HBO and The Ringer's Bill Simmons is joined by his old friend and rival Yankees fan JackO to discuss the Red Sox's sweep of the Yankees, A-Rod's relentless commentary, playoff implications, and more (3:38). Then Bill sits down with his daughter, Zoe, to discuss teen culture in the form of breakups, YouTube, and TV (39:30), before talking with Chris Ryan about the season finale of HBO's 'Succession' (1:04:05).