The Jimmy Rex Show #650 - Dexter Fowler - 2016 World Series Hero With Chicago Cubs Reminisces That Series With An Indians Fan
Oct 2, 2025
24:57
On this episode of The Jimmy Rex Show, Jimmy sits down with MLB All-Star Dexter Fowler — the Chicago Cubs leadoff catalyst from the historic 2016 World Series run. They relive Game 7 in Cleveland, from Fowler’s tone-setting leadoff home run to the rollercoaster late innings, the rain delay, and Jason Heyward’s now-legendary clubhouse speech. You’ll hear dugout perspective on Jake Arrieta and Kyle Hendricks, the emotions behind Rajai Davis’s homer, and why the Cubs played looser on the road.
Dexter also shares how he landed in Chicago, what Joe Maddon told him that changed everything, and why the post-title roster couldn’t stay together forever. Then it’s life after baseball: Dexter’s production company, sports & entertainment management, and wealth advisory work; investing (including a stake tied to Bournemouth in English football); and the mentorship lessons he’s picked up from business leaders and friends.
Along the way, Jimmy and Dexter riff on communication, team culture, and having tough conversations — the competitive edge athletes carry into business.
00:00 Introduction
02:43 Game 7 rewind: leadoff HR, momentum swing, rain delay & Heyward speech
08:24 Motivation story: the “Ace of Spades” bottles
09:43 Game 3 at Wrigley: pitcher duels, crowd energy, fan chaos
10:41 After the title: injuries, economics, and the Cubs’ breakup
12:18 Routine vs. noise: why they played looser on the road
13:52 Becoming the Cubs’ leadoff: Iowa preview & Joe Maddon’s trust
17:00 Life after baseball: companies, investments, mentorship & communication lessons
24:06 Outro
Dexter also shares how he landed in Chicago, what Joe Maddon told him that changed everything, and why the post-title roster couldn’t stay together forever. Then it’s life after baseball: Dexter’s production company, sports & entertainment management, and wealth advisory work; investing (including a stake tied to Bournemouth in English football); and the mentorship lessons he’s picked up from business leaders and friends.
Along the way, Jimmy and Dexter riff on communication, team culture, and having tough conversations — the competitive edge athletes carry into business.
00:00 Introduction
02:43 Game 7 rewind: leadoff HR, momentum swing, rain delay & Heyward speech
08:24 Motivation story: the “Ace of Spades” bottles
09:43 Game 3 at Wrigley: pitcher duels, crowd energy, fan chaos
10:41 After the title: injuries, economics, and the Cubs’ breakup
12:18 Routine vs. noise: why they played looser on the road
13:52 Becoming the Cubs’ leadoff: Iowa preview & Joe Maddon’s trust
17:00 Life after baseball: companies, investments, mentorship & communication lessons
24:06 Outro