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Jacob Webb News / Bleed Cubbie Blue / October 20
A few thoughts about the Cubs and Jacob Webb 
The Cubs signed right-hander Jacob Webb to a one-year deal worth $1.5 million last December. The contract came with a team option for 2027 for $2.5 million.
Chicago Cubs News / Bleed Cubbie Blue / October 20
Chicago Cubs news — Busch, Rolison, Horton
Today’s Reflections Good morning, everyone. Monday night withstanding, as Cleveland threw a hodge-podge of relievers at the Devil Rays, just think if the Cleveland pitching and Cubs defense got together.
Chicago Cubs 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.
The 'NLCS MVPs' quiz
MLB has been awarding the National League Championship Series MVP Award since the 1977 season. How many of the winners can you name in six minutes?
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.
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 / 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.
Chicago Cubs News / ChiCitySports / October 19
Chicago Cubs: One bold trade to deal with looming outfield crisis
The Chicago Cubs are in “win now” mode with a definite window of opportunity when it comes to capturing another championship as Pete Crow-Armstrong enters his prime and veterans like Alex Bregman and Dansby Swanson drift off into their post-prime.
MLB News / Chicago Cubs on SI / October 19
Cubs Lose High-Ranking Exec to Orioles, Steal Another From the Rays
The Chicago Cubs will see one of their top executives depart the franchise this offseason. According to ESPN's Jeff Passan, Jared Banner is joining the Baltimore Orioles as the franchise's next general manager.
MLB News / ChiCitySports / October 19
Baltimore Orioles poach Chicago Cubs exec before hot stove warms
Eliminated from the playoffs, the Chicago Cubs are beginning to plot out what they want their offseason to look like. However, the franchise will have to do so without one crucial voice in the room.
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.
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 / ChiCitySports / October 18
Chicago Cubs: 4 offseason steps to a 2027 World Series
Okay, the title of this column is a bit clickbait-y. The Chicago Cubs have a lot to do this offseason if they want to even make a serious playoff run. A cause for optimism, though, is that while a lot needs to be done, their needs are very well-defined and simple to target.
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.
Chicago Cubs News / ChiCitySports / October 17
Chicago Cubs: Who’s left to trade for those gaping 2027 roster holes?
The Chicago Cubs are facing a gargantuan task this offseason. First, they’re going to have to rebuild their entire starting rotation. The whole end-of-season rotation (Matthew Boyd, Shota Imanaga, Kevin Gausman, Clay Holmes, David Peterson) could be gone via free agency.
Chicago Cubs News / Viral Sports News / October 17
Cubs Urged to Pursue Blockbuster $149.5 Million Offseason Move
The Chicago Cubs must prioritize starting pitching this offseason after their rotation is projected to lose four key pieces to free agency, according to an analysis published by Cubs Roundtable.
Chicago Cubs News / ChiCitySports / October 17
Pete Crow-Armstrong credits Alex Bregman advice for monster 2026 season
The Chicago Cubs may have had a disappointingly short run in the playoffs this season, but there was no disappointment at all when it came to the corner turned by their franchise asset Pete Crow-Armstrong.
Chicago Cubs News / Chicago Cubs on SI / October 16
What Does a Successful Cubs Offseason Actually Look Like?
Speculation is already surrounding the Chicago Cubs' offseason. With plenty of roster holes to fill, the team needs to find ways to improve and contend for a World Series title.
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.
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 / Just Baseball / October 9
Where the Cubs Stand After an Abrupt End to the 2026 Season
The 2026 Chicago Cubs season ended on a pretty low note, considering how the regular season went. They were in a commanding position to secure home-field advantage for the Wild Card round before losing it to the Padres in the final days of the regular season.
Craig Counsell News / TWSN / October 8
Another October Collapse Raises Tough Questions About Craig Counsell
When the Chicago Cubs hired Craig Counsell before the 2024 season, the move was framed as a franchise altering moment. Counsell arrived with a reputation as one of baseball’s sharpest managers, someone who had consistently elevated Milwaukee’s roster for nearly a decade.
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.
Kevin Gausman News / Yardbarker / October 2
Why Kevin Gausman, Blue Jays reunion is looking more realistic this offseason
With the Chicago Cubs' early exit from the postseason and Kevin Gausman being a pending free agent this offseason, a reunion with the veteran is looking more realistic for the Toronto Blue Jays.
Chicago Cubs News / Yardbarker / October 1
Pete Crow-Armstrong shoulders blame after Cubs' wild-card loss
The Chicago Cubs season has come to an end with two losses to the San Diego Padres in the Wild Card Series at Petco Park.
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This site is for entertainment purposes only.
There is no gambling offered on this site.
Gambling Problem? Call 1-800-Gambler.