This Jackson Holliday trade would be Orioles' smartest deadline move this summer

Let's go ahead and rip the band-aid off here. The Orioles should trade Jackson Holliday.

I know what you're thinking, and that's fine. But let's walk through it. The team won the AL East last year for the first time since 2014, and just the second time since 1997. They're currently in a tight race with the Yankees for the division and they need all the help they can get.

The Orioles' window of contention is as open as it's ever going to be, and they shouldn't wait until mid-summer to bolster the roster.

The thing about Jackson Holliday is that while he's an elite prospect, he's not helping the Orioles win right now. And worse, he's blocked at his natural defensive position.

Gunnar Henderson is a budding superstar and he's obliterating the league right now. Henderson is top 10 by OPS and wRC+, he's second in baseball with 16 homers, and he's doing so with excellent defense at short.

What's more is that all of Henderson's expected stats match the performance, which means there's no sign of him slowing down. Plus, Henderson won't hit free agency until after the 2028 season, so he'll be in Baltimore for a while.

Unfortunately for the Orioles, Holliday is going to provide the most value in the majors as a shortstop. But at this point, it doesn't make sense to move Henderson off the position. There's been some talk of shifting Holliday to center field or second base, but those moves are easier said than done, especially mid-season.

The O's also have Jordan Westburg raking in the majors, and Connor Norby and Coby Mayo in the minors looking like future studs. If there's one team in baseball that can stand to trade the best prospect in the sport, it's this one.

Orioles stud Jackson Holliday will never have as much trade value as he does right now

The thing is, there's such a small subset of players who make sense in a trade like this. But there's at least one out there, and the Orioles should strongly consider it.

For the past three years, Tarik Skubal has been one of the best pitchers in baseball on a rate basis. The innings total hasn't been there, but in 258 innings since the start of 2022, Skubal has a 2.47 FIP with 297 strikeouts to just 56 walks.

The lefty is in the thick of the AL Cy Young race, has some of the nastiest stuff in the majors, and has the results to back it up.

2024 is Skubal's first year of arbitration eligibility, and he won't be a free agent until after the 2026 season. Building a postseason rotation around Skubal and Corbin Burnes will terrify opposing teams. And since Skubal has 2.5 years of control left, it's an insurance policy if Burnes decides to leave in free agency this winter.

It's probably not a one-for-one deal. Maybe the Orioles have to send Cade Povich or Enrique Bradfield along with Holliday to get the deal done. But the O's are in a position where they need to win now, while the Tigers are in a spot where it makes sense to add an elite long-term option at the expense of wins this year.

Moving the number one overall prospect is a bit unprecedented, but if the Orioles can use Holliday to put themselves in a better spot for October, it's a risk worth taking. Flags fly forever, and it's been too long since this team has hung a new World Series banner at Camden Yards.