3 Things the Orioles Must Accomplish This Offseason

As baseball fans across the world congratulate the Milwaukee Brewers for their World Series win over the Tampa Bay Rays, an unpredictable offseason has arrived.

After the Brewers’ win, the Baltimore Orioles have climbed higher on the list of the longest World Series droughts, behind the Cleveland Guardians, San Diego Padres, Seattle Mariners and Pittsburgh Pirates.

Since 2018, every AL East team has represented the American League in the World Series (the Rays have done it twice). Meanwhile, the O’s have failed to win even one playoff game.

For the Orioles to get back to the Fall Classic, or at least make a sizable step in the right direction towards it, there are many things the team has to change. To match the competitiveness of the AL East, the Orioles front office must make even bigger swings than they have already.

However, there are three specific areas the team must address this offseason if they want any chance of playing deep into October in 2027.

No. 1: Bring Back Trevor Rogers

While many of the Orioles may not have had the seasons they were projected to have, it is important ot acknowledge the performances that kept the team in the playoff hunt deep into September.

While Pete Alonso’s was undoubtedly the O’s best player this season, kudos are in order for Trevor Rogers for being a rock in a rocky rotation.

Coming off a stellar 2025, questions swirled through the entire offseason about whether the southpaw could replicate that performance. After he posted a 1.81 ERA and 0.903 WHIP in just 18 starts, the Orioles would have accepted even a fraction of that level of production.

Rogers followed up that fantastic 2025 season with a steady campaign. In some ways, his 2026 season was an improvement over his previous season’s work.

Let’s start with the fact that 2026 was Rogers’ healthiest season of his career, making 30 starts and pitching 169.2 innings, both career highs. After he faced injury trouble at the end of his time with the Miami Marlins and the first part of his stint with the O’s, watching Rogers take the mound every five days was a welcome sight.

Rogers nearly matched his K/9 from 2025, 8.5 in 2025 to 8.3 in 2026, while also managing to lower his BB/9 from 2.4 in 2025 to 2.1 in 2026.

Also, don’t let the 4.05 ERA fool you. If it were not for subpar defense from the team, Rogers’ ERA would have been much closer to his 3.45 FIP. The 28-year-old had a very under-the-radar season, especially in a contract year.

Now, Rogers is an unrestricted free agent. The southpaw is hitting the market following two solid years that will have top teams looking to acquire his talent.

Despite signing fellow starting pitchers Shane Baz and Kyle Bradish to extensions earlier this year, the Orioles were unable to come to terms on a new deal with Rogers to keep him in the Charm City.

Instead, the Orioles extended Rogers the qualifying offer, a one-year, $23.15 million deal that, if he rejects, will give the team a compensatory draft pick. With Rogers’ recent success, he is unlikely to accept the offer. If he plays his cards right, he could be earning a higher AAV on a multi-year deal.

If you’re the Orioles’ new GM Jared Banner, how can you try to build on the team by letting your best starter over the past two years leave in free agency?

Bringing back Rogers not only locks in the top three starters in the rotation for years to come, but it also provides stability in the clubhouse. Veteran experience that is familiar with the organization will be necessary to turn things around.

Orioles ownership and their front office have expressed that more moves have to be made to fix things. After taking a big swing with Alonso’s signing, it’s time to take another one with Rogers.

No. 2: Address the Top of the Lineup

No matter what kind of moves the team makes to strengthen the rotation, big changes have to be made to the lineup as well. A strong lineup on paper wildly underperformed this past season, creating doubt as to whether the team has the right players in place to challenge for a World Series title.

Of the players who appeared in at least 100 games for the O’s, a major gap exists between Pete Alonso and the rest of the lineup. While Taylor Ward tops the list with a .383 on-base percentage, his trade to the Mariners at the trade deadline disqualifies him from this comparison.

After Alonso’s .363 on-base percentage, the next best qualifying player was Colton Cowser, who recorded a .317 on-base mark. Gunnar Henderson was hot on his tail with a .309, followed by .307 for Dylan Beavers and .297 for Coby Mayo to round out the top five.

Now, compare that to the World Series champion Brewers. Of players who appeared in at least 100 games, their top-five on-base percentages were .390, .389, .366, .354, and .351. That’s a 54-point difference between Milwaukee’s fifth-best and Baltimore’s fifth-best.

For one reason or another, the Orioles offense failed to get on base at a high enough rate. The players who were drafted to fill key spots in the lineup have failed to deliver so far, leaving the team in a pickle when it comes to relying on runs outside of the long ball.

After Jackson Holliday was selected first overall in the draft back in 2022, it was easy to look to the future and picture him, Adley Rutschman, and Jordan Westburg getting on base at the top of the lineup while bats like Henderson, Cowser, and Ryan Mountcastle drove them in with their power.

In 2026, however, that vision has become nothing but a fantasy. Injuries, trades, and a lack of development have proved that idea worthless.

The simplest way the team can fix this is for the players still on the roster to make improvements in the offseason. When healthy (and on paper), the talent of Holliday, Westburg, and Henderson should be a strong enough top three to challenge opposing pitchers. If those guys can find a way to produce more consistently, bats like Alonso, Mayo, and Samuel Basallo will have more opportunities to drive in runs.

If the front office does not believe that the current players can get to that level of production next season, moves can be made to bring in outside help. Adding an outfielder like Steven Kwan or Randy Arozarena and/or an infielder like Luis Arraez could be offseason moves that help get the offensive motor firing on all cylinders in 2027.

No. 3: Solidify the Back End of the Bullpen

The front office’s work this offseason won’t be complete until more talent is added to the back of the Orioles bullpen.

For a group that faced numerous questions heading into the season, arms like Anthony Nunez, Yennier Cano, and Ryan Helsley (when healthy) showed promise that the makings of a good bullpen were in sight.

However, it was obvious that there were issues in the back end of the bullpen. With Helsley missing significant time due to injury and Félix Bautista not returning from injury until the end of September, the O’s frequently did not have the ability to close out games.

The Orioles will not have to worry about filing Helsley’s spot on the roster after he opted into his player option for the 2027 season. Bautista is also on track to have a healthy offseason after missing time each of the past four seasons due to injury.

When it comes to making additions, the front office should look for another high-leverage righty as well as two high-leverage lefties. While that may seem like a lot, having too many mouths to feed is a good problem to have, especially as a team competing in the AL East.

For southpaws, there are plenty of arms on the market that the Orioles could target. Sean Newcomb, Steve Okert, and Alex Vesia are all additions that would drastically boost the bullpen’s performance. The O’s should also keep an eye on San Diego, where All-Star Adrian Morejon is making his decision after being extended a qualifying offer.

The right-hander market is a little thinner unless the team wants to acquire another closer-like arm in Raisel Iglesias or David Bednar, if he rejects the qualifying offer. Bryan Abreu, Emilio Pagán, and former Orioles Shawn Armstrong and Mark Leiter Jr. are all possibilities the O’s could consider.

Putting It All Together

With so much uncertainty surrounding what the MLB season is going to look like next year, it is impossible to determine how teams will handle the winter months.

For the Orioles, the 2027 season will be a very telling campaign for what direction this team is going to take. Another lackluster season could ignite big changes in the team, while a rebound season could build back the positive momentum the team has lost over the past two years.

Regardless of the moves the front office makes this winter, the common denominator in the O’s finding success already resides in the Charm City: their young players.

Without Henderson, Holliday, Westburg, Cowser, and Basallo playing to the levels they were once expected to, it will not matter if Rogers returns or if the bullpen is shored up.

The keys to the Orioles’ future lie in the hands of the former top prospects that Orioles fans endured years of miserable baseball to acquire. If the core does not make the necessary steps in 2027, it may be the last time we see this core take the field in Baltimore.