Cubs could turn Jared Banner hire into a surprising Orioles trade opportunity

The Chicago Cubs' first big loss of the offseason has already occurred, and it's not Seiya Suzuki, Clay Holmes, or any of the other key impending free agents who they're at risk of seeing sign with other teams this winter. Instead, this loss came in the front office, as former Assistant GM Jared Banner was tapped by the Orioles to become their new GM under president of baseball operations Mike Elias.

Banner joined the Cubs organization following the shortened 2020 from the Mets organization, and his time with Chicago is perhaps best defined by being credited as the most vocal voice in the room pushing for the team to acquire then-prospect Pete Crow-Armstrong in the Javier Baez deal at the 2021 trade deadline. That's a decision that ultimately brought the Cubs a superstar and likely NL MVP award winner, and the front office will now be without Banner's insight.

The loss of Banner from the front office is surely a heavy blow, but there is an upside here. The Orioles organization now becomes the latest organization (joining the Tigers and Red Sox, among others) that has strong ties to Cubs president of baseball operations Jed Hoyer in a high-level front office role. Those are the sorts of relationships that can facilitate a trade in an insular industry like baseball, leaving the Cubs in prime position to take advantage of Banner's new role.

Jared Banner's Orioles have two interesting buy-low candidates for the 2027 Cubs

Coming off a 2026 season where they missed the playoffs and finished below .500 for the second season in a row, the Orioles are looking like a team in need of change. They already jump-started their farm system with new talent by trading Adley Rutschman to the Red Sox for a haul, but there's a lot more work that needs to be done if Baltimore is going to compete next year, making the most of a core highlighted by Gunnar Henderson, Kyle Bradish, and Pete Alonso.

The biggest problem Baltimore has headed into this offseason is that they have a lot of holes to fill without many resources to fill them. RosterResource at FangGraphs highlights the club's payroll situation, pointing out that the Orioles spent nearly $163M on payroll this past year and have just over $100M on the books already for next year. That figure doesn't fully account for options and arbitration salaries, which could push the team's payroll closer to $130M before they add anything.

That's where the Cubs, who have a lot of money coming off their books and plenty of needs to fill, could come in to help out. The Orioles have two veterans on their roster that they surely would prefer not to pay the fully salaries of headed into next year, but could represent interesting rebound candidates for the Cubs if acquired in the right deal: outfielder Tyler O'Neill and closer Ryan Helsley.

O'Neill is set to make $16.5M in 2027. He's struggled in Baltimore with a wRC+ of just 93 across 139 games with the team over the past two years, but his .331 xwOBA with the Orioles is much closer to his career .338 figure than his actual production would suggest. At his best, O'Neill is a 30-homer slugger who takes his walks despite a high strikeout rate. That's a profile the Cubs could use from the right side to help balance the more contact-oriented approaches of Nico Hoerner and Alex Bregman.

O'Neill would slide into an outfield and DH mix that's presently occupied only by Matt Shaw and Pedro Ramirez, the latter of whom has barely played any outfield in his career. Adding that sort of veteran presence to the mix will be necessary. While another AL outfield bat is getting more attention as a Cubs target lately, the free agent market lacks much right-handed pop outside of Suzuki and Randy Arozarena. The Cubs are unlikely to spend in that tier, so perhaps O'Neill could be a budget option.

Helsley would be an even better fit for the Cubs' needs than O'Neill. The hard-throwing closer had an injury-plagued year with the Orioles and missed most of the year due to elbow inflammation, but he could be the exact piece the Cubs need for their bullpen next year if he's healthy enough to play. In 12 appearances before he went on the injured list for the first time, Helsley pitched to a 2.53 ERA and 2.26 FIP while collecting seven saves and posting a 32.3% strikeout rate.

That's the exact sort of elite bullpen production the Cubs sorely needed this year, and the team was even connected to Helsley in free agency last offseason. Now that Helsley is heading into 2027 with a one-year, $14M club option he seems certain to pick up, perhaps the time is right for Hoyer's front office to strike on the high-velocity, proven closer the Cubs have needed for so long.

If the Cubs agreed to take on most of the money from O'Neill and Helsley, acquiring the pair should require only a modest return given those bloated salaries and the uncertainty surrounding both players. If the Cubs agreed to take on $18M of the $30.5M combined the pair are owed next year, could a pair of mid-level prospects close to MLB get it done? Losing, for example, B.J. Murray and Grant Kipp would be well worth the risk for the Cubs and give the Orioles some immediate MLB help.

That's just one hypothetical structure, and the sides could play with the money exchanging hands in order to sweeten the return for the Orioles. Perhaps there's even a world where the Cubs swap their own injured relief addition from last offseason over to Baltimore, Phil Maton, in order to balance out the financials of the deal while providing the Orioles with something more tangible than they'd get from offering the Cubs cash considerations outright.

The possibilities are nearly endless but, regardless of what structure a hypothetical deal ultimately takes, the Cubs could certainly make use of both O'Neill and Helsley. If the Orioles are itching to move on from one or both of those players this offseason, Banner would be wise to give his old boss a call and see if there's a deal to be made.

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