The Herd with Colin Cowherd – Sharp or Square: March Madness Betting Preview (March 18, 2026)

Episode Overview

This episode of Sharp or Square, hosted by Chad Millman and pro bettor Simon Hunter, delivers a comprehensive NCAA March Madness betting preview. Special guest Josh Nunn, aka "Duck" (co-host of the Big Bets on Campus podcast and college hoops sharp), joins to offer expert picks, bracket strategies, and actionable insights on upsets, seed math, betting value, and stand-out players. The episode leans into real talk for both recreational and sharp bettors, focusing on data-driven predictions, an honest assessment of the bracket landscape, and a little bit of college basketball nostalgia.

Key Discussion Points & Insights

1. March Madness Betting Landscape in 2026

• Value of Classic Upset Seeds: Duck notes that the gap between top and bottom seeds is larger than ever due to NIL and the transfer portal, warning bettors not to overvalue the famous 12-5 or 13-4 upsets this year (08:43).
  • "The gap between the 1 through 4 seeds and the 13 through 16 seeds has never been wider... I don't see a lot this year with any of the 12 through 16 seeds." – Josh Nunn (08:43)
• Where to Find Real Upset Value: Focus on 11-seeds like VCU or South Florida, which are stronger than usual and have favorable matchups. The 12-seeds in particular (like High Point, McNeese State) have poor draws this year.

2. Play-In Games: Best Bets and Leans

• SMU -6.5 over Miami (OH) is Duck’s best play for the First Four (12:23).
  • Miami (OH) “could get overwhelmed a bit here by the athleticism of SMU. ...SMU took Duke to the wire at Cameron Indoor. They defeated Louisville, North Carolina, Texas A&M.” – Josh Nunn (12:23)
  • Miami (OH) is correctly seeded, but likely out-classed.

3. Bracket Strategy: Don’t Get Too Cute with Upsets

• Advice Against Overloading Brackets with Upsets: Duck urges caution against chasing Cinderella runs for the sake of being clever (25:54):
  • “The gap between seeds one through four and say 13 through 16 is wider than it’s ever been... But I do think there’s value in the 11 line.” – Josh Nunn (25:54)
• Best Spots to Hunt for an Upset: 11-seeds like VCU and South Florida are real upset candidates (09:30, 25:54).

4. Futures Market & Top Seeds

• Odds and Paths of Favorites: Duke (+275), Arizona, Michigan (+350), Florida (+650), Houston (+900) are the five teams under 10:1 to win it all.

  • Simon notes that Duke is often hated, but the brand "has its haters and it should...50 years of just people hating that brand" (15:29).
  • Discusses how John Shire leading Duke is changing perceptions, but the anti-Duke sentiment lingers.

• Duke’s Real Chances: Duck is bullish on Duke, noting health, depth, and the dominance of Boozer, but warns the odds may not be worth it (17:02).

  • “Boozer can live at the line ...Duke’s really buttoned up and they’re going to be tough to beat.” – Josh Nunn (18:12)

• Outsider Watch: Names like Dominic Davis at Cal Baptist and Acuff at Arkansas are highlighted as potential unsung heroes who could catch fire (18:41).

Notable Quotes & Memorable Moments

“The gap between the 1 through 4 seeds and the 13 through 16 seeds has never been wider.”
– Josh Nunn (Duck), 08:43

“Simon, as an off-season bettor who now just counts your gold bars and calculates the cost and value of your Pokemon cards, how are you going to celebrate this week?”
– Chad Millman (07:09)

"They've been using some of the NIL techniques long before NIL was even a thing. So it's a disadvantage now because everybody else is now able to do it."
– Josh Nunn (20:30), on coaches like John Calipari and Sampson

“Simon says: I’m definitely betting Wisconsin minus ten...If they have their A plus game, they could easily win this game by 20.”
– Simon Hunter (39:21)

Best Bets and Actionable Advice

Thursday’s Top Plays

• Wisconsin Team Total Over 87.5 (20:59; 39:21)

  • “Wisconsin should approach 100 points here.” – Josh Nunn

• Duke-Siena Under 136.5 (22:06)

  • Siena only plays six guys and lives in the mid-range; expect a low-possession, grind-it-out game.
  • Duck’s projected score: Duke 78 – Siena 52.
  • “I like the under at 136.5. Siena's offense is really, really going to struggle.” – Josh Nunn (22:06)

• Idaho-Houston Under 136.5 (23:58)

  • “Full game Idaho Houston under 136 and a half.” – Josh Nunn (23:58)
  • Houston’s defense, both teams’ slow pace should keep scoring suppressed.

Friday’s Top Plays

• LIU-Arizona Under 152 (32:51)
  • “This is a dead nut under 152. LIU is going to struggle mightily to score...Arizona is unlikely to put up more than 80 to 85.” – Josh Nunn (32:51)
• Wright State Team Total Under 63.5 vs. Virginia (35:06)
  • Wright State attacks the rim, but Virginia's block shots and defense should bottle them up.
• Cal Baptist-Kansas Under 138 (36:21)
  • “Kansas has to travel all the way across the country...Cal Baptist plays sound defense...I like the under.” – Josh Nunn (36:21)

Upset Watches / Bracket Angles

• Best Upset Candidates:

  • Actionable: Watch the 11-seeds: VCU and South Florida are Duck’s top Thursday upset possibilities.
  • Longshot: Keep an eye on Cal Baptist due to travel, matchup, and a possible standout performance from Dominic Davis (18:41, 36:21).
    • “Dominic Davis can score 40 points at any time...” – Josh Nunn

• Bracket Props:

  • Sum of Final Four Seeds – Under 9.5 (37:26)
    • “I have an exotic bet that I really like here ...total, some seeds to make the Final Four ...under nine and a half.” – Josh Nunn (37:26)
  • WCC Schools (Gonzaga, St. Mary’s, Santa Clara) – Over 3.5 tournament wins (38:38)

Final Four & Champion Lean

• Duck hesitates to lock in picks but expects a chalk-heavy Final Four (lots of 1- and 2-seeds).
• Suggests overachieving WCC teams, Gonzaga leading the way, for a prop bet.

Top Segment Timestamps

• [02:03] – Show introduction, guest intro
• [08:18] – Duck’s myth-busting on seeding, true upset value
• [11:34] – Play-in games best bet: SMU -6.5 vs. Miami (OH)
• [15:27] – Examining public perception and value of Duke futures
• [17:02] – Duck’s take on futures: top teams, why value is mostly gone
• [20:59] – Thursday’s actionable bets (Wisconsin, Duke-Siena under, Idaho-Houston under)
• [25:54] – Bracket strategy: Don’t get upset-happy; where upsets could actually happen
• [32:51] – Friday’s best bets: LIU-Arizona under, Wright State under vs. Virginia, Cal Baptist-Kansas under
• [37:26] – Final Four predictions, prop angles (sum of seeds, WCC wins)
• [39:19] – Simon says: Wisconsin -10/-9.5
• [40:16] – Brass Balls Bet of the Week: TCU +120 over Ohio State

Segment: “Simon Says” & “Brass Balls Bet of the Week”

Simon Says:

• “Wisconsin minus 10. Minus 10.5 at Hard Rock. Now minus 9.5. …If they have their A plus game, they could easily win this game by 20.” – Simon Hunter (39:21)

Brass Balls Bet:

• TCU +120 vs. Ohio State (Moneyline) (40:16)
  • Supported by Duck: “TCU...got hot down the stretch in Big 12 play…took Houston to the wire. I think TCU is a strong team and a team that I have also picked to advance out of the first round.” – Josh Nunn (40:36)

Overall Tone & Takeaways

The show is fast-paced, candid, and deeply analytical – balancing humor and nostalgia (sharing sentimental stories, ragging on Duke, references to Rod Strickland’s Blue Demons roots) with sharp, practical advice. Chad and Simon play off Duck’s encyclopedic knowledge for insights fans and bettors couldn’t get elsewhere.

Best for: Any listener looking for actionable, data-driven March Madness advice—especially those filling out a bracket, hunting for value, or curious about why classic upset narratives may not pay off in 2026.

Quick Hits

• Don’t overload your bracket with upsets this year—stick to the reliable 1- to 4-seeds, but use 11-seed value when hunting for that needed “contrarian” punch.
• Target the under in matchups with mid-majors whose style drags down pace, especially against elite, defensively stout teams.
• Props & futures are more about novelty/exotics than serious edge at this stage; the best betting windows for favorites are mostly gone.
• Duke, Wisconsin, Houston: all strong tournament picks, but know your price before pressing the bet.
• Brass Balls: root for TCU to surprise in round one.

“It’s all about the next bet and the next series of events that are happening. ...I try to look forward to what’s happening next so we can get people to the window.”
– Josh Nunn (Duck), 05:51