The Herd with Colin Cowherd – "Sharp or Square: FINAL NFL Week 3 bets"

Date: September 21, 2025
Hosts: Chad Millman & Simon Hunter

Episode Overview

This episode of Sharper Square features Chad Millman and professional bettor Simon Hunter as they make their final selections for NFL Week 3, focused on contest entries against the spread. In typical "in-the-room" style, the hosts walk listeners through their thought process, betting rationale, and market moves, covering key matchups: Packers-Browns, Texans-Jaguars, Rams-Eagles, Cowboys-Bears, Broncos-Chargers, and more. The episode leans into dog bets, market insights, contest strategy, and some comic misery about being Bears fans.

Key Discussion Points & Insights

1. State of the Board: Week 3 Context

• Quarterback Injuries: Up to five starters missing, but hosts avoid leaning on those matchups.
  • Simon: "[Week 3] is a known week for dog betters. Like, it's a good week to be betting dogs." (03:08)
• Contest Dynamics: Emphasis on locked-in contest lines vs. live market moves and the challenge of line movements after Wednesday.

2. Game Focus #1: Packers at Browns

• Line: Browns +8.5 in contest (market at +7.5)
• Lean: Strongly on Browns
  • Host rationale: Browns are undervalued, Packers are overhyped after strong public start.
  • Simon notes bookies "are very happy when I come in to bet on Cleveland." (05:13)
  • Defense and variance play factors: "We're on [an] elite, top tier defense at home against an overvalued team versus an undervalued team." – Chad (07:30)

Memorable Segment:

• Chad admits he had to “watch the condensed version of this game on the rowing machine” to stomach betting the Browns (07:11)
• Simon: “[W]e are betting on Joe Flacco... we’re going to need a back door. We’re going to need a miracle cover at some point.” (06:41)

3. Game Focus #2: Texans at Jaguars

• Line: Texans +0.5 (contest), market down from +2.5
• Discussion: Split feelings but ultimately a lean to Texans based on 'buy-low' logic and divisional trends.
  • Simon raises concerns about Houston's run defense but likes the desperation angle and market contrarianism.
  • "I love a desperate team like they are with a type of mentality they have in d’Amico Ryans." – Simon (11:25)
• Contest/Wagering Dilemma: Not thrilled with the contest line but trust historical divisional trends.

4. Game Focus #3: Rams at Eagles

• Line: Eagles -3.5 (contest)
• Insight:
  • Hosts conflict with market sentiment ("against the wise guys").
  • Chad feels like the Eagles "can win at an 80% level and not even open up our full bag of tricks yet." (13:28)
  • Simon highlights the matchup – LA’s O-line weakness versus the Eagles’ pass rush, Stafford’s lack of mobility as a key.
  • "If you can get the three like you kind of hard rock, go get it. But I [have] no issues taking the three and a half." – Simon (16:44)

5. Game Focus #4: Cowboys at Bears

• Line: Bears +1.5 (market), but -1.5 in contest (Bears as favorites)
• Action: Pass in contest due to line value lost; both hosts still personally like the Bears as underdogs but won’t force a bad contest entry.
• Simon: "I can't get over how much I love the Bears in the spot against a Cowboys team that Dak is going to have stinker games." (24:06)
• Chad (on Bears fandom): "Nobody who's a Bears fan is confident in the Bears ever. We hate the organization, the ownership..." (27:17)
• Weather becomes a potential factor (praying for rain to neutralize Dallas attack).

6. Game Focus #5: Broncos at Chargers

• Line: Broncos +2.5 (contest)
• Position: Taking Denver, citing historical spot/trends against Chargers playing third straight divisional game.
  • Simon: "This is an incredibly, incredibly important game. It really does feel like it's going to dictate this division..." (31:24)
  • Both like the number, would shop for +3.

7. Other Games Considered

• Jets at Buccaneers (+7.5): Ugly, but contest line makes it appealing due to Bucs' offensive line injury cluster and Jets fitting the “0-2 desperation” trend.
• Panthers (+5.5 vs. Falcons): Professionals betting it, but hosts reluctant to recommend formally.
• Saints at Seahawks, Chiefs-Giants, Lions on MNF: Discussed for line value; ultimately passed due to confidence concerns.
• Patriots-Steelers: Briefly considered with news of Christian Gonzalez injury (Patriots DB).

Final Five Picks (Contest Entries)

Announced at: [39:55–40:32]

1. Cleveland Browns +8.5
2. Houston Texans +0.5
3. Philadelphia Eagles -3.5
4. Denver Broncos +2.5
5. New York Jets +7.5 (against Buccaneers)

"God, this is going to be a miserable day. Miserable or it's going to be the greatest day ever."
— Chad Millman (39:55)

Notable Quotes & Memorable Moments

• Simon (on contest betting):
  "There's some games that one of us can talk about the other person out of...as soon as I saw the number, I said, there's no way we don't take this number..." (04:52)
• Chad (on Bears):
  "We need the rain like a farmer needed rain during the Dust Bowl." (28:13)
• Simon (on ugly bets):
  "Gross. One. Hold your nose. Take it." (31:24)
• Chad (on Sunday morning optimism):
  "That's the beauty of Sunday mornings in the fall." (40:32)

Timestamps for Key Segments

• [03:05] — Week 3 overview & injury context
• [04:52] — Packers at Browns deep dive
• [08:18] — Texans at Jaguars market analysis
• [12:47] — Rams at Eagles debate
• [23:06] — Cowboys at Bears, contest line pass
• [28:47] — Broncos at Chargers, deep trends
• [34:33] — Jets as a contest play
• [39:55] — Final five contest bets revealed

Tone & Style

• The hosts maintain a conversational, insider tone, with playful banter and mutual ribbing.
• Transparency about uncertainties and contest frustrations powers much of the episode.
• Their analytical approach is backed by insights on line movement, market splits, and historical context, with strong awareness of contest versus sportsbook differences.
• Bears and Jets fan misery adds self-deprecating humor throughout.

Summary for Listeners

This episode is perfect for NFL bettors and contestants looking to understand high-level contest strategies, late-week line value, and the psychology behind tough decisions. Chad and Simon walk listeners through their honest debates and draw sharp lines between personal bets and smart contest entries, capping with their final five picks—anchored by ugly dogs and a dose of hope for Sunday glory.