Recent Offseason Moves Prompt MLB Insider To Add Cubs To "Winning" List

It had been a quiet offseason for many organizations, but not for the Chicago Cubs. The team not only took one of the best bats available this free agency, but also made a trade to acquire an up-and-coming arm for their starting rotation.

Before they acquired both third baseman Alex Bregman and starting pitcher Edward Cabrera, it had primarily been bargain shopping for the ballclub. However, Jed Hoyer and the Cubs brass finally decided to spend a buck, and that is why ESPN's Jeff Passan has listed them as one of six teams that are winning the offseason.

"Considering Chicago's reticence to spend in recent years -- including last winter with Bregman -- the $35 million-a-year commitment to Bregman is a welcome return to the Cubs not acting like they're run by St. Helen of the Blessed Shroud. The deal represents the largest per-year salary in Cubs history and is their biggest signing, in terms of potential impact, since adding Jon Lester andJason Heyward more than a decade ago," stated Passan.

Bregman batting against the Yankees in the AL Wild Car — Junfu Han / USA TODAY NETWORK via Imagn Images

While Chicago is battling for another 90+ win season and a bid back to the playoffs, they are also fighting to steal the crown from the Milwaukee Brewers in the NL Central. It is interesting to note that, per Passan, the Brewers are a team he thinks needs to make a move.

The Cubs are definitely the way-too-early division favorites at this point, as they addressed the key aspects the organization needed to since the season ended. 1) Replacing the production that Kyle Tucker is likely taking with him, and 2) Depth in the starting rotation.

It took some time, but both of those items were checked off in the last week.

The two big additions to the 2026 Cubs roster

A strained quad didn't keep Bregman from performing at the plate in 2025, which is why he finished the year with a 3.5 WAR and a slash line of .273/.360/.462. Despite missing more than 45 games last season as he rehabbed his injury, he still had the third-most home runs on the Red Sox roster (18) as he led the team (minimum 100 games played) in OPS (.821).

Alex Bregman comes up CLUTCH with a pinch-hit 3-run homer 😮 pic.twitter.com/H1yNreNLdx
— MLB (@MLB) July 20, 2025

There is a reason the Cubs were willing to commit to a 5-year $175 million dollar contract, and that is clear as day with the hardware in his trophy case, which includes two World Series, three All-Star appearances including MVP, a Silver Slugger, Gold Glove, and more.

MORE: Wild Nico Hoerner Trade Proposal Sees Cubs Land Future Red Sox Ace

Cabrera, on the other hand, hasn't built up near the accolades, which is why he's only costing the Cubs $4.45 million in 2026. But make no mistake, he is trending in the right direction after a breakthrough 2025 where he posted a 3.53 ERA and 150 strikeouts in 26 starts.

He has all the upside in the world, and the Cubs will have the time to help him see his potential realized.

Edward Cabrera throwing a pitch in the first inning for the Cub — Jim Rassol-Imagn Images

Spring training is rapidly approaching, and Jed Hoyer has to be feeling really good about the roster he has assembled for the 2026 season. Others are recognizing this team's potential as well, including Jeff Passan.

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