Welcome to Episode #145! We bring on friends Nathan and Jon for a 3-man weave covering a wide variety of topics in the world of Bill Simmons. (0:00-25:30) We start off reminiscing about becoming fans of Bill many years ago. The sports media landscape was vastly different and Bill's writing, and later podcasting, were revolutionary. We identify what enabled him to surpass peers, stay ahead of those emulating his style, and how impressive it's been that Bill's been relevant for three decades across several mediums. Plus, he's done an excellent job of cultivating and coaching talent. (25:30-46:00) We next discuss how the guys have bonded with peers in DC by referencing Bill, including attending events in a Heat movie poster t-shirt. In a highly political world, especially living and working in the nation's capital, The Ringer's content is an escape from the day to day, and the shows are a refreshing alternative to Rogan, hitting on more varied topics. We do wonder, though, why Bill sat out the "podcast election" in 2024 and whether The Ringer will change that in 2028 and beyond. (46:00-59:00) We contrast Barstool and The Ringer and identify how the latter has more interesting and nuanced takes on sports and pop culture which keep listeners coming back, compared to Barstool's more inconsistent shock value attempt at entertainment. We get into Russillo's move and why fans of him and Bill together haven't followed him to Barstool; he's a great #2, but the roster at his new home doesn't have the same depth of people he can play off of like he used to have. (59:00-1:17:00) Next we get into one of Bill's most divisive guests, Derek Thompson - who Nathan knows in real life, yet is blocked by him on Twitter. While we at times enjoy Derek on Bill's pod, we have issues with how he presents his guests and their views and how he often clouds the audience of knowing his and his guests' bias. He will also buy into the hype on topics before doing a quick 180. We have a spontaneous review of Derek and Ezra Klein's Abundance book and discuss the movement in general (1:07:50) before articulating why we like "big ideas" guests Gladwell and Klosterman over Derek. (1:17:00 -1:24:45) Speaking of Klosterman, we look back on his epic Sophie Cunningham call. Jon, who is a WNBA fan and thinks the product has never been better, offers his takes on how the WNBA can fix things, including a very Simmons-esque idea of making Sophie a player commish. (1:24:45-1:38:45) We next get into Bill Simmons current events including his Anduril hat, in which we theorize his motivation for wearing it and how he actually got it, Bull Simmons Instagram reels, Bill's dad as a Pantheon guest and the Jimmy Kimmel situation. (1:38:45-1:53:00) Given Jon and Nathan's backgrounds, we discuss why is there no conservative Ringer. Jon sees parallels to Christian media, which in his view has often failed because the first goal is to push a message instead of the art itself being the point. Contrasting this with The Ringer, their aim is to make entertaining content about sports and pop culture, and while some politics may come out, it's not the focus; Hollywood can be similar in this way. We also hit on (1:44:30) which Ringer podcasters would be the most likely to run for office (CR, Van, Mallory). (1:53:00-2:07:30) We next talk Ringer current events, including more analysis of Sean and Amanda's comments on the Talk Easy pod, and predict there could be some internal issues at The Ringer because of those dynamics; would Sean & Amanda ever leave? We also assess Bill's role in sports gambling and wonder if Bill is vulnerable to being cancelled because of it. (2:07:30-2:21:10) We finish up stating why Bill is underrated as a sports columnist and hope he writes a biography one day. If you liked the pod, follow Jon (@JonSchweppe) and Nathan (@NathanLeamerDC) on Twitter.
