Orioles rumors: Baltimore enters sweepstakes for high-profile pitching

The Orioles are checking in with all aspects of the pitching market
Sep 23, 2023; Boston, Massachusetts, USA; Chicago White Sox starting pitcher Dylan Cease (84) throws a pitch during a game against the Red Sox
Sep 23, 2023; Boston, Massachusetts, USA; Chicago White Sox starting pitcher Dylan Cease (84) throws a pitch during a game against the Red Sox / Bob DeChiara-USA TODAY Sports

With the Winter Meetings underway in Nashville, moves across the league should be kicking into full gear soon. Pitching is the clear need for the Orioles, with relief pitching a target in the wake of Félix Bautista's injury and starting pitching a target to compliment Kyle Bradish at the top of the rotation.

MLB Insider Jon Heyman on Monday night connected the Orioles to Dylan Cease, who is expected to be dealt by the Chicago White Sox this winter. The Orioles had checked in on Cease at the trade deadline, and it's not hard to see why. He's exactly the impact arm they need at the top of the rotation.

The Orioles also have baseball's best farm system, giving them the necessary prospect capital the White Sox would seek in a trade, as Cease is under team control through the end of the 2025 season.

Heyman reports that the Orioles are "trying hard" for Cease in talks with the White Sox and adds that they should have a good chance due to the plethora of prospects they have, particularly in the infield. Jordan Westburg was floated as a name that could be included in such a trade package.

Cease is exactly who the Orioles should be looking to acquire, as he fits the need they have at the top of the rotation. It would instantly deepen the group and make them more of a contender in 2024, and it fits with Mike Elias's comments about the team being prepared to move a top prospect in a trade.

The bullpen is also an area of need this winter, as upgrades in the high leverage situations are desired as Bautista is set to miss all of 2024. Heyman reports that the Orioles are considering Craig Kimbrel, Robert Stephenson, Aroldis Chapman, and Jordan Hicks, as the clear top reliever on the market in Josh Hader might be too expensive for the Orioles.

Stephenson is coming off a fantastic stretch with the Rays to end 2023, setting himself up well to make some good money this winter. While he wouldn't fill the closer role, he would give the Orioles another good setup option, paving the way for Yennier Cano to close more games. He was projected by MLB Trade Rumors to sign with the Orioles this offseason.

Hicks, like Stephenson, was also projected to sign with the Orioles. Hicks would certainly fill the void at closer, as he has experience in that department, and is coming off a strong year with both the Cardinals and Blue Jays.

If Hicks were to be brought in, Cano could be kept in a setup role, where he looked more comfortable than closer, with Danny Coulombe and Jacob Webb also acting as solid leverage options at the back end of the bullpen.

The same would be true if the Orioles were to bring in Kimbrel or Chapman. Both are established closers in the league and do it well, with Chapman at 321 career saves and Kimbrel at 417. While both are prone to their hiccups, they would instantly be upgrades in the Orioles bullpen picture and make the team that much better.

The Orioles absolutely need pitching upgrades this offseason in both the rotation and the bullpen, and this latest report by Jon Heyman is good news, as it signals that the Orioles are active in both markets and exploring both free agent and trade options. The next step is to secure the players.