Chicago Cubs: Breaking News, Rumors & Highlights

Chicago Cubs 2027 Free Agency Moves to Make to Become True Contenders

The Chicago Cubs have plenty of questions to answer after another disappointing postseason ending, and the decisions made over the next few months could determine how far this team goes in 2027.

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The Cubs could be forced to reveal some proprietary financial information

Well now, that’s a provocative headline. Here’s the story. Wrigley View Rooftop was one of a handful of rooftop clubs that were not bought out by the Ricketts family over the last few years (those that were, you can tell by the WRIGLEYROOFTOPS.COM signs on the buildings).

Chicago Cubs News / Chicago Cubs on SI / October 21

Cubs Make Decision on Pitching Coaches After Chaotic 2026

While the Chicago Cubs will inevitably make some changes to their bullpen and starting rotation, the coaching staff will remain the same. According to a report by The Athletic's Patrick Mooney and Sahadev Sharma, the full expectation is that the Cubs will keep pitching coach Tommy Hottovy and assistant pitching coach Casey Jacobson.

Chicago Cubs News / MLB Trade Rumors / October 21

Cubs To Make International Scouting Hire

The Cubs are expected to bring in longtime Rays international scouting director Steve Miller, as first reported by Francys Romero of BeisbolFR. Miller will serve as vice president of Chicago’s international scouting department.

Tampa Bay Rays News / Yardbarker Quizzes

The 'ALCS MVPs' quiz

MLB has been awarding the American League Championship Series MVP Award since the 1980 season. How many of the winners in that time can you name in six minutes?

The '2026 MLB Opening Day starters' quiz

The 'MLB K-leaders by league' quiz

The 'MLB K leaders since 1995' quiz

Chicago Cubs News / ChiCitySports / October 21

Report: Chicago Cubs had major deadline trade nixed at last minute

The Chicago Cubs were given credit for doing the best they could at this year’s trade deadline to bolster a banged-up, depleted pitching staff. In total, they acquired Kevin Gausman from the Blue Jays, Clay Holmes from the Mets (along with outfielder Tyrone Taylor), Braxton Garrett from the Marlins, and Ryan Zeferjahn from the Angels.

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 / Bleed Cubbie Blue / October 21

A few thoughts about the Cubs and Shōta Imanaga

It occurred to me recently that while I’d done an article in this series about most of the Cubs who will be free agents or who have options, I hadn’t done one on Shōta Imanaga.

Steven Kwan News / TWSN / October 20

The Chicago Cubs Need to Acquire Steven Kwan From the Cleveland Guardians

The more you think about it, the more a Steven Kwan trade makes sense for the Chicago Cubs. At first glance, Kwan is not the type of player who grabs headlines.

Chicago Cubs News / On Tap Sports Net / October 20

Report: Cubs Expected to Keep Pitching Coaches Tommy Hottovy, Casey Jacobson for 2027

The Cubs aren’t blowing up the pitching side of Craig Counsell’s staff. Pitching coach Tommy Hottovy and assistant pitching coach Casey Jacobson are expected to be retained for 2027, The Athletic’s Patrick Mooney and Sahadev Sharma reported Tuesday.

Chicago Cubs News / Chicago Cubs on SI / October 20

Will the Cubs Make Another Push for Reid Detmers This Offseason?

The Chicago Cubs desperately need starting pitchers. You know it. I know it. Jed Hoyer knows it. Yes, the organization did attempt to address this clear area of weakness at the MLB trade deadline.

Chicago Cubs News / ChiCitySports / October 20

Chicago Cubs under-the-radar trade idea could pay off big-time

The Chicago Cubs’ primary focus this offseason is pitching. That’s certainly no surprise as the team faces an unprecedented rebuilding task this winter/spring.

Tarik Skubal News / ChiCitySports / October 20

Do the Chicago Cubs have an inside track to Tarik Skubal?

The Chicago Cubs have a good news-bad news offseason awaiting them. The bad news is that they have a lot to do in a short period of time, especially when staring down the likelihood of a prolonged labor dispute this winter/spring.

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 20

3 Young Cubs Players Who Could Land in a Trade This Offseason

Let's be honest, the Chicago Cubs don't have a ton of moving parts to include in trades this offseason. Most of their core is locked up for the next few years, aside from a couple of potential openings in the outfield.

Chicago Cubs News / MLB Trade Rumors / October 20

Cubs To Retain Both Pitching Coaches

The Cubs had to navigate a litany of injuries in the rotation and bullpen this season. A handful of trade deadline acquisitions added an extra wrinkle to managing the staff.

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The 'ALCS MVPs' quiz

The 'Most NBA games played' quiz

The 'Last 30-TD season by NFL team' quiz

The 'Most WNBA double-doubles' quiz

Seiya Suzuki News / Viral Sports News / October 19

Chicago Cubs Land New $90 Million Seiya Suzuki Update

The Chicago Cubs enter the offseason weighing the future of right fielder Seiya Suzuki, a consistent offensive contributor whose next contract could reshape the outfield for 2027 and beyond.

Chicago Cubs News / ChiCitySports / October 19

Chicago Cubs steal Rays executive after losing one to Orioles

On Monday, it was announced that former Chicago Cubs assistant general manager Jared Banner was leaving the organization to become the Baltimore Orioles next GM.

Chicago Cubs News / Cubs Insider / October 19

Cubs Hire Steve Miller as New VP of International Scouting

Some people call him the space cowboy; some call him the gangster of love. Some people call him Maurice, ’cause he speaks of the pompatus of love. But now they call Steve Miller the Cubs’ new VP of international scouting after serving in a similar role for the Rays since 2019.

Chicago Cubs News / Bleed Cubbie Blue / October 19

AFL Mesa Solar Sox Update: Kade Snell breaks out

With the start of another week, it’s time for an update on the Cubs’ Boys of Autumn playing in the Arizona Fall League. If you haven’t been following along or if you just need a refresher on what is going on in Arizona, check out the introduction and the recap of the first full week.

Cade Horton News / ChiCitySports / October 19

Chicago Cubs: This Cade Horton estimated return date is a real bummer

When Chicago Cubs’ emerging ace Cade Horton was pulled from just his second start of the 2026 campaign and then designated for Tommy John surgery shortly thereafter, it was a total buzzkill.

MLB News / Baseball Now / October 19

Cubs Should Target Rays Pitcher In Free Agency This Offseason

The Chicago Cubs have one of the best offenses in baseball, but need to fix the starting rotation this offseason. The Cubs have Edward Cabrera under contract for next season, and Matthew Boyd has a mutual option.

Chicago Cubs News / Viral Sports News / October 18

Chicago Cubs Projected to Make Questionable $84 Million Move

The Chicago Cubs enter the offseason with a clear mandate to rebuild their starting rotation. Injuries and inconsistency plagued the staff throughout 2026, leaving the club thin behind a handful of reliable arms and exposed in the postseason.

Alex Bregman News / MLB on ClutchPoints / October 15

Cubs star Alex Bregman is 1 of many hitters to stink in playoffs, and he knows exactly why

Chicago Cubs third baseman Alex Bregman endured a disappointing 2026 postseason as offensive struggles continued to plague hitters across Major League Baseball.

Chicago Cubs News / On Tap Sports Net / October 15

Five Cubs Named Gold Glove Finalists

The Chicago Cubs continue to build a reputation as one of baseball’s best defensive teams, and Wednesday’s Gold Glove Award finalist announcement gives North Side fans another reason to be proud.

Dansby Swanson News / Athlon Sports / October 14

Cubs Make Dansby Swanson Announcement After 11th MLB Season

The Chicago Cubs season came to a disappointing end in the National League wild card round. The Cubs looked like one of MLB’s best teams at times while also looking like one of the worst at others.

Chicago Cubs News / Larry Brown Sports / October 2

Cubs are not expected to bring back one player next season

The Chicago Cubs are officially out of the playoffs, and that could also mean that one notable player has played in his final game for them. Chicago is not expected to get into a bidding war for their veteran outfielder Seiya Suzuki, Patrick Mooney and Sahadev Sharma of The Athletic reported Thursday.