Chicago Cubs: Breaking News, Rumors & Highlights

MLB Insider Drops Bold Owen Caissie Prediction For 2026

The Chicago Cubs have a pretty incredible player developing in the farm system for what seems like far too long: outfielder Owen Caissie. Caissie's opportunity to join the majors has been hindered due to a stacked outfield that included Ian Happ, Pete Crow-Armstrong, and Kyle Tucker.

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Dylan Cease and the Cubs seem in doubt according to MLB Insider

For Cubs fans, the idea of bringing Dylan Cease back to the organization that originally drafted him is a tantalizing prospect. The team has made it clear they’re in the market for a top-of-the-rotation arm, and Cease, despite a rocky 2025 season, fits the bill.

Chicago Cubs News / Cubs Insider / November 20

Cubs Could Trade from Thinning Farm System Rather Than Sign Big Free Agents

Budget constraints seem to be a common theme when discussing the Cubs, and that could easily become the case once again this winter. Any limits on free agency spending will spur more trade discussion, as trades can often be a more reasonable means for acquiring talent when trying to avoid big payroll increases.

Alfonso Soriano News / Bleed Cubbie Blue / November 20

Cubs walkoff heroes: Alfonso Soriano, July 27, 2009

Coming off the division title years in 2007 and 2008, hopes were high for a three-peat in 2009. But the Cubs struggled for much of the early going in ‘09.

Philadelphia Phillies News / Yardbarker Quizzes

The '50-home-run MLB seasons' quiz

How many of the players to reach the 50-home run milestone in one MLB season can you name in five minutes?

The 'Active MLB home run leaders' quiz

The 'MLB yearly runs created leaders' quiz

The 'Playoff home run leaders by MLB team' quiz

Chicago Cubs News / ChiCitySports / November 20

Chicago Cubs farm system alarms go off after harsh truths are revealed

The Chicago Cubs may soon be trying to tap a dry well when it comes to their farm system. If recent movements regarding former Cubs top prospects are any indication, there’s reason to believe that the team’s developmental system– formerly regarded by many as one of the best in baseball– might be facing some serious issues.

MLB News / Yardbarker

25 notable MLB Hall of Famers who never won a World Series

Among the countless Hall of Famers who never experienced the joy of winning a World Series, there are several notable legends who stand out. Here's our list of the 25 greatest.

Kyle Tucker News / MLB on ClutchPoints / November 20

The perfect $405 million contract Blue Jays must offer Kyle Tucker to steal him from Cubs

The Toronto Blue Jays are sitting at a critical juncture in their championship window. After pushing the Los Angeles Dodgers to seven games in the 2025 World Series and coming just two outs away from ending their World Series drought, the front office cannot afford to rest on their laurels.

Chicago Cubs News / Cubs Insider / November 20

Inevitable CBA Lockout Could Keep Cubs from Spending Big This Winter

Unless something drastic changes over the next 12 months, MLB owners and players are headed towards a lockout after the 2026 season. Whether fans realize it or not, this uncertainty surrounding the potential work stoppage will likely deter a number of teams from spending as much as they normally would this winter.

Chicago Cubs News / Bleed Cubbie Blue / November 20

Chicago Cubs news and notes — Imanaga, Tucker, Bellinger

We cover the coverage like PCA covers center field. Rumors abound but few things have materialized so far. *means autoplay on, (directions to remove for Firefox and Chrome). {$} means paywall.

Dylan Cease News / Chicago Cubs on SI / November 19

MLB Insider's Dylan Cease Take Isn't What Cubs Fans Want To Hear

Dylan Cease is the free agent pitcher whom the Chicago Cubs have been most commonly linked to this offseason. This is because the Cubs have made it known that they intend to acquire a top-tier starting pitcher.

Shota Imanaga News / MLB on ClutchPoints / November 19

Cubs rumors: Insider sees Chicago adding another starter after Shota Imanaga decision

The Chicago Cubs may not be done upgrading their rotation. Despite left-hander Shota Imanaga accepting the team’s qualifying offer this week, MLB Network insider Jon Morosi believes the Cubs will still pursue another high-end starter before the conclusion of the 2025 MLB offseason.

Chicago Cubs News / Chicago Cubs on SI / November 19

Iowa Cubs To Play Game At Iconic Field In 2026

Major League Baseball made two big announcements recently regarding a particular ballpark in Dyersville, Iowa. The site of the famous baseball-themed movie 'Field of Dreams' will play host to two games in August next year.

MLB News / Yardbarker

The 25 greatest pitching seasons from the modern MLB era

America's favorite pastime has more memorable performances than any sport. As such, figuring out which pitchers had the best seasons ever is no easy task.

Shota Imanaga News / ChiCitySports / November 19

Chicago Cubs bummed by player deciding to return in 2026: Report

On Tuesday, starting left-handed pitcher Shota Imanaga signed a one-year $22 million qualifying with the Chicago Cubs. The Cubs chose not to pick up his three-year option at the start of the offseason following a disastrous showing in the postseason, giving up an 8.10 ERA in two games pitched (6.2 innings).

Chicago Cubs News / Bleed Cubbie Blue / November 19

The Shōta Imanaga qualifying offer signing by the numbers

The stove is hot and Tuesday was the day we learned if players were going to take the qualifying offer or not. There was a bit of suspense for the Cubs

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The '2022 NFL Week 1 starting QBs' quiz

The 'NFL single-game completions leaders' quiz

The 'NFL QB rushing TD leaders' quiz

The 'NFL yearly tackles-for-loss leaders' quiz

Chicago Cubs News / Chicago Cubs on SI / November 19

Insider Reveals Why Cubs 'Might Balk' At Cody Bellinger Reunion

Given that Kyle Tucker is expected to sign with another team in free agency this offseason, the expectation is that the Chicago Cubs will try to sign another hitter who can help fill the void Tucker will leave in the middle of the Cubs' lineup.

Chicago Cubs News / Bleed Cubbie Blue / November 19

Cubs walkoff heroes: Aramis Ramirez, June 29, 2007

In 2007, the Cubs were coming off a 96-loss season. But they had a new manager, Lou Piniella, and general manager Jim Hendry had made some key acquisitions, including signing Alfonso Soriano to what was at the time the biggest contract in franchise history.

Shota Imanaga News / ChiCitySports / November 19

Chicago Cubs: Why Imanaga’s return dooms the Cubs to a mediocre winter

The Chicago Cubs are definitely okay with Shota Imanaga being back in the starting rotation for 2026. They wouldn’t have extended him the $22 million qualifying offer if they weren’t.

Chicago Cubs News / Chicago Cubs on SI / November 19

Cubs Add Trio Of Prospects To 40-Man Roster

With free agency in full swing and the Rule 5 deadline happening yesterday, the Chicago Cubs have added additional players to their roster for next season.

Chicago Cubs News / Bleed Cubbie Blue / November 19

Cubs free agent target: Tatsuya Imai

Josh already wrote about the Japanese star here last week, but I wanted to post my thoughts, especially after Shōta Imanaga accepted the qualifying offer Tuesday.

Chicago Cubs News / ChiCitySports / November 19

Chicago Cubs add MiLB Gold Glove award winner and 2 others to 40-man roster

The Chicago Cubs were busy on Tuesday, November 18. News surrounding Shota Imanaga accepting the qualifying offer stole the headlines, but the organization also added three prospects to their 40-man roster, thus protecting them from December’s Rule 5 draft.

Chicago Cubs News / MLB Trade Rumors / November 18

Cubs select top-10 prospect James Triantos, two others

The Cubs announced that they have selected infielders James Triantos and Pedro Ramírez as well as left-hander Riley Martin.

The 25 most unlikely World Series heroes

The 'Active 100-RBI MLB season' quiz

Kyle Tucker News / Total Apex Sports / November 18

Kyle Tucker Rejects Qualifying Offer From Chicago Cubs

Another day, another dollar, and another rumor mill churning out delicious “what-ifs” for the MLB offseason. The latest dish? The Los Angeles Dodgers, fresh off their second consecutive World Series win, are supposedly sniffing around top free agent Kyle Tucker.

Chicago Cubs News / Viral Sports News / November 17

Chicago Cubs Once Again Connected to Major Pitching Trade

The Chicago Cubs aren’t planning to sit on their hands this offseason. At the GM meetings in Las Vegas earlier this week, president of baseball operations Jed Hoyer told reporters, “We’re going to have an active offseason.

Chicago Cubs News / Viral Sports News / November 17

Report: Cubs Considering Major Free Agency Move for Star Pitcher

The Chicago Cubs are still reeling from a frustrating end to their 2025 Major League Baseball campaign, where they fell to the Milwaukee Brewers in the National League Division Series.

Kyle Tucker News / Larry Brown Sports / November 14

Report: Cubs expect one outcome with Kyle Tucker’s free agency

The Chicago Cubs are apparently preparing for the worst-case scenario with Kyle Tucker. Chicago “seems resigned” to their free agent outfielder Tucker going elsewhere, Jon Heyman of the New York Post reported on Friday.

Brad Keller News / MLB Trade Rumors / November 13

Brad Keller is drawing interest as a starting pitcher

Teams have shown interest in free agent right-hander Brad Keller as both a starter and reliever, reports Joel Sherman of The New York Post. It’s not clear which teams are involved, though Sherman writes that the New York Yankees have not emerged as a serious suitor to this point.