3 Jackson Holliday trades the Orioles can make to win 2025 World Series

After the Baltimore Orioles were swept out of the ALDS last season, GM Mike Elias opted against pushing all his chips in, nabbing Corbin Burnes but not doing a whole lot else to move the needle both over the offseason and at the trade deadline. The young core largely stayed intact, the payroll stayed clean and patience remained the overarching philosophy.

Now, though, that patience may have just gone out the window. Once again, Baltimore failed to win a single game in the postseason, suffering a Wild Card sweep at the hands of the Kansas City Royals this week. This time, it was the offseason that disappeared: The Orioles managed just one run on 11 hits across the two losses, getting next to nothing from stars Gunnar Henderson, Adley Rutschman and Anthony Santander.

Which begs the question: Where do Elias and the O's go from here? Another offseason on the margins feels untenable given the last two playoff failures, and there's still a ton of money to spend and a ton of young talent to dangle in a trade — highlighted by the former No. 1 overall prospect in baseball, Jackson Holliday. Holliday struggled in his first taste of big-league pitching, but he won't turn 21 until December, and it wasn't too long ago that he was torching every level of the Minors. His stock is still plenty high around the league, and if Elias is looking for a major talent upgrade, dealing Holliday would be the quickest way to check that box. Here are three blockbuster trades the team could pursue to finally get over the hump in 2025.

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3. Sandy Alcantara and Jake Burger, Miami Marlins

"Bloodbath" is the word getting thrown around in Miami right now, as new lead executive Peter Bendix goes about stripping the Marlins organization down to the studs and building a new one from scratch. So why not take advantage of the fire sale? Alcantara hasn't pitched since undergoing Tommy John surgery back in 2023, but he's expected to be good to go by Opening Day next year, and Miami almost certainly won't be interested in paying the righty the $34 million he's owed over 2025 and 2026. Alcantara is a legitimate ace when healthy, the perfect replacement should Corbin Burnes walk in free agency, and Burger (63 homers over the last two seasons) would give the team a corner-infield upgrade over the likes of Ryan Mountcastle and Ramon Urias.

2. Luis Robert Jr., Chicago White Sox

You could also target lefty Garrett Crochet here, but Baltimore's pitching feels a bit more stable than its lineup right now (assuming Grayson Rodriguez, Kyle Bradish and Zach Eflin can stay healthy next season). The outfield, meanwhile, is a bit of a question mark, with Cedric Mullins looking over the hill and Anthony Santander set for a payday in free agency. Robert Jr. could slide into Mullins' spot as the everyday center fielder, and he'd be a very good bet to bounce back after a down 2024. (You'd have a hard time staying motivated too on a team that bad, and there was next to no lineup protection.)

1. Vladimir Guerrero Jr., Toronto Blue Jays

All eyes will be on the Blue Jays this offseason. 2024 figured to be a make-or-break year, and the team flopped hard with a last-place finish. Now Guerrero Jr. and Bo Bichette are set to enter their contract years, with ace Kevin Gausman not far behind in 2026. Bichette wouldn't seem to be a great fit considering the presence of Gunnar Henderson and Jordan Westburg in the middle infield, but Guerrero Jr. would be an ideal solution to Baltimore's first base/DH quandary; Ryan Mountcastle and Ryan O'Hearn simply aren't good enough for a team with championship aspirations.