming to build on their breakthrough 2023 season. After finishing with a 101-win record and a playoff berth, expectations were elevated, and many believed the team would make key acquisitions to bolster their chances for continued success in the AL East. However, as the offseason progresses, the Orioles’ inability to make significant moves has raised questions about their strategy and whether they might need to explore trading one of their top prospects—Jackson Holliday—sooner than expected.

 

Holliday, one of the most highly touted prospects in baseball, was drafted first overall by the Orioles in 2022. The 19-year-old shortstop has quickly become one of the crown jewels of Baltimore’s farm system, known for his exceptional bat-to-ball skills, plate discipline, and defensive potential. His rapid ascent through the minor leagues, including a standout 2023 season, has made him a centerpiece of the Orioles’ future.

 

However, as the Orioles’ offseason moves have fallen short of expectations, the possibility of moving Holliday in a trade is increasingly being discussed. Baltimore’s front office had hoped to address key areas of need, especially the pitching staff, but thus far, their biggest moves have been modest. While they’ve made some small additions and retained core pieces, the Orioles’ failure to land a top-tier starting pitcher or a high-impact bat has left the roster looking less formidable compared to other contenders in the AL East.

 

The Orioles’ pitching staff, while solid, still has gaps that need addressing. The starting rotation, in particular, could use an ace-level pitcher to compete with the likes of the Yankees, Rays, and Blue Jays. Though the team made a strong push last season, many experts have questioned whether their current rotation, led by Kyle Gibson and Dean Kremer, can hold up over the course of a full season, especially in a division as competitive as the AL East.

 

As a result, there’s growing speculation that the Orioles could use Jackson Holliday as the centerpiece in a trade for an established pitcher or a veteran hitter who could immediately contribute. While the Orioles have a deep farm system and could certainly explore other avenues, Holliday remains the most attractive trade chip. His value is incredibly high, and with a wealth of talent already in place at the big league level—particularly in the outfield and infield—the Orioles may feel that dealing him could expedite their efforts to contend for a championship sooner rather than later.

 

The Orioles’ reluctance to part with Holliday has been clear, given his status as a potential franchise cornerstone. However, the longer the team goes without making a splash in free agency or a trade, the more plausible it becomes that they will move him. Front offices in competitive markets tend to lean toward bold decisions when the championship window is open, and with a young team that is on the brink of greatness, it’s easy to understand why the Orioles might feel the pressure to make a big move.

 

While a Jackson Holliday trade would certainly be a tough pill for the fanbase to swallow, it’s a decision that could pay long-term dividends if it leads to the acquisition of a legitimate ace or proven hitter to help the team contend now. Given the Orioles’ position, the trade market might be the best way for them to address their immediate needs and make a push for a title in 2024.

 

In conclusion, while Jackson Holliday’s future with the Orioles has long been seen as part of their long-term plans, the team’s inability to secure key offseason upgrades has shifted the conversation. A trade involving Holliday is more likely than ever, and Orioles fans may soon be faced with the reality that their prized prospect could be the piece that helps bring the team closer to a championship. Time will tell if Baltimore is willing to part with their future star to secure their present success.