The Herd with Colin Cowherd

Episode: Sharp or Square – Chad Millman & Simon Hunter’s NFL Week 1 Reactions: Giants-Commanders, Lions-Packers & More

Date: September 8, 2025

Episode Overview

This episode of "Sharp or Square," hosted by Chad Millman with professional bettor Simon Hunter, dives into their reactions, regrets, and lessons from NFL Week 1 betting. Together, the duo breaks down the results of their Contest Picks and personal bets, analyzing the fine line between being “sharp” (professional, value-driven bets) and “square” (public, less-informed decisions). They discuss key games, scrutinize major moments, share their betting philosophies, and preview early Week 2 leans—all with plenty of banter and sharp betting insight.

Key Discussion Points and Insights

1. Week 1 Recap – Results & Philosophy

• Contest Picks Recap: They went 3-1 on their five main picks, with the Ravens pending on Sunday Night Football. Wins: Chargers, Browns, Jaguars. Loss: Dolphins.
• Line Value: Both hosts repeatedly emphasize the importance of getting the best number, noting how marginal differences can determine entire weeks.
  • “That’s why we are such sticklers about it. Getting the best of the number, try to play as safe as possible in the contest.” — Simon (07:12)

2. Bet Breakdown: Hits and Misses

The Dolphins Disaster

• Chad’s Regret: Reluctantly added Miami after Simon brought it up Sunday morning, only to see them flop spectacularly.
• Simon’s Skepticism Confirmed: Simon has been down on Miami all preseason, calling them his “square pick of the week.”
  • “Sometimes it goes the other way. This time it did not. Like you said, they were a train wreck from the start… If I'm gonna lose, that's how I want to lose. Just quick death, it was over.” — Simon (07:25)
• Chad laments Daniel Jones making Miami look even worse:
  • “Daniel Jones looked like Johnny Unitas playing for the Colts… just a pathetic display of a team not being ready, of a team getting blown off the field from the second the game started.” — Chad (07:52)

The Browns (Sharp Bet of the Week)

• Sharp Consensus: Both agreed on Cleveland +5.5.
  • “This was your Simon Says. I wanted it to be Chad Loves, Love. You know, the first drive of the game, I wasn't even worried. Like, this defense was elite...” — Chad (09:52)
• Game Script Analysis: Gumdrops by Browns receivers, missed extra point and field goal, but the defense dominated and the bet was never really in doubt:
  • “There was no point in this game where I felt like the bet was really in jeopardy… they were the much better team today.” — Chad (12:16)
• Philosophy: Betting good defenses, taking mispriced dogs.

Jaguars-Panthers Call

• Disciplined Avoidance: Proud not to have been tempted by the Panthers as public underdogs.
  • “I'm most proud that we never fell prey to the Panthers at +3.5, that we actually played the Jags, followed some line value… that was a last minute move.” — Chad (20:53)

Titans-Broncos & Line Management

• Simon discusses the gut-wrenching nature of betting variants and how coaching can cost underdog covers.
  • “Landing right on 8. That's why I love what we do. It's like that's crazy. That line landed right on eight and... the books were just so sharp with it…” — Simon (23:23)
• Both reiterate that discipline paid off by not putting Tennessee in at the wrong number.

Jets-Steelers: Fun, Chippy, and a Teachable Moment

• Game Flow: Jets were aggressive, with Justin Fields looking strong at QB.
  • “They played with the attitude that we thought Aaron Glenn would bring. And Justin Fields was kind of awesome… Super physical, like they were making a point.” — Chad (25:07)
• Simon: Thrilled with the pick, surprised by the offensive output, and details the importance of key numbers as the game lands on 2.
  • “...the public hammered Pittsburgh minus two and a half. So yeah, the books cleaned up today and usually that’s when we clean up as well.” — Simon (26:28)

3. Early Week 2 Leans & Market Analysis

Miami–New England

• Chad eager on Dolphins bounce-back -1.5:
  • “Miami, first bet I made. Don’t tell me it’s square… I’d bet this game up to 3. Like, you’re gonna have to lean Miami after such a bad showing in week one.” — Chad (29:49)
• Simon nixes contest consideration:
  • “There's zero chance I'm letting you put [Miami] in the contest.” — Simon (30:00)

Eagles–Chiefs

• Both note Chiefs’ injury issues, Philly’s extra rest.
• Early lean to Eagles at +1; Simon ready to adjust if line moves to Chiefs +3.
  • “This number is what you just talked about. It's respect for past years and this is a team that is down their number one and number two wide receiver...” — Simon (32:03)

Chargers–Raiders

• Chad: Chargers overvalued after Chiefs win. Likes Raiders +3.5 “hook.”
• Simon: Likes the lean, notes potential for line move if Bowers is out.

Other Early Leans

• Cincy -5.5 vs Jags: Chad likes Cincy.
• Cleveland +12.5 at Baltimore: Chad sees big value.
• Jets +8.5 vs Bills: Both agree line feels very big.
• Lions -4.5 over Bears: Simon expects line movement; sees opportunity if Bears underwhelm MNF.
• Seahawks +2.5 at Steelers: Simon looking to back Seattle after tough loss.
• Colts +3 at Broncos: Simon surprised by line, likes Colts.
• Panthers +6.5 vs Cardinals: Both see this as egregious; expect to revisit as a sharp play.

Notable Quotes & Memorable Moments

• On Regret and Discipline:
  • “What did I say all week? I said I was not going to make impulsive decisions… And yet [Miami] became a game that I bet and it became a game that we put into the contest. What happened to us?” — Chad (05:14)
• On Being a Professional:
  • “You spent three months gallivanting, traveling the world, writing a book. I was in a hole watching film, crunching numbers just to be told I'm a fraud on the Internet.” — Simon (09:33)
• Simon’s Sharp Bet/Flu Game:
  • “That was my flu game. I was sick as a dog this past week… all week I just kept betting it like I would be sick laying in bed. I'm like, I gotta get up, I gotta go bet this Browns number again.” — Simon (10:52)
• On Avoiding “Landmines”:
  • “There are a lot of landmines out there and that’s the hardest part… I know a lot of really, really smart guys who bet really heavy today on the Falcons, on the Giants and I got their reasoning but it felt lucky that we were on the other side of those.” — Simon (21:43)
• Closing Banter:
  • “You are just feeling yourself right now.” — Chad (39:03)
  • “I just… I'm happy you like Pittsburgh and you have doubts about [Seattle].” — Simon (38:46)

Timestamps for Key Segments

| Segment | Timestamp | |-------------------------------------------|-------------| | Show open, contest results recap | 02:57–05:03 | | The Dolphins debacle | 05:14–09:12 | | Browns “sharp” win | 09:52–13:38 | | Jaguars, Panthers, and following line value| 13:51–16:33 | | Titans-Broncos, line discipline | 21:43–24:58 | | Jets-Steelers breakdown | 25:07–28:05 | | Review of sharp/square decisions | 28:05–30:00 | | Early Week 2 leans (incl. Miami-NE) | 29:49–32:03 | | Eagles–Chiefs, Chargers–Raiders, more | 32:03–34:58 | | Chad & Simon’s rapid-fire Week 2 lines | 35:25–41:22 | | Wrap-up, next show tease | 41:22–42:27 |

Conclusion

With classic mix of self-deprecation and expert analysis, Chad and Simon walk listeners through the emotional and tactical swings of NFL betting. Their ability to own mistakes, celebrate disciplined decisions, and banter about their differences offers both sharp insight and relatable content. The episode closes out with gratitude for listeners and a tease for Tuesday’s upcoming episode.

For anyone tracking sharp NFL betting moves: This is an episode that highlights the agony and ecstasy of contest betting, the crucial importance of line shopping, and the need to balance process with results.