What is the Right Course for the Orioles at the Trade Deadline?

To sell or not to sell – that is the question!

Two weeks ago, the notion that the Baltimore Orioles could claw their way back into playoff contention was ridiculous. Sitting at 16 - 34 and having won only one series the entire season, it was clear to experts and fans alike that a 2025 reboot was required to contend in 2026. Anyone not named Henderson, Rutschman, Cowser, or Holiday would be on the trading block, partly as a salary dump and partly as a quick avenue to reload the farm system.

Fast forward to the first week in June, and that might still be the correct notion, but it is no longer the only one. The O's have won 9 of their last 11 and 6 straight, putting their record at 25 – 36 and culling their wildcard deficit to 7.5 games. While it would still take a Herculean second-half effort to garner their 3rd straight postseason appearance, the possibility no longer seems absurd given the recent turnaround, the return of key players from injury, and the resurgence of the starting pitching.

The young crowd will not remember, but the Orioles have been here before. Most forget that in the mid-90s, the free-spending Orioles had the highest payroll in baseball, but their 1996 team was significantly underperforming and was 12 games out of first place as the trade deadline approached. Then General Manager Pat Gillick recognized the team's deficiencies and decided it was time to wave the white flag and deal established players (and pending free agents) like Bobby Bonilla and David Wells for young talent to build for the future. Owner Peter Angelos – ever the businessman and concerned about potential impact at the gate – vetoed Gillick's plan and mandated that the O's stay the course. The Orioles went 37 -22 the rest of the way and secured a wild card spot, validating the directive from Angelos.

 Or did it?

The Orioles ultimately lost to the Yankees in the ALCS. Bonilla and Wells walked via free agency at season's end. Although they made another ALCS run in 1997, the Orioles endured 14 consecutive losing seasons from 1998 to 2011, as Angelos reigned in spending and the depleted farm system produced little. The big second half in 1996 was merely fool's gold, resulting in years of misery in Charm City.

Which brings us back to the 2025 Orioles. Sell or stand pat and take your best shot? Valid arguments exist for each. There is no questioning the position player talent when the team is healthy. 2024 AL Rookie of the Year runner-up Colton Cowser just returned from a fractured thumb, and the team is expecting Jordan Westburg, Cedric Mullins, Ramon Laureano, and Ryan Mountcastle back soon. That group, joining Gunnar Henderson, Ryan O'Hearn, Jackson Holiday, and Adley Rutschman, makes for a playoff-caliber offense.

The big question is, can the starting pitching continue its recent success? On paper, it is not a formidable group. Zach Efflin has a track record of sustained success in the American League, and Charlie Morton has turned the corner after a terrible start to the season. Can Dean Kremer, Tomoyuki Sugano, and Cade Povich continue to keep them in games? That is anyone's guess.

Of course, hope springs eternal, and the most optimistic of fans can envision Kyle Bradish, Tyler Wells, and Grayson Rodriquez getting healthy and pitching meaningful innings for the team in August and beyond – but anyone telling you that is a sure thing is a charlatan. 'If this, if that' is no sure foundation for success, but it is what the Orioles face.

Maybe the right answer is a hybrid approach. It worked for the Tigers last year. There were abundant rumors that everyone, including ultimate Cy Young winner Tarik Skubal, was available in a purported fire sale, but that didn't happen. The Tigers did not stand pat, however – dealing Jack Flaherty, Andrew Chafin, Mark Canha, and Carson Kelly for a group of prospects they hope can help down the road. Despite the subtraction of those veteran contributors, the Tigers took off behind Skubal and a young nucleus of position players that took advantage of increased opportunities.

It is not hard to envision the Orioles doing the same. Players like O'Hearn, Mountcastle, and Cedric Mullins are all pending free agents – and all could help playoff-contending teams down the stretch. When the team is fully healthy, those guys will be between top prospects Coby Mayo and Heston Kjerstad — and not just for playing time, but possibly for roster spots. It is time to give those kids a closer look, since they are supposed to be part of the next championship team in Baltimore.

Of course, there is additional intrigue in Samuel Basallo, the number-one catching prospect in baseball. Basallo is still in AAA because you don't bring that type of prospect up to be a backup. A trade of either (or both) O'Hearn and Mountcastle opens the door for Basallo's call-up, allowing him to not only spell Rutschman behind the plate but to play first base and DH on the days Adley is the backstop.

It is all speculation at this point, and the reality is that General Manager Mike Elias has not exactly nailed the trade deadline since arriving in Baltimore. While he won't get any interference from ownership as Gillick did three decades ago, there is no reason to expect him to make a splash deal at the deadline to further push the Orioles up the ladder. He may surprise everyone this year. This may be the year you deal some veterans for prospects. Maybe this is the year you deal a rising star to get a number one starter to front your rotation. Maybe.

Time will tell, and to be fair, there is a lot of baseball between now and the deadline. The Orioles' play between now and the deadline will likely dictate Elias' course of action. Patience is hard, but there is a reason it is a virtue. These O's need to ride out June and see if they can keep closing ground on the leaders. If they do, then the onus is on Elias to take bold action (yes, gamble too) and see if he can push the O's back to the playoffs to take a crack at the first World Series title since 1983. As always, time will tell.