Podcast Summary: The Herd with Colin Cowherd
Episode: Sharp or Square – Last-minute NFL Week 1 bets for Steelers-Jets, Bengals-Browns, Dolphins-Colts, Raiders-Patriots & more
Date: September 7, 2025
Hosts: Chad Millman & Simon Hunter
Network: iHeartPodcasts and The Volume
Episode Overview
This episode features the first “in the room” edition of Sharper Square, with Chad Millman and professional bettor Simon Hunter bringing listeners behind the scenes of their real Sunday morning contest picks for NFL Week 1. The goal: provide their up-to-the-minute decision-making process, highlight bets with sharp versus square (public) lean, address how line movements and injuries influence picks, and give contest advice rooted in experience. Listeners get a genuine, fast-paced window into the tension, regret, and last-minute pivots that accompany high-stakes sports betting.
Key Discussion Points & Insights
The Contest Approach & Mindset
- Transparency: Chad and Simon commit to sharing their genuine, sometimes panicked decision process, resisting the urge to be overly polished or change picks last minute due to “Sunday morning panic.”
- Quote: “We’re like all of you, right? The Sunday morning panic is real.” (Simon Hunter, 03:49)
- Line Shopping & Value: Emphasis on maximizing line value—picking numbers locked earlier in the week when they’re more favorable, and explaining why they might pass on a side if value is gone.
- Quote: “We’re sticklers. We might annoy you… we always want the best of the number.” (Simon Hunter, 05:58)
Week 1 NFL Picks – Game-by-Game Breakdown
1. Tennessee at Denver
- Line: 7.5 (contest), 8 (live)
- Simon has a soft spot for Tennessee but balks at including them since the contest line isn’t as good as he'd like.
- Quote: “If this number lands on eight and we lose this contest, I would lose my mind.” (Simon Hunter, 06:38)
2. LA Chargers (already played)
- Line: 3.5
- Celebratory mention: Already 1-0 on the week, consensus sharp pick.
3. Cincinnati at Cleveland
- Line: Cleveland +5.5
- Both hosts love Cleveland; Simon locked this in on Tuesday and calls it a fundamental play for the contest.
4. Baltimore at Buffalo
- Line: Contest has Ravens +1.5; market had moved to Baltimore as favorites
- Comfortable taking Ravens even if line has flipped, due to matchup edge with Ravens’ offense vs. Bills’ suspect secondary.
- Quote: “This is regular season Lamar. This is exactly where you want to back them.” (Simon Hunter, 08:49)
5. Detroit at Green Bay
- Line moved, value gone
- Chad passes on Detroit with line dropping from +2.5 to +1.5, standing firm on only playing the best value.
6. Pittsburgh at NY Jets
- Line: Jets -2.5
- Divided feelings: Sharp money has come for Jets, but value at 3 is gone. Simon says, “Just other games I love more.” (12:17)
7. Las Vegas at New England
- Line: Raiders +2.5
- Similar sentiment as Jets: like the side, but didn’t make the Tuesday shortlist. Simon raises concerns about being “too blind” to his season-long Raiders enthusiasm.
8. San Francisco at Seattle
- Line: Seahawks +2.5 (contest value), down to +1 most books
- Simon loves Seattle at contest +2.5, citing key injuries for SF and scheme/defense matchups favoring Seahawks. Secondes Chad’s expectation this would be his “value” pick at this number.
9. Carolina at Jacksonville
- Line: Jags -2.5 (contest), moved to -4.5 elsewhere
- Contest line is “too good to pass up” per Simon. Both hosts contemplate including the Jaguars as their rare favorite.
10. Miami at Indianapolis
- Line: Miami +1.5
- Chad is adamant on Miami, feels it’s an ideal spot against a banged-up Colts secondary, and feels relief Simon puts it on the table.
Final Card and Close Calls
- Locks (final decisions):
- Chargers -3.5 (already played, win)
- Cleveland +5.5
- Baltimore (+1.5 contest, ok up to -2)
- Miami +1.5
- Jacksonville -2.5 (contest line, despite hesitations)
- Left Out, Viral Debate:
- Seattle (+2.5) and Tennessee (+7.5) passed over due to line issues
- Raiders/Jets considered but deprioritized due to loss of key number (3)
Memorable Moment (Line Value):
“That’s our Achilles heel, people. If you’re new to the show: We only pick dogs. ...We don’t have a single favorite pick!” (Simon Hunter, 20:35)
Notable Quotes & Memorable Moments
- On the Sunday Morning Routine:
- “It was just us basically arguing and debating with each other over the final five picks… We decided... we’re gonna let people into the room where it happens.”
— Chad Millman, 02:35
- “It was just us basically arguing and debating with each other over the final five picks… We decided... we’re gonna let people into the room where it happens.”
- On Line Discipline:
- “We are sticklers about it because we’ve been burned by the half a point.”
— Simon Hunter, 05:58
- “We are sticklers about it because we’ve been burned by the half a point.”
- On Baltimore as a Pick:
- “This is regular season Lamar. This is exactly where you want to back them.”
— Simon Hunter, 08:49
- “This is regular season Lamar. This is exactly where you want to back them.”
- On Passing on Detroit (Value Gone):
- “I don’t want to force this in at all. We’re not getting the best of the number.”
— Chad Millman, 10:24
- “I don’t want to force this in at all. We’re not getting the best of the number.”
- On Seattle and Line Value:
- “It’s really about the number. +2.5, we love it… This feels like divisional game, close and grueling, home divisional dog Week 1. Yeah, I can’t avoid it.”
— Simon Hunter, 15:45
- “It’s really about the number. +2.5, we love it… This feels like divisional game, close and grueling, home divisional dog Week 1. Yeah, I can’t avoid it.”
Timestamps for Important Segments
- Show format & intent: 02:12–04:28
- How line value impacts choices: 05:58–07:20
- Game-by-game discussion starts: 05:00
- Tennessee/Denver: 05:00–07:20
- Chargers: 07:22–07:46
- Cincinnati/Cleveland: 07:59–08:19
- Ravens/Bills: 08:19–09:31
- Detroit/Green Bay: 09:31–10:53
- Jets/Steelers, Raiders/Patriots: 10:53–13:42
- Seahawks/49ers: 14:05–16:18
- Jaguars/Panthers: 18:40–20:32
- Dolphins/Colts: 21:42–22:55
- Final picks recap: 23:06–23:37
- Contest encouragement & closing: 24:04–24:29
Final Week 1 Contest Picks
- Chargers (-3.5) (already played, win)
- Cleveland (+5.5)
- Baltimore (+1.5, contest; play up to -2)
- Jacksonville (-2.5, contest line)
- Miami (+1.5)
“Hopefully we do the show coming in four-zero, brother. So yeah, I’m pretty excited for today and the games ahead.”
— Simon Hunter (24:21)
Conclusion/Tone
This episode is fast, practical, self-deprecating, and focuses on the nitty-gritty realities of last-minute NFL betting. Chad and Simon are transparent about nerves, indecision, and second-guessing, while still modeling disciplined contest strategy. The tone is conversational and honest, offering plenty for listeners seeking an edge—or just the vicarious thrill—of the Sunday sweat.
For further picks and to share yours, head to the Sharper Square YouTube—Simon will post official contest entries before the Sunday night recap.