The Herd with Colin Cowherd: Sharp or Square – FINAL NFL Week 5 Bets

Podcast: The Herd with Colin Cowherd (iHeartPodcasts and The Volume)
Episode: Sharp or Square - FINAL NFL Week 5 Bets - Cowboys-Jets, Texans-Ravens, Chiefs-Jaguars, Giants-Saints and more
Date: October 5, 2025
Hosts: Chad Millman & Simon Hunter

Overview

This episode of "Sharp or Square" is a lively, betting-focused discussion where professional bettor Simon Hunter and host Chad Millman break down their FINAL picks for NFL Week 5. The pair debate line moves, injury impacts, and key angles while wrestling with betting psychology—debating the relative merits of “going with the sharps” versus “fading the public.” The energy is intense, with both sharing personal sports heartbreak, war stories about gambling, and the agony of last-minute betting decisions.

Key Discussion Points and Insights

1. Opening Stories: Betting Woes and Sports Heartbreak

• Both hosts commiserate about recent losses in baseball and college football before jumping into Week 5 NFL bets.
• Notable Quote – Simon Hunter:
  "I said I would never go again... Feeling good, 3 Nothing... Every move the man made was wrong. Phillies lose 5 3. Honestly, almost as bad as a no hitter walking out." [00:23]
• Chad shares a story about the heartbreak of seeing Maryland blow a huge lead, paralleling the experience to the pain of losing NFL bets.

2. Sharper Square Pick ‘Em Contest Announcement

• A free-to-play NFL Pick’ Em contest is rolling out soon, thanks to Hard Rock Bet. Exact dates forthcoming.
• Chad:
  "Thanks to our magnificent benefactors at Hard Rock Bet ... a free Sharper Square NFL Pick ‘Em contest will be launching in a few weeks. Get excited folks." [01:06]

3. NFL Week 5 Contest Bets—Pick-by-Pick Discussion

a. Rams Loss (Already in the Books)

• Recap: The Rams were a Thursday night pick that lost. The hosts defend the logic behind the bet despite the loss.
• Simon:
  "They had to lose that game in a million different ways for you to lose... That’s why Survivor’s so tough." [03:35]
• Chad:
  "I saved myself three hours of misery by going to bed at halftime." [04:08]

b. Texans (+3.5) vs. Ravens

• Locked in at +3.5 though Texans are now favorites due to market line movement.
• Both agree it’s a must-play, following the sharp money and injury information.
• Simon:
  "Lock it in. That's a quick one. Three and a half. Gotta take it for Houston." [05:02]

c. Saints (-1.5) vs. Giants

• Originally marked as a top bet but both express waning confidence as the line moves.
• Danger of “catching a falling knife”; most sharps still favor Saints but that makes the hosts uneasy.
• Simon:
  "I, I'm leaking confidence as the week goes along because it is the Saints and it's, it's a little scary... But I'm getting a little worried..." [05:55]

d. Jets (+2.5) vs. Cowboys (Brass Balls Bet of the Week)

• High-stress pick, loved for the situational angle and value but acknowledged as gut-wrenching to watch.
• Market moved sharply towards the Jets; sharps are aligned.
• Simon:
  "Every pro I’ve talked to is right there with us, but luckily for us, every public guy I’ve talked to is on the Cowboys…so yeah, this is pros vs. Joes." [08:06]
• Both would still take Jets +1.5 if +2.5 is gone.

e. Chiefs vs. Jaguars (+3.5)

• Chad’s "favorite bet of the week". Simon is less enthusiastic but willing to include based on the number and sharp calls.
• Disagreement over process: pride versus focusing simply on winning bets week-to-week.
• Simon:
  "If you believe in it, you love it. I'm happy to put it in because I think it's a good number...If this is your winner of the week, give it to me." [10:29], [11:03]

f. Broncos (+4.5) vs. Eagles ("Rock and a Hard Place" Bet)

• Both like the number and matchup (Broncos unlucky, Eagles lucky), but wary of why the line moved back up.
• Simon:
  "It's another game where I'm a little scared that there's a blind spot here ... everyone knows there's something wrong with this Eagles team." [14:32]
• Weighing comfort in taking a strong defense plus points (Broncos) over sinking confidence in Saints.

g. Commanders (+2.5) at Chargers

• Simon feels his model may still undervalue injuries for the Chargers.
• Both lean toward Commanders, prefer 3 but will take 2.5; agree it's a better pick than Saints.
• Simon:
  "We're putting faith in the number with the books here. Honestly, if we're back in the Commanders here, Chad...I would still play it." [17:28]

h. Final Pick Decisions (The "Switch")

• Process of elimination has them drop Saints in favor of Commanders.
• Final four for contest (after Rams loss): Texans, Jets, Jaguars, Commanders.

Memorable Quotes & Moments

• On Betting Psychology & Process:
  • Simon [11:25]: "You're too micro right now. Sports betters do not think the way you're talking right now...you're sounding very immature."
  • Chad [11:40]: "I'm not immature. I'm just a dude who was hanging out at the Turf, drinking beers in College Park till late on Friday night with college kids. That's not immature."
• Self-Deprecation & Running Bit:
  • Chad [06:55]: "This might be the fifth or sixth one [pick], right?"
  • Simon [06:30]: "You don't want...everyone with us. I want to at least hear one, one or two other guys breaking me, breaking it down."
• Ultimate Dread/Elation of Betting:
  • Chad [20:27]: "Every time I want to say Denver, I actually want to put the Commanders in. Every time. I feel so regretful. Every time I say Denver."
  • Simon [20:47]: "I won't make us bet against the Chargers if it's under three."
• On Value and Shopping Lines:
  • Simon [08:06]: "This is pros versus Joe's. Good number. Good spot. I already know a thousand different ways we're going to lose this bet. But we're getting a great number."
  • Chad [20:47]: "Let's not discount the number...the number is a big deal."

Timestamps for Key Segments

• [00:02] Personal sports misery stories; contest announcement.
• [03:35] Rams recap and Survivor heartbreak.
• [05:02] Texans (+3.5) over Ravens analysis.
• [05:55] Saints-Giants line flip discussion; waning confidence.
• [08:06] "Brass Balls" Jets pick; pros vs. public on Cowboys-Jets.
• [10:25] Chiefs-Jaguars debate; disagreement over contest strategy.
• [14:24] Broncos (+4.5); line movement and luck/unluck matchups with Eagles.
• [16:17] Commanders (+2.5) vs. Chargers; digging into Jaden Daniels’ injury and market stance.
• [18:50] Process of elimination; Saints dropped, Commanders in.
• [21:04] Final bet recap and outro.

Final Picks for Week 5 (Contest Lines)

1. Texans +3.5 @ Ravens
2. Jets +2.5 vs. Cowboys
3. Jaguars +3.5 vs. Chiefs
4. Commanders +2.5 @ Chargers

• (Rams – Thursday night loss; not part of live Sunday contest)

Tone & Takeaways

The episode is energetic, relatable, and filled with inside jokes and the raw emotions of gambling—trepidation, over-analysis, and the agony of last-minute switches. Chad and Simon show the real struggles of making contest picks when the landscape changes throughout the week. Their chemistry, sharp/funny banter, and willingness to question themselves (“We will lose whatever game we keep in its place”) make this an excellent listen for sports bettors seeking insight, validation, and a reality check.