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Offseason Really Gets Going, Gold Glove History and Honors, Heaters, and Other Cubs Bullets

I’m not sure how I would’ve predicted the decade the followed, at least not exactly, but I can say with confidence that I thought the Chicago Cubs would have more on-field success after the 2016 World Series win than they…

Published: Monday, 2 November 2026 at 1:46 PM
Offseason Really Gets Going, Gold Glove History and Honors, Heaters, and Other Cubs Bullets
Key Things to Know
  • Bleacher Nation examines the start of the MLB offseason alongside Chicago Cubs roster decisions and Gold Glove honors.
  • Alex Bregman joined Ron Santo as the only third basemen in Chicago Cubs history to win a Gold Glove.
  • Clay Holmes is widely expected to decline his twelve million dollar player option with the Chicago Cubs.
The Story in 60 Seconds

Bleacher Nation's Brett Taylor analyzes the start of the MLB offseason, reviewing important roster deadlines, contract decisions, and Gold Glove honors. Taylor notes that the five-day exclusive negotiating window is ending alongside deadlines for qualifying offers and contract options. He anticipates that pitcher Clay Holmes will decline his $12 million player option, while expressing hope that the Chicago Cubs negotiate a new deal to retain him as a free agent.

Taylor also highlights Alex Bregman becoming the first Cubs third baseman since Ron Santo to win a Gold Glove award. Additionally, the piece touches on remaining team options for Javier Assad, Colin Rea, and Jacob Webb, while sharing a report detailing the Milwaukee Brewers' clubhouse superstition involving pregame cigarettes during their World Series run.

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