Troy Aikman was the first overall pick in the 1989 NFL Draft. He won three Super Bowls with the Dallas Cowboys in the 1990s, was elected to the Pro Football Hall of Fame in 2006, and currently serves as the Monday Night Football commentator for ESPN. We discuss how he initially got into broadcasting, why he left FOX for ESPN after 20 years, his take on Tom Brady’s $375 million broadcasting deal, the future of the NFL, what it’s like owning a professional sports team, his new beer company EIGHT, and much more.