What Is Baltimore Orioles' Biggest Question Entering Winter Meetings?

The Baltimore Orioles face some big questions going into the winter meetings, but this one could be the biggest.

Oct 1, 2024; Baltimore, Maryland, USA; Baltimore Orioles pitcher Corbin Burnes (39) throws a pitch in the second inning against the Kansas City Royals in game one of the Wild Card round for the 2024 MLB Playoffs at Oriole Park at Camden Yards. / Tommy Gilligan-Imagn Images

The Baltimore Orioles are heading into the Winter Meetings with things being fairly quiet on their front. 

Over the past two seasons, Baltimore has had a lot of success during the regular season. They were able to win the American League East in 2023 and followed that up with a 90+ win in 2024. 

While Baltimore has had a lot of success during the regular season, that hasn’t translated into postseason success just yet. The Orioles tried to fix that last offseason when they pulled off a blockbuster trade to bring in Corbin Burnes. However, despite him pitching well, it wasn’t the missing piece to get them over the top. 

Now, Burnes is a free agent and will likely be the highest paid pitcher this offseason among his free-agent class. Spending hasn’t been something that Baltimore has done, but with new ownership, that is hopefully going to change. 

Jake Rill of MLB.com recently wrote about the biggest question for the Orioles heading into the Winter Meetings. He highlighted their need to spend, but the uncertainty of how much they actually will spend. 

It's been a long time since the Orioles have the ability to spend. Former ownership, the Angelos family, didn't give general manager Mike Elias much of a blank check. So he built one of baseball's bes farm systems to compensate.

Now, with David Rubenstein leading the ownership group, he has said he is willing to spend this winter. But, until O's fans actually see it, it's logical to have questions.

"The O’s brass plans to act diligently, making smart investments for the long-term future of the franchise.," Rill wrote. W"ith that being said, the Orioles could see a significant bump in payroll for 2025. Could that include a megadeal for the likes of Corbin Burnes or someone similar? We’ll have to wait to find out.

Whether or not the Orioles are going to look to keep up with teams like the New York Yankees, Boston Red Sox, and Toronto Blue Jays in their own division could decide how competitive this team is going to be in years to come. 

Those three teams are being linked to some of the top free agents, and two of those players are from Baltimore. 

While spending over $200 million on Burnes might not be realistic for the Orioles, they are going to have to spend a lot more than they have in recent years to compete. If Baltimore doesn’t end up being aggressive in free agency, they could find themselves back at the bottom of the standings within their division despite a great young core.