Chicago Cubs: Breaking News, Rumors & Highlights

Tarik Skubal Would Be the Chicago Cubs’ Missing World Series Piece

The Chicago Cubs entered the offseason with one goal: find a way to take the next step from playoff team to legitimate World Series contender. That is why the idea of pursuing Tarik Skubal is so intriguing.

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Chicago Cubs: Thoughts on Happ, Suzuki qualifying offers

The Chicago Cubs have a lot of big decisions to make this offseason. First, they pretty much have to reconstruct an entire starting rotation. After Matthew

Chicago Cubs News / Chicago Cubs on SI / October 30

4 Under-the-Radar Free Agents the Chicago Cubs Should Target

After seeing their division rival walk away with the World Series crown, the Chicago Cubs feel even more pressure to return to the top of the NL Central.

Trent Thornton News / Bleed Cubbie Blue / October 30

A few thoughts about the Cubs and Trent Thornton

Trent Thornton is almost the definition of “fungible reliever.” After a few middling years in Toronto, Thornton wound up traded to the Mariners near the deadline in 2023.

Milwaukee Brewers News / Yardbarker Quizzes

The 'World Series MVPs' quiz

MLB has awarded the World Series MVP since 1955. How many of these players can you name in six minutes?

The 'NLCS MVPs' quiz

The 'Last MVP by MLB team 'quiz

The 'Platinum Glove winners since 2011' quiz

Chicago Cubs News / ChiCitySports / October 30

2 Chicago Cubs starting pitchers make pivotal 2027 decisions

While the Chicago Cubs made the postseason for a second-straight season, they were promptly swept in the Wild Card Series. The franchise has clear areas to improve on their roster.

Athletics News / Yardbarker

25 things we learned from the 2026 MLB season

The 2026 MLB season was full of great performances, breakout stars, and incredible feats. These are the 25 things we learned along the way.

Chicago Cubs News / Chicago Cubs on SI / October 29

The Perfect Cubs Offseason Target Just Became Available

The Chicago Cubs are going to have to do a lot of rebuilding of their pitching infrastructure in 2027 and beyond. After the disaster that was the 2026 season — whether it was injuries, trades that didn't pan out, or regression from former stars — it's now on Chicago's front office to be aggressive in pursuit of an elite rotation.

Tarik Skubal News / ChiCitySports / October 29

Chicago Cubs predicted to lose Tarik Skubal free agency sweepstakes

Entering the offseason, the Chicago Cubs’ top priority is bolstering their pitching rotation. Their crown jewel in free agency would be two-time Cy Young winner Tarik Skubal.

Pete Crow-Armstrong News / Viral Sports News / October 29

Cubs’ Pete Crow-Armstrong Reveals Next Career Step

Pete Crow-Armstrong said the mental side of baseball is the part of the game he struggles with most, and the piece he believes can take him to another level.

Chicago Cubs News / Viral Sports News / October 29

Chicago Cubs Could Lose Star Player to Hated Rival

The Chicago Cubs face a pivotal offseason decision with Ian Happ, the longest-tenured player on the roster and a four-time Gold Glove winner who has spent his entire decade-long major league career in left field at Wrigley Field.

Caleb Thielbar News / Bleed Cubbie Blue / October 29

A few thoughts about the Cubs and Caleb Thielbar

The re-signing of Caleb Thielbar by Jed Hoyer for 2026 is a perfect example of recency bias. Thielbar had a very good year for the Cubs in 2025, in some ways the best year of his career.

Athletics News / Yardbarker

25 records that were broken during the 2026 MLB season

The 2026 MLB season was historic in many ways. These 25 records were broken during the season.

Chicago Cubs News / Chicago Cubs on SI / October 29

Two Cubs Starters Decline Player Option as Future Rotation Becomes Wide Open

The Chicago Cubs have a lot of work to do this offseason, especially after watching their heated division rival win their first World Series in franchise history.

Clay Holmes News / Baseball Now / October 29

Cubs Pitcher Elects Free Agency Over $12 Million Return To Chicago

The Chicago Cubs acquired Clay Holmes at the MLB trade deadline, but now he is hitting free agency. Holmes had a $12 million player option on the three-year, $38 million deal he signed with the New York Mets before the 2025 season, and he is declining it, per ESPN's Jesse Rogers.

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The 'World Series MVPs' quiz

The '140-yard, 2-TD catch NFL games' quiz

The 'NFL's active rushing leaders' quiz

The 'Fewest passing-yards in a win' quiz

Chicago Cubs News / Yardbarker / October 29

Cubs' Boyd, Holmes decline player options, set to become free agents

Cubs' Matthew Boyd, Clay Holmes decline player options, set to become free agents

The Cubs are going to need a major overhaul of their starting rotation ahead of the 2027 season.

The 'MLB active hit leaders' quiz

Chicago Cubs News / Cubs Insider / October 29

Cubs Reportedly Reworked Hitting Coach John Mallee’s Contract to Keep Him

Shortly after word circulated that Cubs assistant hitting coach John Mallee was being considered by the Mets for a role on their coaching staff, it was reported that Mallee had withdrawn from consideration and would remain in Chicago.

Chicago Cubs News / Bleed Cubbie Blue / October 29

MLB’s 2026-27 offseason calendar: Free agents, awards, Rule 5 draft, non-tenders, arbitration, more

Congratulations to the Milwaukee Brewers on winning the 2026 World Series, the first World Series title in their 58-year franchise history. With that, baseball’s offseason commences.

Kevin Gausman News / Athlon Sports / October 29

In 2022, Kevin Gausman paid $7.65 million for a Toronto mansion; traded away, he is now asking $6.885 million — $765,000 less

Kevin Gausman’s time in Toronto has taken another step toward an ending, with the veteran pitcher reportedly listing his mansion for $6.885 million. He purchased the property for $7.65 million in March 2022, leaving the current asking price $765,000 below his original purchase price.

Adrian Morejon News / Cubs Insider / October 28

Morejon Makes Sense as Cubs May Jump Market with Multiple Pre-Lockout Deals

We’ve all been saying it for years now, and Michael Canter noted this recently as well, but the Cubs have to be aggressive this winter. But this isn’t a typical winter, as there figures to be about a month of free agency before a lockout shuts the league down until a new collective bargaining agreement is ratified.

Ian Happ News / Yardbarker / October 28

Ian Happ's consistent power makes him a compelling free agent for Blue Jays

The Toronto Blue Jays' priority this offseason revolves around bulking up on offense.

Blue Jays free agent target: Shota Imanaga

Free agent Michael Soroka would help fill Blue Jays' need for rotation depth

Mason Fluharty became the Blue Jays’ high-leverage lefty thanks to durability and strong performances

The 'Most MLB Playoff-RBIs' quiz

Chicago Cubs News / Just Baseball / October 27

Cubs Free Agents: Who Stays and Who Goes?

The Chicago Cubs have a multitude of impending free agents that will require decisions as they begin shaping their roster for 2027. Each potential departure creates a question about how to replace that player’s production, while every reunion represents a commitment of money and a roster spot.