The Mailbag Makes a Dramatic Return

Summary of The Mailbag Makes a Dramatic Return

by The Ringer

1h 29m•November 18, 2025
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Overview of The Mailbag Makes a Dramatic Return (The Bill Simmons Podcast)

Bill Simmons brings back his listener mailbag after a long break, using it as a mix of serious sports analysis and goofy cultural riffs. The episode weaves quick takes on movies/TV, NBA/NFL strategy and history, conspiracy-minded detours, trade proposals, and a return-to-form explanation of his old metrics and recurring bits (like WARM — wins above Raheem Morris). Listeners sent a wide range of questions; Simmons answers them conversationally, often pivoting into pop-culture lists and hypothetical “what if” scenarios.

Mailbag comeback & format notes

  • Origin: Simmons started the mailbag in 1997 on his Boston Sports Guy site; it continued at ESPN and The Ringer before pausing sometime before COVID. This episode is the “virgin” 2025 relaunch.
  • Tone: Intentional mix of serious sports analysis and goofy pop-culture stuff; Simmons asks listeners to continue sending questions to bspodcast33@gmail.com.
  • Logistics: He plans to iterate on format over the next few mailbags and asked listeners for diverse questions (not just NBA).

Key topics and notable Q&A (concise)

  • WARM (Wins Above Raheem Morris)

    • Reintroduced as a preseason NFL futures metric: replacing a bad coach with a good one can be worth ~5–8 wins. Simmons defends the acronym and gives examples (Mike Vrabel, Jim Harbaugh/Chargers).

  • Best “wins above replacement” actor for a role

    • Simmons’s pick: James Gandolfini as Tony Soprano — highest “WAR” because the show and role were elevated by him.

  • Sam Darnold nickname idea

    • Listener proposed “Benedict Darnold” (Benedict Arnold) — Simmons loved it.

  • LeBron as a leverage-buyout operator

    • Fun analogy: LeBron increases franchise value where he goes, wins championships, then leaves; Simmons debates whether that helps or hurts LeBron’s GOAT case.

  • Luca trade / Nico Harrison Award (Rewatchables idea)

    • Simmons plans a Rewatchables category for “worst decision-as-it-happens” (Nico Harrison Award), using examples: Heat’s Neil McCauley in Heat, John Wick 2 dog killing, Titanic necklace, Fredo in Godfather II, Mayor keeping Amity Island open in Jaws.

  • Sliding-doors NBA moment: 2003 draft (Darko over Melo) vs. 2016 Finals (Draymond technical)

    • Simmons picks the 2016 Draymond incident as bigger: if Cleveland loses Game 5 and Golden State wins 2016, Kevin Durant likely never signs with the Warriors — huge downstream effects across multiple franchises.

  • Patriots 19–0 hypothetical

    • Simmons would trade away certain Patriots titles (e.g., 2005 and the final Belichick/Brady Rams win) to buy a 19–0 season in 2007–08; result: immortality via the perfect season and elimination of the “helmet catch.”

  • NBA expansion/realignment (if Seattle and Vegas added)

    • Proposed four 8-team divisions and shifting some teams (Memphis/New Orleans to East; Milwaukee to West); full quick realignment offered in the episode.

  • Celtics trade thought experiment

    • Bill proposes a hypothetical trade to acquire Trey Murphy (Simons/Bey swaps, picks/swaps included) to reshape Boston’s roster if Tatum returns.

  • Trump & sports frenzy

    • Most realistic sports move to enrage fans: Trump meddling with the Masters/Augusta.

  • Most ridiculous movie deaths / Nico Harrison list

    • Simmons ranks worst-on-paper decisions in films and fun death scenes (Jaws 2 gasoline lady, Brent Tram in Halloween 2, Single White Female, Legend of the Fall).

  • “Most irrelevant franchise in pro sports”

    • Simmons: Columbus Blue Jackets — detailed rundown of their history, lack of playoff success, and low profile.

  • Favorite TV of 2025

    • Simmons’s current #1 pick: The Beast in Me (Claire Danes), plus praise for rewatchables origins (Heat) and a positive review of the Eddie Murphy Netflix doc (calls it well done though slightly autobiographical “docu‑mercial”).

  • Miscellaneous

    • Sauna etiquette (t-shirt vs towel) — brief comic debate.
    • Who to watch / players Simmons likes (longshot buy targets like Anthony Simons historically; lists emerging players and under-the-radar guys he’d pursue).
    • Defensive pair “Yokozuna” idea — sets Bill Russell/Casey Jones and Jordan/Pippen as the benchmark.
    • Mike Rice-style “would you rather” sports hypotheticals (e.g., being a 30-minute benchman on a superteam) — Simmons thinks such a team could win ~48 games given modern spacing.
    • Conspiracy Bill segment: ranks NBA conspiracy theories 1–10 (frozen envelope 1984 lottery is #10 — greatest NBA conspiracy).

Notable insights & memorable lines

  • WARM is still useful: coaching changes can create 5–8 win swings — a valuable futures metric.
  • The 2016 Draymond suspension is a genuine “sliding-door” moment: it arguably changed NBA history more than draft mistakes.
  • Rewatchables inspiration: Heat’s Neil McCauley decision is the prototypical “Nico Harrison Award” bad-as-it-happens choice.
  • Simmons often frames sports ideas as “what would you be willing to trade” (e.g., Pats trade-offs for an unblemished season).

Pop-culture & media recommendations mentioned

  • Rewatchables (new episodes weekly; example: Weird Science episode with Kyle Brandt)
  • The Beast in Me (Simmons’s top TV of 2025 so far — Claire Danes)
  • Eddie Murphy: Being Eddie (Netflix) — generally positive, notes it felt somewhat autobiographical but worthwhile
  • Rewatchables episode highlights: Heat, Single White Female, etc.

Action items / how listeners can participate

  • Send mailbag questions to: bspodcast33@gmail.com — Simmons asked for a mix of serious sports analysis and goofy questions.
  • He plans to run more mailbags and iterate the format over several episodes.

Takeaways

  • The mailbag is back with a hybrid approach: smart sports metrics analysis (WARM, sliding-door hypotheticals) mixed with pop-culture riffs and invented awards (Nico Harrison).
  • Simmons remains interested in long-range league impacts (trades, expansions, realignments, and conspiracies) and enjoys building fun categories and hypotheticals listeners can debate.
  • If you want to be part of future episodes, email bspodcast33@gmail.com and strike a balance between thoughtful, analytically minded sports questions and entertaining, offbeat prompts.