The Ringer's Bill Simmons shares his thoughts on the Dodgers' Game 5 win over the Giants, sending them to the NLCS for the second straight year (2:55). Then Bill talks with NFL Network's Peter Schrager about Jon Gruden's exit from the Raiders, before making their Million-Dollar Picks for NFL Week 6 (22:29). Finally Bill is joined by Jay Caspian Kang of The New York Times to discuss his new book, 'The Loneliest Americans,' as well as a range of NBA topics including Kyrie Irving and the Nets, the limits of NBA analytics, why the Trail Blazers need to trade for Ben Simmons, and more (1:14:30).

Host: Bill Simmons

Guests: Peter Schrager and Jay Caspian Kang

Producer: Kyle Crichton

Learn more about your ad choices. Visit podcastchoices.com/adchoices