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The Bill Simmons Podcast

NFL Over/Unders, an Oscars Preview, and a Brady-Pats Feud | With Cousin Sal, Sean Fennessey, and Seth Wickersham

171 min episode · 3 min read
·
Sean Fennessey,Seth Wickersham

Episode

171 min

Read time

3 min

Topics

Relationships, Investing, Fundraising & VC

AI-Generated Summary

Key Takeaways

  • NFL Schedule Impact on Win Totals: Schedule difficulty drives FanDuel's over/unders more than roster quality. The Patriots drop from 14 wins to a 9.5 projection — a 4.5-game swing — entirely because they shift from a first-place schedule to a harder slate. Similarly, Denver falls from 14 wins to 9.5. When a team's win total drops 4+ games year-over-year, the schedule differential, not roster regression, is typically the primary explanation worth investigating before betting.
  • Early Over/Under Betting Strategy: Lines move between release and August, so identifying which totals will rise lets bettors lock in value early. The Chargers at 9.5 are flagged as a line likely to climb to 10.5 once roster moves and draft picks are factored in. The Giants at 7.5 are similarly identified as a number that could rise as public sentiment builds around their new coach and returning quarterback Jaylen Daniels.
  • Division Win Total Arbitrage: Comparing division-wide projected wins reveals market inefficiencies. The NFC South projects at just 29 total wins across four teams, with Carolina and New Orleans each sitting at 6.5. When an entire division projects this low, individual team overs carry better value because the soft schedule — NFC North and AFC North opponents — creates realistic paths to seven-plus wins even with limited rosters.
  • Two-First-Round Trade Historical Failure Rate: Trading two first-round picks for a single player has a historically poor success rate. A compiled list of such trades includes Herschel Walker, Ricky Williams, Keyshawn Johnson, Jalen Ramsey, Khalil Mack, Jamal Adams, and Russell Wilson. The only defensible success is Matthew Stafford, and that trade also included Jared Goff going the other direction, complicating the valuation. Baltimore's Max Crosby trade fits this pattern and warrants skepticism.
  • Best Actor Race Volatility: The Oscar best actor category is unusually unpredictable when SAG has only correctly predicted the Academy winner three out of the last six years. Michael B. Jordan is a slight betting favorite despite winning zero precursor awards before SAG. Timothée Chalamet has dropped to plus-145 range after being a prohibitive favorite. Wagner Moura at 20-to-1 represents a live dark horse given Brazil's academy bloc and his precision campaigning strategy.

What It Covers

Bill Simmons, Cousin Sal, Sean Fennessey, and Seth Wickersham cover three topics across 171 minutes: FanDuel's newly released NFL win total over/unders for all 32 teams, Oscar predictions ahead of Sunday's ceremony with best actor race analysis, and Brady's complicated relationship with the Patriots organization drawn from Wickersham's book American Kings.

Key Questions Answered

  • NFL Schedule Impact on Win Totals: Schedule difficulty drives FanDuel's over/unders more than roster quality. The Patriots drop from 14 wins to a 9.5 projection — a 4.5-game swing — entirely because they shift from a first-place schedule to a harder slate. Similarly, Denver falls from 14 wins to 9.5. When a team's win total drops 4+ games year-over-year, the schedule differential, not roster regression, is typically the primary explanation worth investigating before betting.
  • Early Over/Under Betting Strategy: Lines move between release and August, so identifying which totals will rise lets bettors lock in value early. The Chargers at 9.5 are flagged as a line likely to climb to 10.5 once roster moves and draft picks are factored in. The Giants at 7.5 are similarly identified as a number that could rise as public sentiment builds around their new coach and returning quarterback Jaylen Daniels.
  • Division Win Total Arbitrage: Comparing division-wide projected wins reveals market inefficiencies. The NFC South projects at just 29 total wins across four teams, with Carolina and New Orleans each sitting at 6.5. When an entire division projects this low, individual team overs carry better value because the soft schedule — NFC North and AFC North opponents — creates realistic paths to seven-plus wins even with limited rosters.
  • Two-First-Round Trade Historical Failure Rate: Trading two first-round picks for a single player has a historically poor success rate. A compiled list of such trades includes Herschel Walker, Ricky Williams, Keyshawn Johnson, Jalen Ramsey, Khalil Mack, Jamal Adams, and Russell Wilson. The only defensible success is Matthew Stafford, and that trade also included Jared Goff going the other direction, complicating the valuation. Baltimore's Max Crosby trade fits this pattern and warrants skepticism.
  • Best Actor Race Volatility: The Oscar best actor category is unusually unpredictable when SAG has only correctly predicted the Academy winner three out of the last six years. Michael B. Jordan is a slight betting favorite despite winning zero precursor awards before SAG. Timothée Chalamet has dropped to plus-145 range after being a prohibitive favorite. Wagner Moura at 20-to-1 represents a live dark horse given Brazil's academy bloc and his precision campaigning strategy.
  • Overexposure Risk for Award Frontrunners: Chalamet's trajectory illustrates how marketing campaigns that successfully open original films — Marty Supreme reaching 100 million dollars — can simultaneously generate voter fatigue. The same visibility that proved his box office viability as a standalone star created an "enough of this guy" reaction among academy voters. The lesson: aggressive IP-free film marketing and awards campaigning simultaneously is a high-risk strategy that can erode goodwill with voting bodies.
  • Fourth-Place Schedule as Betting Signal: Teams finishing last in their division receive easier schedules the following year, creating a reliable over betting signal when combined with coaching changes or quarterback upgrades. The Giants at 7.5 coming off four wins, the Titans at 6.5 with a new coach and Cam Ward in year two, and the Raiders at 5.5 with Gardner Minshew all fit this profile. Historically, these setups have produced two-to-four win improvements over projections.

Notable Moment

During the Oscar discussion, Fennessey reveals that One Battle has won every major guild award — producers, directors, SAG ensemble, cinematography, and editing — yet Sinners has won zero precursor awards at any show. For Sinners to win best picture would represent one of the most statistically unprecedented upsets in Academy Awards history based on precursor data alone.

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Episode Transcript

This episode is brought to you by State Farm. Imagine a game where you're on the court solo. No coach, no teammates, no one in the stands. Stressful. Right? Sometimes life can feel like that too. That's when State Farm, they show up. They're on the bench, ready to help you find the right coverage when it matters most through an agent online or even on the app. State farm with the assist coverage options are selected by the customer availability and eligibility vary by state. The bill Simmons podcast is presented by Sam's club. We are also presented by the ringer podcast network, where we put up a new Rewatchables episode on Monday night. It was the second movie of CR month. Me, Chris Ryan, Kyle Brandt, we did Fargo. Thirtieth anniversary of the movie this week too. So it was fun timing for that one. Had a great time. Next movie that's coming, Monday night is gonna be to live and die in LA, which if you have not seen it, just an all time eighties movie. If you liked heat, if you liked these gritty crime dramas, highly recommend. So you have a few days to check that one out. We have an action packed podcast on this one. Cousin Sal and I are gonna break down all the NFL over unders that just came out on FanDuel, and our instant reactions to that. Sean Fennessy, we're talking Oscars because the Oscars are Sunday night. He's going live on Netflix. And, we had to talk about best actor and some of the other subplots that popped up. And then if that's not enough, in this action packed gigantic podcast, our old friend Seth Wicker Sham came on to talk about Brady's bizarre relationship with patriots and, everything we've learned about the quarterback position, which he covered in his book, American Kings. So, we have NFL over unders. We have the Oscars. We have the Patriots and quarterbacks all coming next. We're gonna take a break Pearl jam and then cousin. So this episode of the bill summons podcast is presented by Sam's club. It is that time of the year when you just gotta get in your car and go somewhere. I've done that plenty of times in my life. Nowhere gets you ready to go quite like Sam's Club. Snacks, the gear, super low prices on gas. They got a bunch of stuff that keep you and the whole crew rolling. And And here's what you gotta do. You gotta join the club of yes. At sam'sclub.com/yes. And you must be 18 years or older to purchase a membership. A membership is subject to qualifications. Visit sam'sclub.com/yes. And for details. Alright. Recording this part of the podcast, it is 02:45 Pacific time. We got word today, cousin Sal, that FanDuel Sportsbook was gonna release their NFL over unders for Win Total, which we love. I I basically begged them to wait. I was gonna do this …

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