The Chicago Cubs‘ top objective of the 2026 MLB offseason is not a secret in the slightest.
The Cubs absolutely need to strengthen their pitching rotation this offseason. They have several pending unrestricted free agent starters heading into the offseason and need better pitching in general. Thus, the Cubs are going to be a fascinating team to watch in the pitching market.
The Cubs have been connected to multiple pending free agent pitchers since their playoff run ended. Yet, one who they continue to be linked to is Boston Red Sox star pitcher Sonny Gray. Now, that is not stopping, as they have once again been viewed as a favorite to land the Red Sox starter.
Chicago Cubs Continue to Be Connected to Boston Red Sox’s Sonny Gray
In a recent FanSided article, Christopher Kline named the Cubs among the favorites to land Gray this offseason.
“The Cubs need to restock and this front office has never faced more pressure to put a winning roster together,” Kline wrote. “Not only do the Brewers continue to dominate the NL Central, but Pete Crow-Armstrong won’t reach MVP heights forever. The clock is always ticking. Gray can add serious depth and viability to Chicago’s rotation as the North Siders attempt to (finally) break through.”
Given the Cubs’ pitching woes, it makes sense that Gray is continuing to be viewed as a top target for them. The Cubs are in win-now mode, and adding a star veteran pitcher like Gray would be huge for them because of it.
Gray would offer the Cubs more stability in their rotation as they look for better success in 2027. He would be an obvious fit for one of their top three spots in their rotation. This would also depend on who else the Cubs add to their roster this offseason, too.
Cubs & Gray Could Be a Perfect Match
With the Cubs looking to win the World Series next year, Gray would be a very good pitcher for them to add to their roster. The Cubs could also intrigue Gray, as they would give him the chance to play for a very good team. Thus, Gray and the Cubs could be a perfect match.
However, the Cubs are not going to be the only team interested in Gray this offseason. He is exactly the kind of star veteran pitcher that contenders love to add. Thus, the Cubs will have a lot of competition if they target him.
Yet, with Chicago’s major need for pitching help, they can bid hard to land Gray. It will be intriguing to see if they can get him from here.
Chicago Cubs Continue to Be Named Favorites to Land Red Sox Star Pitcher