The Cubs already took a hit this offseason, but it wasn’t on the player side. It came in the front office, where former assistant GM Jared Banner has been hired by the Orioles to serve as their new GM under president of baseball operations Mike Elias.
For Chicago, that’s a meaningful loss. Banner arrived from the Mets organization after the shortened 2020 season, and his most notable stamp on the Cubs may be the push to land Pete Crow-Armstrong in the Javier Baez deal at the 2021 trade deadline. That move helped bring the Cubs a player who has since grown into a superstar and likely NL MVP award winner.
But Banner’s move to Baltimore might also open a door for the Cubs.
The Orioles now join a growing list of clubs with direct links to Cubs president of baseball operations Jed Hoyer in a high-level baseball ops role. In a business where relationships matter, that kind of connection can make trade talks a lot more natural. If Baltimore decides to shake up its roster, the Cubs could be positioned to take advantage.
And Baltimore looks like a team that may need to do some shaking. The Orioles missed the playoffs in 2026 and finished under .500 for the second straight season. They already moved Adley Rutschman to the Red Sox for a haul, but there’s still plenty of work to do if they want to build around a core led by Gunnar Henderson, Kyle Bradish, and Pete Alonso.
The issue is money. RosterResource at FangGraphs notes that Baltimore spent nearly $163M on payroll last year and already has a little over $100M committed for next season. That number doesn’t yet include options and arbitration salaries, which could push the club near $130M before it adds another player.
That’s where Chicago could enter the picture. The Cubs have money coming off the books and clear needs to address, while Baltimore has veterans it may not want to carry at full freight into 2027. Two names stand out: Tyler O'Neill and Ryan Helsley.
O'Neill is owed $16.5M in 2027, and his Baltimore stint has not matched the kind of ceiling that made him attractive in the first place. He posted a 93 wRC+ across 139 games with the Orioles over the last two years.
Still, his .331 xwOBA in Baltimore is much closer to his career .338 mark than the surface results show. At his best, O'Neill is a 30-homer bat who can draw walks despite the strikeouts, and that right-handed power would give the Cubs something they need alongside the more contact-driven games of Nico Hoerner and Alex Bregman.
He’d also fit into an outfield and DH mix that, right now, is light on certainty. Matt Shaw and Pedro Ramirez are the only names mentioned in that group, and Ramirez has barely played the outfield in his career. The Cubs need veteran help there, and with the free-agent market thin on right-handed power outside of Suzuki and Randy Arozarena, O'Neill could emerge as a more affordable target.
Helsley might make even more sense. The Orioles closer lost most of the season to elbow inflammation, but when he was on the mound, he looked like the kind of arm that can change a bullpen. In 12 appearances before landing on the injured list for the first time, he put up a 2.53 ERA, a 2.26 FIP, seven saves, and a 32.3% strikeout rate.
That’s the sort of production the Cubs badly lacked this season. They were tied to Helsley in free agency last offseason, and now he heads into 2027 with a one-year, $14M club option that he seems certain to pick up. If Chicago wants a proven, high-velocity closer, this is the kind of opportunity worth circling.
Because of the salaries involved and the questions around both players, the price for a deal like this might not be steep if the Cubs are willing to absorb most of the money. If Chicago took on $18M of the $30.5M combined O'Neill and Helsley are owed next year, a package built around mid-level prospects close to the majors could be enough.
Names like B.J. Murray and Grant Kipp could be part of that kind of conversation.
There are other ways to structure it, too. The Cubs could shuffle money in different directions to make the deal work better for Baltimore, and even Phil Maton could be part of the equation if Chicago wanted to balance the finances while giving the Orioles a more immediate piece than cash considerations.
However it’s built, the logic is simple: the Cubs could use both players, and the Orioles may be interested in moving on. With Banner now in Baltimore and Hoyer on the other end of that relationship, this is the kind of connection that can turn a front-office loss into a trade advantage.
In Other News...
Cubs Fans Can Imagine How Brutal This Realignment Would Be
A hypothetical MLB realignment making the rounds online would put the Cubs in a place their fans would find hard to stomach: the American League East, alongside the Yankees and Red Sox. The idea came from blogger Kody Duncan as part of a speculative argument about fairness if the next collective bargaining agreement does not include a salary cap or floor, and it is not an official league plan.
Even so, it is the sort of exercise that gets attention because it forces a teams supporters to picture just how different life could look overnight. For the Cubs, the appeal of a familiar National League landscape would give way to a far rougher weekly grind, and the concept alone is enough to make people wonder how much of the clubs current competitive edge would survive such a shakeup. [Read more 🡒]
Cubs 2027 Outlook Suddenly Hinges On Three Defining 2026 Performances
The Cubs long-range picture is already starting to take shape around a few 2026 seasons that could echo well beyond the year itself. Pete Crow-Armstrongs 40-40 breakout and contract extension gave the lineup a cornerstone, while Alex Bregmans strong second half and Seiya Suzukis steady production helped reinforce an offense that looked more complete by seasons end.
The bigger question now is how those gains line up with the pitching side of the roster, where Ben Brown and Cade Horton both carry injury concerns that cloud the 2027 outlook. For a team trying to build a sustainable core, the difference between a healthy, dependable rotation and another round of uncertainty could end up shaping how aggressive the Cubs can be around the rest of that young offensive foundation. [Read more 🡒]
Cubs Get Another Shot At A Starter They Couldn't Land Before
Michael King is back on the market, and for the Cubs that means another chance to chase a starter they were unable to land before. After declining his player option with the Padres, King will become a free agent coming off a season in which he made 32 starts, posted a 3.21 ERA and struck out 21% of the hitters he faced, a profile that should draw plenty of attention from clubs looking to deepen the top of their rotation.
Chicago is viewed as a potential fit, and this time the Cubs will get a cleaner shot at a pitcher who checks a lot of boxes for a team trying to keep pace in a crowded National League race. Analysts are projecting his next deal could land around four years and $118 million, which would put the conversation squarely in the range of how aggressive the Cubs want to be this winter. [Read more 🡒]