Cubs Earn An 'A' For Their Offseason

The Chicago Cubs were very active this offseason. A couple of months after making the National League Divisional Series, the front office knew they had to make this team better this winter.

So, the Cubs went out and improved their rotation, revamped their bullpen, and found a solid replacement for Kyle Tucker atop their lineup. Those were the three biggest needs for this team heading into the offseason. 

And the North Siders addressed all three needs.

Following the rotation’s struggles in last year’s postseason, Chicago had to add a top-of-the-line starting pitcher in the offseason. Despite missing out on free agent pitchers like Dylan Cease and Tatsuya Imai, the Cubs pivoted to the trade market. 

In the trade market, they eventually found their frontline starting pitcher. The Cubs and Miami Marlins reached a deal that sent pitcher Edward Cabrera to the Windy City in exchange for top prospect Owen Caissie and two other prospects. 

The addition of Cabrera now gives the Cubs six strong rotation arms once everyone is healthy. Cabrera joins a group of Shota Imanaga, Matthew Boyd, Cade Horton, Jameson Taillon, and Justin Steele. 

The bullpen will look a bit different this season, especially with Brad Keller, Drew Pomeranz, and Andrew Kittredge all gone. But the Cubs replaced those quality relievers with high-upside arms. 

The team signed Phil Maton, Hoby Milner, Jacob Webb, and Hunter Harvey in free agency. Maton is coming off his best season. Milner has been a workhorse out of the bullpen in each of the past four years. Webb has finished with a sub-3.05 ERA in back-to-back seasons, and Harvey has shown his potential on the mound when healthy. 

Those four new additions, along with Caleb Thielbar, Daniel Palenica, and Colin Rea, make this a solid bullpen entering the 2026 season. 

Then, the Cubs made their biggest move of the offseason in mid-January by signing Alex Bregman to a five-year, $175 million contract. That marked the third biggest contract signed in the team’s history. 

Bregman brings leadership and playoff experience to that Cubs clubhouse. Most importantly, he firmly replaces Tucker at the top of Chicago’s lineup. The veteran has finished with at least a 3.5 WAR in four consecutive seasons. 

There’s no doubt that the Cubs made a lot of moves this winter. The highlight of their offseason was trading for Cabrera and signing Bregman to a massive contract. 

Given all those moves made by the Cubs, Jim Bowden of The Athletic was a big fan of their offseason. Bowden gave the North Siders an ‘A’ offseason grade. Only the Los Angeles Dodgers (A+) had a better offseason grade. 

So, it appears to have been a successful offseason for the Cubs.