Chicago Cubs: Breaking News, Rumors & Highlights

Cubs Can’t Afford To Fumble Drew Pomeranz Free Agency Chase

Veteran left-handed hurler Drew Pomeranz being traded from the Seattle Mariners to the Chicago Cubs in April 2025 didn't receive much fanfare. After all, while Pomeranz was once one of the more reliable southpaw pitchers in MLB, his last appearance in the big league was in 2021 before spending the next few seasons in the minors.

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The Quiz of the Day

Cubs in the AFL: Mesa Solar Sox Week 3 update

We are three weeks into the Arizona Fall League and since it’s a Monday off-day, it’s a good time to check in on the Mesa Solar Sox. The Solar Sox played six games this past week and won two of them and lost four of them.

MLB News / Chicago Cubs on SI / October 27

Every Report And Rumor Linking The Cubs To Free Agents And Trade Targets

The 2025 World Series hasn't even begun, yet rumors and speculation are flying about some of the biggest names that are about to hit free agency. For Chicago, the Cubs have more than a half dozen players who were with the team this season but could be on the way out if a new contract is not agreed upon.

Jed Hoyer News / Cubs Insider / October 27

Flipping Highly Coveted BBCOR Bats as Metaphor for Jed Hoyer’s Offseason Pursuits

Have you ever been totally certain a particular situation or decision was such a no-brainer that it had no option but to pan out or pay off, only to be sorely disappointed in short order?

Toronto Blue Jays 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 'World Series MVPs' quiz

The 'Four-RBI ALCS games' quiz

The '2024 MLB RBI leaders' quiz

Daniel Palencia News / Bleed Cubbie Blue / October 27

Cubs contracts: An extension proposal for Daniel Palencia

It might be too early to consider a long-term contract for Cubs closer Daniel Palencia — and yes, I’m calling him “closer” because I have no doubt he’ll be back in that role in 2026.

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.

Chicago Cubs News / Chicago Cubs on SI / October 27

Cubs Prospect Became Velocity King of Minor League Baseball in 2025

Major League prospects are chasing velocity every year. Coaching staffs are helping those prospects try to get every last bit out of each pitch. The Chicago Cubs are no different.

Pete Crow-Armstrong News / Chicago Cubs on SI / October 27

Pete Crow-Armstrong's $250 Million Contract Prediction Calls His Long-Term Future With Cubs Into Question

There's no question that the Chicago Cubs hit a home run when they traded Javier Baez (along with Trevor Williams and cash) to the New York Mets in exchange for Pete Crow-Armstrong back before the 2021 MLB trade deadline.

Chicago Cubs News / Bleed Cubbie Blue / October 27

Chicago Cubs history unpacked, October 27

Rabbit Maranville arrives in Chicago, and other stories. Happy birthday to Ralph Kiner* and other former Cubs. On Mondays, Wednesdays, and Fridays, Bleed Cubbie Blue is pleased to present a light-hearted, Cubs-centric look at baseball’s colorful past. Here’s a handy Cubs timeline, to help you follow the various narrative paths.

Chicago Cubs News / Chicago Cubs on SI / October 26

Cubs Snubbed In Insider’s Top Offseason Trade Destination Report

While the Chicago Cubs' front office has gotten flak from the fan base in the past for not being as aggressive spenders as fans think they should be, given the amount of revenue they make, Cubs President Jed Hoyer pulled the trigger on a blockbuster trade to bring Kyle Tucker to Wrigley Field in 2025.

Pete Crow-Armstrong News / MLB Trade Rumors / October 26

Extension candidate: Pete Crow-Armstrong

Few players captured more attention throughout the 2025 season than Pete Crow-Armstrong. The young center fielder seemed to launch himself into superstardom in the first half this year, with 20 doubles, 21 homers, and 25 steals through the end of June.

Kyle Tucker News / ChiCitySports / October 26

Chicago Cubs: Bold moves needed ahead of life without Kyle Tucker

The Chicago Cubs are not going to have Kyle Tucker next season. That’s just a reality fans have to keep telling themselves in order to make it sink in.

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.

Bill Buckner News / Bleed Cubbie Blue / October 26

Cubs historical sleuthing: Bill Buckner edition

Here’s a photo of the popular Cubs first baseman Bill Buckner trying to break up a play in Pittsburgh: Getty Images’ caption says: PITTSBURGH, PA – CIRCA

Click here to get Yardbarker's Quiz of the Day emailed to you!

The 'Active NFL receptions leaders' quiz

The 'ALCS MVPs' quiz

The 'World Series home run leaders' quiz

The 'Active 3-passing-TD game leaders' quiz

Shota Imanaga News / Chicago Cubs on SI / October 26

Cubs Face Crucial Decision On Shota Imanaga’s Contract — Breaking Down The Options

When the Chicago Cubs signed Shota Imanaga, the top line of the deal was four years and $53 million. But the deal is about as creative as one could imagine.

Dylan Cease News / Bleed Cubbie Blue / October 26

Chicago Cubs news and notes: Steele, Cease, Ryan Flaherty

We cover the coverage like PCA covers center field. That first WS game was fun. The Dodgers getting beat down did my heart good. Spotrac has scary Kyle Tucker figures.

Chicago Cubs News / Larry Brown Sports / October 26

Cubs expected to pursue a former Cy Young finalist in free agency

The Chicago Cubs may be about to take a big swing for their rotation. Chicago is expected to pursue San Diego Padres pitcher Dylan Cease in free agency this winter, Bruce Levine of 670 The Score reported this week.

Chicago Cubs News / Viral Sports News / October 26

Report: Cubs Interested in Reunion With Star Pitcher

The Chicago Cubs are gearing up for an aggressive offseason, with right-hander Dylan Cease emerging as a prime target to bolster their starting pitching, according to Bruce Levine of 670 The Score.

Dylan Cease News / MLB Trade Rumors / October 25

Dylan Cease, Cubs seem like match made in heaven, but that doesn't mean there will be a deal

The Cubs are viewed as a potential top suitor for Cease, and he will be pursued by the North Siders this winter.

The 25 greatest MLB players to never win an MVP

The '2023 MLB strikeout leaders' quiz

Chicago Cubs News / Chicago Cubs on SI / October 25

MLB Insider Names Intriguing Free Agent Fit For Cubs

When one thinks about where the Chicago Cubs could most stand to improve this offseason, the infield isn't the first thing that comes to mind. This is

Chicago Cubs News / ChiCitySports / October 25

Chicago Cubs tied to big-ticket free agent, per MLB insider

The Chicago Cubs finished their 2025 campaign with a tough loss after a gutsy and defiant postseason run that saw them twice stare down and get past elimination games in two separate series.

Harry Caray News / Bleed Cubbie Blue / October 25

Wrigley Field historical sleuthing: Harry Caray edition

From time to time, Cubs broadcaster Harry Caray would head to the bleachers to broadcast a game. Here’s one of those games. There’s more to the photo than you can see at the top of this post and therein lie the clues: Since we have a lot of the scoreboard visible, it’s possible to narrow this down to a specific pitch.

Chicago Cubs News / Bleed Cubbie Blue / October 25