Chicago Cubs: Breaking News, Rumors & Highlights

Did the Cubs Find Their Next Breakout Pitcher at Arizona Fall League?

The Chicago Cubs sent several of their prospects to the Arizona Fall League. Led by 2026 second-round pick Myles Bailey, the Cubs had an opportunity to showcase the little talent they have in their farm system.

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The Quiz of the Day

Chicago Cubs: Is Kevin Gausman worth bringing back?

Heading into the offseason, the Chicago Cubs face a looming crisis in their starting rotation. Between pending free agents Kevin Gausman, Clay Holmes,

Chicago Cubs News / ChiCitySports / October 27

Chicago Cubs: PCA’s 'baseball dad' snubs Mets to stay with Cubs

The Chicago Cubs have a lot to do this offseason. Among other things, they need to completely rebuild their starting rotation and find a way to replace their catcher and two starting corner outfielders as they head off into free agency.

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.

Milwaukee Brewers News / Yardbarker Quizzes

The 'Playoff-RBI leaders by MLB club' quiz

How many of the Live-Ball Era (since 1920) players to lead each MLB franchise in postseason RBI can you name in five minutes?

The 'NLCS MVPs' quiz

The 'Playoff HR leaders by MLB team' quiz

The 'Last 100-RBI season by team' quiz

Aaron Civale News / Bleed Cubbie Blue / October 27

A few thoughts about the Cubs and Aaron Civale

Cubs President of Baseball Operations Jed Hoyer must like Aaron Civale a lot, because he’s acquired him not once, but twice. The White Sox waived him at the end of August 2025 and the Cubs claimed him.

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 27

Cubs Fans Can Breathe a Sigh of Relief After Hitting Coach Sticks Around

According to Anthony DiComo of MLB.com, the Mets reportedly had strong interest in Cubs hitting coach John Mallee’s services, so many thought he could be on his way out.

Chicago Cubs News / Chicago Cubs on SI / October 26

2 World Series Players That Make Sense for the Cubs in Free Agency

As hard as it may be to watch, the Chicago Cubs should be locked in on the World Series. Not only should it serve as a learning opportunity as they look to return to the championship round themselves, but you never know what opportunities may arise in free agency.

Chicago Cubs News / ChiCitySports / October 26

Chicago Cubs: How the looming labor dispute might affect free agent shopping

Not only are the Chicago Cubs facing the herculean task of addressing pressing needs and filling multiple roster holes this offseason, but they’ll be trying to do that in a limited period of time.

Chicago Cubs News / ChiCitySports / October 25

Two Chicago Cubs free agent pitchers given 50-50 chance of returning in 2027

In a cartoonishly perfect world, the Chicago Cubs would open up the bank book and spend like drunken sailors to scoop up Tarik Skubal and Sonny Gray for the rotation and Adrian Morejon for the bullpen, with a bit reserved for another solid starter.

Matt Shaw News / ChiCitySports / October 25

Chicago Cubs: Two Matt Shaw Seattle Mariners trade ideas that make sense

The Chicago Cubs will be all about pitching, pitching, pitching this offseason. At least, that’s what they should be about. Although there should be concern

Chicago Cubs News / Chicago Cubs on SI / October 25

One Important Silver Lining to the Chicago Cubs' Bitter End of 2026

The 2026 season had big expectations and lofty goals. The Chicago Cubs tried to set a standard, but in the end it didn’t pan out as they had hoped. Because of the lack of postseason success, it already feels like a long offseason.

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.

Matt Shaw News / Viral Sports News / October 24

Cubs’ Matt Shaw Hit With Concerning Outlook About His Future

A Cubs Roundtable writer has identified infielder Matt Shaw as a player the Chicago Cubs could trade this offseason as the club seeks pitching help amid a crowded infield.

Chicago Cubs News / ChiCitySports / October 24

Chicago Cubs: Is it time to revisit this rumored trade target?

The Chicago Cubs are heading into the offseason with a desperate need to focus on pitching and a relative little bit of time in which to do a lot. The team’s entire end-of-season starting rotation may end up leaving via free agency.

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The 'Fewest passing-yards in a win' quiz

The 'Rushing-record by NFL team' quiz

The 'World Series Game 1 starters' quiz

The 'World Series managers' quiz

Chicago Cubs News / Chicago Cubs on SI / October 24

3 Concerning Stats That Describe the Chicago Cubs’ 2026 Downfall

The Chicago Cubs never settled into an identity in 2026. The Cubs' offense was one of the best in baseball in terms of run production but routinely struggled to produce in key moments.

MLB News / Viral Sports News / October 24

Former Chicago Cubs Shortstop Suddenly Retires at 29

Shortstop Jackson Cluff closed out his professional career in the Chicago Cubs organization and announced his immediate retirement Wednesday after eight seasons in the minors.

MLB News / Yardbarker / October 24

Brewers' Jacob Misiorowski sets World Series record in Game 1

Brewers' Jacob Misiorowski sets World Series record on first pitch of Game 1

There is no pitcher in Major League Baseball right now who throws harder and more consistently than Milwaukee Brewers ace Jacob Misiorowski.

John Smoltz Q&A: Braves legend dissects World Series matchup between Brewers, Rays

Rays vs. Brewers: Revisiting each game of the season series

The 'MLB K leaders since 1995' quiz

Tarik Skubal News / MLB on ClutchPoints / October 23

Cubs rumors: Chicago called ‘obvious fit’ for Tarik Skubal in free agency by ex-player

With the season over for 28 out of the 30 teams in MLB, rumors are already starting to swirl around pitching superstar Tarik Skubal. He will be one of the most sought-after players in free agency after finishing the campaign with the Los Angeles Dodgers.

Pete Crow-Armstrong News / On Tap Sports Net / October 23