The Bill Simmons Podcast

Episode: The Mailbag Makes a Dramatic Return

Date: November 18, 2025
Host: Bill Simmons
Podcast Network: The Ringer

Overview

In this lively episode, Bill Simmons revives his iconic listener mailbag, a staple from his early days as the "Boston Sports Guy." Taking questions from fans, Simmons covers a vast range of topics: sports history, NBA trades, funniest movie deaths, team realignment, pop culture, and his own signature conspiracy theories. The episode is a blend of in-depth sports analysis, nostalgic humor, pop culture riffs, and fan engagement—classic Simmons.

Key Discussion Points & Insights

1. The Mailbag Returns: History and Intent

• [05:54] Bill explains the mailbag’s origins, tracing it back to 1997, inspired by David Letterman’s viewer mail and his desire to differentiate himself from traditional columnists.
• “It started in 1997 and now it’s 2025. I can’t believe this is still going.” [05:58] – Bill Simmons
• He promises a mix of serious and goofy questions, embracing the “spray-on hair” comeback analogy.

2. Signature Concepts & Listener Callbacks

“Wins Above Raheem Morris” (WARM)

• [12:10] Revisiting his old football metric, WARM, Simmons debates its namesake, argues it’s still relevant, and muses about renaming it "WARC" for Romeo Crennel.
• “WARM works. If you’re talking about futures, yes.” [13:40] – Bill Simmons

Highest Acting "WAR"

• [17:40] Discusses which actor had the highest “wins above replacement” for a role.
• Clear answer: James Gandolfini as Tony Soprano.
• “It’s the greatest TV acting performance of all time. I have it, number one.” [19:12] – Bill Simmons

3. Quick Hits: Classic and New Mailbag Bits

Making Fun of Age

• Playful back-and-forth as listeners rib Bill about his increasing age; he insists he feels “spiritually young” [09:45].

Nicknames for Sam Darnold

• [23:52] Listener suggests “Benedict Darnold” for Sam's notorious turnovers.
• “That’s amazing. I don’t know how we didn’t think of that.” [24:20] – Bill Simmons

LeBron as Corporate Raider

• [25:48] Compares LeBron’s championship methods to a leveraged buyout.
• “He’s basically a one-man Bain Capital, except he actually gets hundreds of millions and a parade for it.” [26:05] – Listener

The Nico Harrison Award

• [29:40] New Rewatchables category for the worst in-the-moment movie decisions, inspired by the Mavericks’ infamous Luka trade.
• “I think the Nico Harrison Award for worst decision… should just be in there.” [30:21] – Bill Simmons

4. Sports Debate & Analysis

Trump’s Biggest Sports Fan-Triggering Move

• [39:49] Theorizes Trump interfering with the Masters at Augusta would drive fans wild.

NBA “Sliding Doors” Moments

• [45:20] Discusses the impact of the Pistons taking Darko over Carmelo, but calls Draymond’s 2016 NBA Finals “nutshot” on LeBron the real franchise-altering event.
• “It all comes back to Draymond, who may or may not have intentionally hit LeBron on the balls.” [52:20] – Bill Simmons

Patriots Super Bowl Trade-Offs

• [56:05] Bill would give up multiple Pats titles for the “19-0 perfect season” in 2007.

NBA/Fanbase Realignment & Expansion

• [1:02:44] Proposes how the NBA could realign with Vegas and Seattle expansion; Memphis and New Orleans to the East, Milwaukee to the West.
• “I just solved it.” [1:04:19] – Bill Simmons

Weirdest, Most Irrelevant Franchise

• [1:30:42] Crowns the Columbus Blue Jackets as pro sports’ most forgettable team.
• “I have never heard a single convo about them... Unbelievable.” [1:32:55] – Bill Simmons

5. Pop Culture Playground

Eddie Murphy Documentary Review

• [1:16:37] Praises Netflix’s "Being Eddie," longing for even more in-depth 80s focus.
• “He was our number one.” [1:18:24] – Bill Simmons

Funniest Movie Deaths

• [1:22:50] Discusses classics such as Ben Tramer in "Halloween II" and Steven Weber’s character in "Single White Female."

Claire Danes & “The Beast In Me”

• [1:39:50] Names "The Beast in Me" with Claire Danes as his favorite 2025 TV show.
• “This show is a put the iPad down show.” [1:41:10] – Bill Simmons

6. Outlandish Listener Questions & Conspiracies

Simmons’ “All-Star” Favorite Under-the-Radar NBA Players

• [1:10:22] Includes Guy A (Atlanta), Krechi (Atlanta), Keda (Celtics), Quentin Jackson (Pacers), Jordan Goodwin (Suns), and Naquan Tomlin (Cavs).

NBA Sumo Yokozuna Status

• [1:47:12] Riffs on which NBA players/coaches would reach "yokozuna" (sumo champion) status, e.g., Mikan, Russell, Kareem, Bird, Magic, Jordan, etc.

NBA Conspiracy Scale

• [1:55:00] Details his top-10 NBA conspiracy theories, from the “frozen envelope” (10/10) to the Draymond Finals suspension (7/10).
• “The frozen envelope is still the best one.” [1:57:32] – Bill Simmons

On Podcasts and Dated Words

• [1:23:50, 1:25:33] Wonders why “podcast” persists and laughs about words like “knapsack” going extinct.
• “Nobody says the word knapsack. But we did call it a knapsack.” [1:26:19] – Bill Simmons

7. Memorable Listener Exchanges

• T-shirt in the sauna debate: On whether this is sociopathic behavior [41:22].
• Glass Half Empty / Antoine Walker Syndrome: On players fans love but tire of over time [1:20:30].
• Hypothetical Team with Jokic, Luka, Steph, Giannis, and an average guy: Could they win 48 games? [1:28:11].

Notable Quotes & Moments (with Timestamps)

• “It’s like Jalen Brown’s sprayed on hair. You didn’t think it could come back… but there it is, somehow holding together for another run.” – Listener Chris [07:20]
• “Benedict Darnold. That’s amazing. I don’t know how we didn’t think of that.” – Bill Simmons [24:20]
• “He’s basically a one-man Bain Capital, except he actually gets hundreds of millions and a parade for it.” – Listener on LeBron [26:05]
• “The answer here is clearly Gandolfini. It’s not even a question.” – Bill Simmons [19:12]
• "If you could pick one thing from a movie that directly parallels the Luka trade, it's Mayor Vaughn keeping the beaches open in Jaws..." – Bill Simmons [32:35]
• “There’s some Vegas buzz again, I’m just telling you.” – Bill Simmons [1:06:01]
• “I have never heard a single convo about the Blue Jackets…” – Bill Simmons [1:32:55]
• "This show is a put the iPad down show." – Bill Simmons on "The Beast in Me" [1:41:10]
• "The frozen envelope is still the best one." – Bill Simmons [1:57:32]

Important Segments & Timestamps

• [05:54] – Intro and Mailbag origin story
• [12:10] – Reviving “Wins Above Raheem Morris” metric
• [17:40] – Ultimate acting “WAR” debates
• [23:45] – Sam Darnold nickname brainstorm
• [25:48] – LeBron’s “Leveraged Buyout” critique
• [29:40] – The Nico Harrison Award & best/worst pop culture decisions
• [39:49] – Trump’s most incendiary sports moves
• [45:20] – NBA’s greatest “Sliding Doors” moment
• [56:05] – Patriots Super Bowl swap hypothetical
• [1:02:44] – NBA expansion/realignment proposals
• [1:10:22] – Bill’s NBA All-Star “under the radar” faves
• [1:16:37] – "Being Eddie" Netflix doc review
• [1:22:50] – Funniest movie deaths (Jaws 2, Halloween II, etc.)
• [1:28:11] – Hypothetical: “Average guy” on Jokic, Steph, Giannis, Luka team
• [1:47:12] – Sumo “yokozuna” NBA equivalents
• [1:55:00] – NBA conspiracy scale detailed breakdown
• [1:57:32] – Praise for the “frozen envelope” theory

Tone and Language

True to Bill Simmons’ signature style:

• Wry, self-deprecating, and conversational
• Pop culture references intertwined with sports analysis
• Occasional F-bombs (“send sports fans into a fucking frenzy”)
• Deep cut trivia and long-form analogies
• Deep affection for nostalgic moments, running gags, and fan engagement

Summary Takeaways

This episode showcases why the Bill Simmons Mailbag endures nearly three decades after its debut: his keen sense of sports history, enduring rapport with die-hard listeners, joyful banter, and an ability to connect sports, movies, and everyday quirks. Whether debating the nutshots that shifted NBA championships, reminiscing about old sitcoms, spinning new conspiracy theories, or fielding ideas for a Podcast Hall of Fame, Simmons manages to keep both the questions—and his audience—on their toes.