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Dontrelle Willis News / Bleed Cubbie Blue / November 10
Chicago Cubs history unpacked, November 10 — Boudreau, Vaughn, Sutcliffe, Willis 
Hippo Vaughn re-ups and other stories. Happy birthday, Micah Bowie* and other former Cubs! On Mondays, Wednesdays, and Fridays, Bleed Cubbie Blue is pleased to present a 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 / The Forkball / November 10
The Fallout and Reparation of the Chicago Cubs
In a season brimming with hope from the onset, the soaring Chicago Cubs were eventually sent tumbling back down to earth after losing to the Milwaukee Brewers in the NLDS.
Chicago Cubs News / ChiCitySports / November 9
Assessing the Cubs’ free agent relievers most likely to return in 2026
The Chicago Cubs enter the offseason with several key members of their bullpen hitting free agency. Left-handed pitchers Taylor Rogers, Caleb Thielbar, and Drew Pomeranz are all free agents, along with right-handers Brad Keller, Ryan Brasier, Michael Soroka, and Aaron Civale.
The 'World Series MVPs' quiz
MLB has awarded the World Series MVP since 1955. How many of these players can you name in six minutes?
Taylor Rogers News / Chicago Cubs on SI / November 9
Why Cubs Should Consider Taylor Rogers Free Agency Reunion
On July 30, 2025, the Cincinnati Reds traded left-handed reliever Taylor Rogers to the Pittsburgh Pirates. One day later, Rogers was traded to the Chicago Cubs for outfield prospect Ivan Brethowr.
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.
MLB News / Bleed Cubbie Blue / November 9
A report from the Arizona Fall League Home Run Derby
As the first snows of late fall hit the streets of Chicago there is still baseball out in the Arizona desert where it’s been mid-80s and sunny since I arrived on Thursday.
Chicago Cubs News / Chicago Cubs on SI / November 9
How Cubs Dramatic Future Payroll Drop Will Allow Them To Pursue Major Free Agents
This is the time of year for Top 50 free agents lists and projections for salaries for those star players. The projections don’t necessarily line up with reality, but they do set outside expectations for what free agents could get.
Justin Steele News / Chicago Cubs on SI / November 9
Why Cubs Activated Justin Steele from 60-Day IL In Post-World Series Move
Chicago Cubs fans know that left-hander Justin Steele is unlikely to pitch until at least the second half of the 2026 season due to Tommy John surgery.
Shota Imanaga News / MLB on ClutchPoints / November 9
3 teams that should steal Shota Imanaga away from Cubs
The free agency market just welcomed one of its most intriguing available arms—and the Chicago Cubs inexplicably let him walk. Shota Imanaga, the 32-year-old Japanese left-handed starter who dazzled in his rookie MLB campaign, is now available after both sides declined their respective options.
Chicago Cubs News / Bleed Cubbie Blue / November 9
Cubs historical sleuthing: 1970s groovy beard edition
Many of you will likely remember Tim Blackwell, one of the typical “good field, no hit” catchers of the era. Blackwell usually sported a walrus mustache; that’s how I remember him.
Alex Bregman News / Chicago Cubs on SI / November 9
Cubs’ Past $130 Million Alex Bregman Offer Raises Free Agency Questions
The Chicago Cubs have some interesting decisions to make when it comes to attacking this upcoming offseason. While nothing is set in stone right now, the writing seems to be on the wall that Kyle Tucker's time in Chicago has ended.
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.
A.J. Puckett News / ChiCitySports / November 9
1 recent MiLB free agent the Cubs should strongly consider bringing back
On November 6, 26 Chicago Cubs Minor League players officially entered free agency. Of this group, there are a few standouts, one of which is RHP A.J. Puckett.
Chicago Cubs News / ChiCitySports / November 8
2025 KBO star pitcher serves as realistic Cubs free agent signing
The Chicago Cubs were dealt a massive blow recently when Shota Imanaga exercised his ability to opt out of his contract, making him a free agent. Imanaga’s ability to opt out was triggered by the Cubs declining to lengthen his contract to five years instead of four, but now his tenure in Chicago is done after just two seasons.
Chicago Cubs News / Chicago Cubs on SI / November 8
Cubs Could See Next Japanese Ace As Shota Imanaga Replacement
The Chicago Cubs could be without one of their best starting pitchers next season, given that Shota Imanaga declined his one-year, $15 million player option earlier this week, which was the byproduct of the Cubs declining a team option to extend Imanaga's contract for three more seasons and $57 million.
Chicago Cubs News / MLB on ClutchPoints / November 8
Cubs win National League team Gold Glove award
The Chicago Cubs have been named the top defensive team in the National League, winning the 2025 Rawlings Team Gold Glove Award for the second time since the accolade’s inception in 2020.
MLB News / Chicago Cubs on SI / November 7
Why Ex-Yankees Closer Luke Weaver Makes Perfect Sense For Cubs Bullpen
The Chicago Cubs are in a precarious place right now when it comes to their bullpen. This is owed to the team having multiple key pieces to their 2025 relief corps elect free agency heading into this offseason, including Caleb Thielbar, Drew Pomeranz, Aaron Civale, Taylor Rogers, Ryan Brasier, Michael Soroka, and Brad Keller.
MLB News / ChiCitySports / November 7
Chicago Cubs: Stakes and risks in qualifying offers made to Kyle Tucker and Shota Imanaga
The Chicago Cubs are handling some of the messy financial stuff before diving into the more baseball-oriented concerns later in the offseason. Specifically, this has meant trading away Andrew Kittredge (and his $9 million option), declining the option of Justin Turner, and making the choice to hold on to Colin Rea via restructured deal.
Kyle Tucker News / Athlon Sports / November 6
Cubs Announce Kyle Tucker News Amid MLB Free Agency
Kyle Tucker is set to hit unrestricted free agency after one season as a member of the Chicago Cubs. As free agency begins, the Cubs extended the qualifying offer to Tucker on Thursday, a one-year offer worth $22 million.
MLB News / Yardbarker / November 6
Three questions facing the Los Angeles Dodgers this offseason
The Los Angeles Dodgers accomplished something that had not happened since 1999 — becoming back-to-back World Series champions.
Justin Turner News / MLB Trade Rumors / November 6
Justin Turner becomes free agent
Infielder Justin Turner is headed into free agency after his mutual option with the Cubs was declined, according to an announcement by the Major League Baseball Players Association this morning.
Colin Rea News / MLB Trade Rumors / November 6
Cubs, Colin Rea agree to one-year extension
The Cubs have hammered out a restructured deal with right-hander Colin Rea, reports MLBTR’s Steve Adams. It’s a $6.5MM guarantee that includes a club option for the 2027 season and maxes out at $13MM over two years if that option is exercised.
Chicago Cubs News / Total Apex Sports / November 5
Chicago Cubs 2025 Offseason Outlook
The Chicago Cubs made the postseason this year for the first time since 2020. They finished 92-70 and finished 2nd in the NL Central. The season was a step in the right direction for a franchise that came into this year with a lot of uncertainty.
Chicago Cubs News / Larry Brown Sports / November 5
Kyle Tucker's stunning contract demand is revealed ahead of free agency
The Chicago Cubs’ marriage with outfielder Kyle Tucker appears likely to be short-lived.
Chicago Cubs News / MLB Trade Rumors / November 5
Cubs not expected to pursue top free-agent relievers
The Cubs are going to need to overhaul their bullpen this winter after trading Andrew Kittredge to the Orioles yesterday while Brad Keller, Drew Pomeranz, and Caleb Thielbar are all ticketed for free agency.
Shota Imanaga News / Yardbarker / November 5
Cubs make surprising decision on lefty Shota Imanaga
The Cubs made a surprising choice to start their offseason.
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