The Chicago Cubs are staring down a real situation as the team heads into an uncertain 2027, especially when it comes to their starting pitching.
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Their entire end-of-season starting rotation (Matthew Boyd, Shota Imanaga, Kevin Gausman, Clay Holmes, David Peterson) may be lost via free agency. The potential starters left behind do not inspire confidence.
Justin Steele hasn’t pitched in nearly two full seasons due to elbow surgery and then a flexor injury while rehabbing the elbow. Cade Horton will be out most—if not all—of 2027 after Tommy John surgery in April. Edward Cabrera, meanwhile, had a horrible debut season with the Cubs, suffering through injury and just general inconsistency.
With no help coming from the farm system, the Cubs will have to rely on free agent acquisitions to build up a rotation to support an offense and defense that are already top-tier.
The problem is that the 2027 free agent starting pitching market isn’t especially deep and, is usually the case, the competition for quality pitchers will be fierce.
One name immediately placed at the forefront of Cubs fans’ wish lists is Sonny Gray.
Targeting Sonny Gray
Aug 10, 2026; Toronto, Ontario, CAN; Boston Red Sox starting pitcher Sonny Gray (54) throws a pitch during the first inning against the Toronto.Blue Jays at Rogers Centre. Mandatory Credit: Nick Turchiaro-Imagn Images
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The former Cardinal, Red, Twin, Yankee, and Athletic had a career year with the Boston Red Sox in 2026 after coming over in a trade with St. Louis. On the season, he was 18-5 with a 2.72 ERA through 29 starts. He also made his third All-Star game.
Justin Binkowski of SI.com recently made the case for Chicago moving to pursue the 14-year veteran:
“The Chicago Cubs have several pitchers entering free agency this offseason, which means they should be in the market to add arms to a team that had one of the best offenses in 2026. If Gray does become a free agent, he could be one of the top candidates to be Chicago’s ace next season.
Gray has experience pitching in the National League Central with the Cincinnati Reds and the St. Louis Cardinals. A return to that division could be an option for the veteran hurler if the Cubs revamp their rotation.”
Gray would definitely be a welcomed addition to the front of a depleted Cubs rotation. Despite having lost velocity over the years, he’s still a highly effective, dogged competitor who now relies more on savvy and the ability to generate elite spin on his pitches.
Two major obstacles
Sep 23, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Sonny Gray (54) delivers a pitch against the Cleveland Guardians during the first inning at Fenway Park. Mandatory Credit: Gregory Fisher-Imagn Images
However, there are two big issues possibly standing in the way of a Cubs-Gray union.
First, Gray will soon turn 37 and he has accumulated a lot of mileage over the course of his career. He profiles as a pitcher who can be effective well past his physical prime and he’s been remarkably healthy over his major league run, but age will eventually catch up to everyone—something the Cubs will surely be taking into consideration.
Second, the righty is technically not a free agent until either he or the Red Sox turns down the $30 million pending mutual option for 2027. Gray is expected to cut ties and look for a more secure multi-year contract as a free agent. Estimates on that contract’s cost range from $63 million over two years to $75 million over three years. Both contracts would be well beyond what the Cubs generally feel comfortable paying for pitchers.
If the Cubs are serious about winning within this current window of opportunity, though, they’ll have to move beyond their comfort zone. Gray could be the ideal pickup for a pitching-needy Cubs team.
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