Sharp or Square – FINAL NFL Week 5 Bets
Podcast: iHeartPodcasts and The Volume
Date: October 5, 2025
Hosts: Chad Millman & Simon Hunter

Episode Overview

In this episode, hosts Chad Millman and Simon Hunter lock in their final NFL Week 5 betting picks for their contest, navigating the latest injury reports, line movements, and sharp insight. The show’s goal, as always, is to help casual and serious bettors alike sharpen their instincts—identifying when the pros (“sharps”) and the general public (“squares”) are backing different sides. They debate key matchups, share betting psychology, and deliver their favorite plays, while weighing contest logistics and opportunity cost.

Key Discussion Points and Insights

Opening & Personal Lowlights [02:27–04:00]

• Both hosts share recent sports heartaches: Simon laments attending a Phillies game that turned into a disaster, while Chad details enduring Maryland’s blown football lead during Parents Weekend.
• Quote: “As bad as my life is, I feel thankful I’m not a Phillies-Penn State fan because that is truly the worst life you could have yesterday.” — Simon [02:49]

Sharper Square NFL Pick ’Em Contest Announcement [04:00–06:00]

• New free-to-play contest launching soon, sponsored by Hard Rock Bet. Details pending but listeners are advised to stay tuned for the launch date.

Thursday Night Fallout: Rams Loss [06:00–06:33]

• The hosts recap their unfortunate Rams pick, justifying their process and emphasizing process over results.
• Quote: “Honestly, I’d play it again every time... Home team, short week... We’re not changing that decision.” — Chad [05:49]
• Quote: “That’s why Survivor’s so tough… They had to lose that game in a million different ways for you to lose that Survivor bet.” — Simon [06:00]

Final Contest Picks Discussion

1. Houston Texans (+3.5) vs. Baltimore Ravens [06:33–07:30]

• Line moved sharply throughout the week due to injury news; hosts locked the Texans in at +3.5.
• Confidence reinforced by Simon’s early-week prediction regarding Lamar Jackson’s status.
• Quote: “Yep. Lock it in. That’s a quick one. Three and a half. Gotta take it for Houston.” — Simon [07:27]

2. New York Giants at New Orleans Saints (-1.5) [07:30–09:20]

• Saints discussed as a potential pick but both hosts express increasing apprehension.
• Noted line has flipped, a “catch a falling knife” scenario common in betting.
• Quote: “I’m leaking confidence as the week goes along because it is the Saints… I thought it would be more love for this Giants side… most guys I’ve talked to just seem like they’re on the Saints with us.” — Simon [08:21]
• Ultimately, this pick is set aside in favor of stronger plays.

3. Dallas Cowboys at New York Jets (+2.5) [09:20–11:18]

• The “brass balls” bet of the week—deeply uncomfortable, high contrarian value, with sharps on the Jets and public on the Cowboys.
• Game is a classic “pros vs. Joes” matchup.
• Quote: “Every pro I’ve talked to is right there with us, but... every public guy I’ve talked to is on the Cowboys. So, yeah, this is pros versus Joes. Good number, good spot.” — Simon [10:32]
• Chad and Simon would still advise Jets at +1.5 but warn against lower.

4. Kansas City Chiefs at Jacksonville Jaguars (+3.5) [11:18–13:33]

• Chad loves this pick; Simon is less certain but notes sharp money aligns with the Jags.
• Debate over contest pride vs. collective goal to finish above .500.
• Simon says, “If you believe in it, you should take a stand on. It’s your favorite bet of the week.” [12:54]
• The Jags are ultimately included in the final five after deliberation.

5. Denver Broncos (+4.5) at Philadelphia Eagles [18:58–20:54]

• Labeled the “Rock and a Hard Place, Hard Rock Bet of the Week.”
• Both hosts like Broncos as undervalued, facing a “lucky” Eagles team.
• Some wariness around line volatility, but four and a half is seen as solid value.
• Quote: “What are we missing here? So I’m like, yeah, I wish I had someone else here that could talk me out of it. But I like the four and a half.” — Simon [19:58]

6. Washington Commanders (+2.5) at LA Chargers [20:54–24:29]

• Simon calls out the line’s holding pattern at 2.5 despite public Chargers money and injury clusters.
• Both hosts recognize the risk in backing an unproven Commanders’ side, but injury attrition for LA is decisive.
• “I would still play it… if I had to take this over the Saints, I would.” — Simon [23:52]

Final Deliberations [24:16–26:29]

• Saints are removed from consideration due to waning confidence.
• Between Broncos and Commanders, Commanders are chosen (“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.” — Chad [25:53])
• Emphasis on not ignoring the value of the number (“let’s not discount the number... the number is a big deal” — Chad [26:12])

Final Contest Card [26:29–26:53]

Locked-in Picks:

1. Rams (already lost)
2. Texans +3.5 (line has now moved, but the pick was locked at +3.5)
3. Jets +2.5
4. Jaguars +3.5
5. Commanders +2.5 (note: +3 available for non-contest bettors)

Notable Quotes & Memorable Moments

• Simon, on betting psychology:
  “At the end of the day, madness and randomness. That’s why we love what we do.” [06:00]
• Chad, on the contest mindset:
  “The only pride I get from the contest is finishing with a winning week. I don’t care if it’s a pick you made that I was against... I just want to finish with a winning week.” [12:33]
• On decision paralysis:
  “I wish I had someone else here that could talk me out of it. But I like the four and a half.” — Simon (on Broncos) [19:58]
• On betting with conviction:
  “If you believe in it, you should take a stand on. It’s your favorite bet of the week.” — Simon (on Chad’s Jags pick) [12:54]
• On the “brass balls” Jets pick:
  “You will suffer for 60 minutes watching this game.” — Chad [09:20]

Timestamps for Important Segments

• 02:27 – Show begins, hosts share personal sports stories
• 04:00 – Free Sharper Square NFL Pick ’Em Contest announcement
• 06:00 – Thursday night Rams loss/takeaways
• 07:30 – Quick lock: Texans at +3.5
• 08:21 – Discussion: Saints vs. Giants apprehension
• 09:20 – Brass Balls Bet: Jets at +2.5 vs. Cowboys
• 11:18 – Chiefs–Jaguars debate (picking the Jags)
• 18:58 – Broncos–Eagles as “Rock and a Hard Place” bet
• 20:54 – Case for the Commanders vs. Chargers
• 24:16 – Deliberations, Saints dropped, Commanders/Denver debate
• 26:29 – Final card review and wrap-up

Tone and Style

The episode is collegial, frank, self-deprecating, and driven by analytical rigor but sprinkled with humor and humility about the randomness of sports betting. The hosts freely admit their doubts, highlight the importance of “the number,” and blend sharp insights with the camaraderie of friends sweating bets together.

Summary for Non-Listeners

This episode is a full walk-through of Week 5 NFL picks from two seasoned bettors, including emotional ups and downs, detailed analysis of line movement and injury news, and candid strategy talk about managing contest entries. The hosts help listeners distinguish between sharp and square plays in the context of ever-shifting odds, ultimately providing a card of four picks (after an early Rams loss) with a “bet like a pro” mindset. If you want to understand the week’s sharp action, get actionable advice, and hear honest bet-sweat banter, this episode delivers.