Wrigleyville Nation's Podcast - Chicago Cubs Discussion, News, & More · wrigleyvillenation.com

Ep 396 - Guest: Matt Trueblood, Imanaga Opts Out, World Series Lessons Learned, Cubs Offseason Options, & More

November 5, 2025·1 hr 22 min·35 clips

Jeremy and Pat mark episode 396 with a 12-year anniversary check-in. They note the show has now passed 406 total episodes once the special shows are counted in. Matt Trueblood returns as a longtime friend of the show, and the opening joke reaches back to 2013. After a little banter, the conversation settles into Cubs roster talk. The episode follows a familiar Wrigleyville Nation shape: a little reminiscing, then a long argument about how the team is built. The hosts and Matt work through the Cubs' offseason posture and what it really means to build a team with real constraints. Jed Hoyer's willingness to negotiate, and Tom Ricketts's budget habits, become central to the discussion. They push on the idea that money exists in theory, but not always in the form the market wants. Deferrals get a long look. The conversation treats them as a financial tool, not some magic cheat code. That opens into a broader question about why the Cubs have been reluctant to use the kinds of structures many players now prefer. One possible answer is simple ownership caution around long-term liabilities, especially if the team ever plans to be sold. Another possibility is the belief that player costs may look different after the 2026 season. Shota Imanaga comes into that same planning puzzle as part of the day's big news, not as an isolated headline. Matt Trueblood helps keep the discussion grounded in the practical side of roster construction rather than letting it drift into empty outrage. The episode closes with a shoutout to the Cubs' 2025 Gold Glove winners, Nico Horner, Ian Happ, and Pete Gromstrom. The whole episode feels like a long, slightly dry, well-informed Cubs group chat that keeps circling back to the same question: what kind of offseason can this team realistically have?

As heard by us

A sharp Cubs offseason conversation that treats budget math and roster logic as the real stakes.

Wrigleyville Nation uses its anniversary episode to do what it does best: turn Cubs offseason noise into a plainspoken argument about money, structure, and how much patience a front office can reasonably ask for.

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Why you'd press play

For when you want the Cubs offseason argument with real roster consequences.

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