Fly The W

The win. The parade. The memories. Roy and Matt go through their best stories from the aftermath of Game 7, and a host of special guests share their memories of that magical afterglow: Sarah Spain, Chris Hayes, Jessica Smetana, Jeremy Piven, Ryan Dempster, Katie Rich, David Ross, Joe Maddon and more!

The rain delay. The locker room speech. The comeback. Game 7 hero (and current Cubs manager) David Ross joins to discuss how the Cubs finally won it all in the most dramatic way possible.

Wrigley hosts two more games and the Cubs, somehow, start to work their way back into the series from down 3-1. ESPN’s Sarah Spain joins to discuss down the games and key moments, plus talk about her unique approach to Cubs fandom -- and an epic Bill Murray story.

The World Series begins and things don’t go so well for the Cubs. Roy and Matt break down the first three games, including the return of the World Series to Wrigley Field, and the emerging storylines that would set up an incredible back half of the series.

The Cubs are in the World Series for the first time since 1945. Roy and Matt discuss what the moment meant for Chicago, the history of Cubs and White Sox fandom, and how nervous Chicago was at this moment. Then legendary sportswriter Tom Verducci joins to talk about what really made that team special.

Roy and Matt dive back into the run and break down the Cubs vs. Dodgers series, which saw a game 5 comeback where the Cubs finally showed what they were made of. Plus Cubs play-by-play announcer Pat Hughes talks about his approach to calling games, and what it was like at Wrigley Field when the Cubs finally made it back to the World Series.

Theo Epstein did it in Boston, and then again in Chicago. He joins Matt and Roy to talk about the way in which the Cubs culture was rebuilt from top to bottom during his time as president of baseball operations.

The Cubs had a brilliant regular season, but the Giants always seemed to find a way in October. Plus, special guest Katie Rich (Chicago Party Aunt) talks about the culture of Wrigleyville, and balancing watching the 2016 Cubs while writing for SNL.

Joe Maddon is one of the most unique managers, and personalities, in baseball. He joins Matt and Roy to discuss how he balanced analytics and “feel” with the 2016 Cubs, and how Cubs fans should look back at the squad that has since been broken up.

Roy and Matt introduce you to the cast of characters who made the 2016 run possible. Then, they take a tour through 108 years of heartbreak, and are joined by former Cubs ace Ryan Dempster -- who may or may not believe in The Curse of the Billy Goat.