Cubs’ Pitching Search Could Find Them Seeking Trades with Division Rivals
There will be a plethora of names mentioned as possible options for the Cubs throughout the offseason, and activity will start to pick up as soon as the World Series ends. Free agency will play a big role, of course, but trades are always the most interesting to ponder. While it may not be common, an intradivision trade could be the path Jed Hoyer takes in his search for another high-end starting pitcher.
Reports from Cincinnati have indicated that the Reds may be open to trading ace righty Hunter Greene, who still has three years remaining on the six-year, $53 million extension he signed in 2023. Though the average annual value is only $8.83 million, his actual salary will increase in each of the next three seasons. There is also a club option for $21 million that would secure the 26-year-old for the 2029 season. Injuries have held Greene back from playing a full season, but his strikeout numbers will always keep him near the top of the league when healthy.
Mark Sheldon of MLB.com appears to be speculating about Greene’s availability, but he noted the Reds’ need for more offense as a reason they could end up moving him. The Cubs have plenty of hitting prospects, although no clear pieces that could be moved for someone of Greene’s caliber. As unlikely as a big trade like this would be, it’s something to keep on the radar.
Ben Cherington and the Pittsburgh Pirates have sat near the bottom of the division for a decade, as a lack of quality ownership has prevented them from spending the money needed to field a competitive team. Their young pitching core of Paul Skenes, Jared Jones, and Bubba Chandler can offer their fans hope for the future, but that doesn’t matter when you have the worst offense in baseball.
Their lack of spending has led to several trades to clear payroll, with Mitch Keller being the next potential piece of salary that Bob Nutting can shed from his team. The 29-year-old righty was connected to the Cubs several times around the 2025 trade deadline, and some reports even said they were willing to include Owen Caissie in a potential deal. Depending on what route they take to replace Kyle Tucker‘s production, Caissie and/or another young hitter could be moved.
Keller isn’t an ace, but he has been a consistent presence in the Pirates’ rotation since 2021. The Cubs dealt with several injuries during the 2025 campaign, leaving them searching for more durable options to give their pitching staff more depth. Between his relatively pedestrian numbers and the three years left on a five-year, $77 million deal ($15.4M AAV), Keller would not command nearly the return of Greene or other ace-level arms.
One option who could be in play is Sonny Gray, the Cardinals ace who has said he may waive his no-trade clause now that new management is taking over in St. Louis. At 36 years old for the 2026 season, he’s quite a bit older than the other two mentioned here. He’s also got just one year of control at just under $25 million AAV ($35M actual) with a $30 million club option for 2027 that includes a $5 million buyout spread over five years. This one is obviously complicated because Gray has control over where he ends up, giving the Cards very little leverage.
Keller has the best chance to land in pinstripes, but we’ll find out more about what direction the Cubs choose to take once the offseason officially begins.
