The Cubs Win Podcast

The Cubs are having as good of an offseason as you could’ve hoped for. Tom Ricketts seems to have broken the narrative by handing out a lucrative contract to Alex Bregman, as he looks to lead the 2026 squad. Jed Hoyer went out of his comfort zone to swing a big trade, bringing young flamethrower Edward Cabrera to Chicago. With 3 years of team control, Tyler Zombro and the pitching department will look to build off his breakout season. Also uncharacteristically of Hoyer, roughly $30M was spent on the bullpen for 2026, and it looks like a very solid and trustworthy group. The big moves are likely done, which is fine, as this is the offseason Cubs fans have been waiting for since the mid-late 2010s.

With Kyle Tucker likely walking, the Cubs will have to find a way to replace his value. We talk about how they could do that.

For the first time since 2017, the Cubs have won a postseason series. Now, things get way more interesting as they face a division rival in the next round.

The stage is set.

For the first time in the history of this podcast, we will get to cover the Cubs in the postseason! We discuss that and everything else that has happened the past couple weeks, including Anthony Rizzo retiring as a Cub.

Despite the standings, the Cubs won the season series against Milwaukee, going 7-6. Owen Caissie finally got the call to the majors, and he had an impact in this series. Cade Horton has arguably made the biggest impact in the 2nd half of the season, though. We talk about how fantastic he has been on the mound. The Cubs made a couple moves for September call-ups, we go over them as well. We also give our August awards.

The Cubs had a trade deadline that many would consider disappointing. @chicagocubscave comes on to discuss the moves. On top of that, the Cubs have been playing not so well lately. Worst of all, Cubs legend Ryne Sandberg sadly passed away. We discuss his legacy in Chicago. It’s also a new month, so that means we hand out our monthly awards for July.

The Cubs are all in this year, and are bound to make some big trades to turn this club into even more of a World Series contender. We go over rumored names, give some mock trades, and say what our expectations are. @1060_media comes back on again to talk about all 20 picks the Cubs made in this year’s draft, going in depth for each selection.

With the draft nearing, @1060_media joins this episode to discuss who the Cubs could or should take at pick 17 and give a full first round mock. On top of game recaps and roster moves, we also talk about who was chosen to be all-stars this year for the Cubs. June monthly awards are given out as well.

The Cubs have finally played their long time rival Cardinals for the first time in 2025, we break down that series and the other games played. We also discuss a plethora of names the Cubs have been linked to in recent trade rumors.