Sharp or Square – Sweet 16 March Madness Betting Preview: College Basketball Picks & Predictions

Podcast: Sharp or Square (iHeartPodcasts and The Volume)
Hosts: Chad Millman & Simon Hunter
Guest: Joshua Nunn (aka Doc), College Basketball Betting Expert
Date: March 26, 2026

Episode Overview

In this Sweet 16 edition, Chad, Simon, and guest betting expert “Doc” (Joshua Nunn) break down the state of March Madness, analyze the notable dominance of favorites this year, and provide sharp, actionable betting picks for every Sweet 16 game. They discuss how the transfer portal, NIL, and shifting recruiting strategies are reshaping college hoops, and why true Cinderella stories are becoming endangered. The team shares their best bets, “Simon Says” moneyline plays, and the “Brass Balls Bet of the Week”, tackling everything from upset candidates to coaching risers and futures markets.

Main Themes & Analysis

Tournament Trends: Where Have the Upsets Gone?

[02:54–07:19, 08:25–09:34]

• Favorites have dominated: The consensus among the hosts is that the NCAA Tournament has become chalky, with blue bloods and high-seed teams largely advancing.
  • "The nil, it’s killed what I loved — Cinderella stories." – Simon [02:54]
  • Doc: “A lot of the underdogs that we liked hung in there for 35 minutes and then faded in the last five. Didn’t see as many upsets... The rich get richer, and a lot of mid and low majors get their talent plucked each year.” [08:25]
• Why is it happening?
  • Transfer portal/NIL means veteran, stronger players at power programs.
  • Bigger schools can poach mid-major talent; one-bid league teams struggle to keep rosters together.
  • "You really do notice the athletic difference...these good teams just flip a switch in the final five minutes." – Simon [04:51]
• Coaching matters more: Old strategies — stacking 5-star freshmen — are out; building with grown men from the portal/pro ranks is in.

Sweet 16 Betting Landscape

[13:00–16:32, 17:49–19:33]

• Doc: Fewer and fewer true Cinderellas.
  • “High Point did incredible… but you wish we were seeing a team like that in the Sweet 16.” [13:00]
  • “Iowa becomes a Cinderella team… Texas is not a Cinderella in my opinion… they have a huge athletic budget.” [15:50]
• Favorites’ streak by the numbers:
  • Favorites went undefeated for the first time since 1992; best start ATS since 2008.
  • Only six outright upsets by underdogs of 6+ points in last two years before Sweet 16 [10:52].
• Chalk or Dogs?:
  • “We gotta switch...the favorite moneyline round robins might be the move going forward. It’s a cash cow we’re missing out on… just because we’re so adhered to betting these dogs.” – Simon [16:32]

Deep-Dive: Coaches, Futures, and Market Angles

Futures Value & Final Four Paths

[17:49–19:33]

• Who can still offer value?:
  • Houston: “Path is clear… Their defense will provide unique challenges for Illinois, and if they reach the Final Four, any of the four can win.” – Doc [17:49]
  • Purdue: “Starting to come on… can win games and potentially defeat Arizona.” – Doc [18:29]
• Coach Stock Watch:
  • Flynn Clayman (High Point): “Absolutely on the map. Within a year-and-a-half, Flynn Clayman will have a high-profile job.” – Doc [20:14]
  • Big-name mid-major coaches quick to get hired; “You kind of outgrow your pond” – Doc [21:54]
  • “If I was paid millions at High Point? Maybe I’d just stick it out there and always be a 1 or 2 in your league…” – Doc [22:25]

System Schools, Conference Power

[21:54–24:16]

• Arizona State hiring Randy Bennett (from St. Mary’s): Seen as a shrewd “Signetti playbook” move — proven system coach gets a bigger budget and recruiting platform [23:21].
• Big Ten as the monster: Most teams left in the field, driving quality and Cinderella debate [32:14].

Sharp Bets & Key Game Breakdowns

Thursday Sweet 16 Bets

[25:07–27:16]

• Purdue -6.5 vs Texas (Doc):
  • “Texas is just a bit over their skis…they beat BYU and Gonzaga, both banged up. Purdue’s offense is so efficient, they’ll torch Texas’s defense.” – Doc [25:28]
• Simon Says Pick:
  • Iowa +110 ML vs Nebraska
    • “Iowa couldn’t be knocked out by Florida… already beat Nebraska this year. We love those short dogs.” – Simon [26:48]

Friday Sweet 16 Bets

[33:09–36:24]

• St. John’s/Duke UNDER 142.5 (Doc):
  • “Don’t disregard a Rick Pitino team with time to draw up a defensive scheme… Both teams throttle tempo down, defense rules, won’t be enough possessions. My best bet here is under 142.5.” – Doc [33:09]
• Tennessee +4.5 (Doc, conditional):
  • “Without Joshua Jefferson, Iowa State will really struggle with Tennessee on the glass… If Jefferson doesn’t play, I like Tennessee to potentially win outright.” – Doc [35:00]
• Brass Balls Bet of the Week:
  • Tennessee +155 ML vs Iowa State
    • Going out on a limb that Jefferson stays out; Volunteers are “the brass balls bet of the week.” [36:24]

Other Upset & Exotic Bets

[37:28–39:34]

• Potential upsets:
  • “If Alabama makes 19 threes, they can beat anybody… Michigan State-UConn will be a really great game… Illinois could upset Houston, Arkansas could put a scare into Arizona. I’d be stunned if Purdue lost though.” – Doc [37:28]
  • Exotic market: Bet on 3+ seed upsets (over 2.5) in the Sweet 16, found at +113 to +117. [39:00]

Notable Quotes & Moments

• “You really do notice that athletic difference and just the next level these top teams go to in the final five minutes.” – Simon [04:51]
• “It’s hard; you’re not getting that kid from the plucky school who for three weeks in March becomes a heroic story.” – Chad [03:30]
• “I think Houston has a real great shot to get to the Final Four. And then, once you get to the Final Four, any of the four teams that advance to that point are capable of winning the whole thing.” – Doc [18:14]
• “Thursday, give us your pick. Duck got me fired up about Iowa... I’m going to run it back this week with Iowa. Give me Iowa +110.” – Simon [26:48]
• “Our brass balls bet of the week is Tennessee +155 vs Iowa State—going out on a limb that Jefferson isn’t playing.” – Chad [36:37]
• “My best bet for Friday’s St. John’s-Duke is under 142.5.” – Doc [33:09]

Timestamps for Major Segments

• Upsets & State of the Tournament: 02:54–09:34
• Why Favorites are Dominating: 10:52–13:00
• Cinderella Breakdown (High Point, Iowa, Texas): 13:00–16:32
• Best Futures Markets & Coaches: 17:49–21:54
• Thursday Sweet 16 Bets: 25:07–27:16
• Friday Best Bets: 33:09–36:24
• Brass Balls, Upsets & Market Exotics: 36:32–39:34
• Recap and Closing: 39:34–40:22

Final Recap of Picks & Predictions

• Thursday
  • Purdue -6.5 vs Texas (Doc)
  • Iowa +110 ML vs Nebraska (Simon Says)
• Friday
  • St. John’s/Duke UNDER 142.5 (Doc)
  • Tennessee +155 ML vs Iowa State (Brass Balls bet, based on Jefferson’s injury)
• Potential Upsets/Exotics:
  • At least three higher seeded teams winning in Sweet 16 (+113 to +117)

Tone Snapshot

High-energy, sharp-witted, and loaded with actionable analysis, the episode blends entertaining banter (“You sound 100 years old… back in my day, let me tell you about George Mason!” – Chad [05:51]) with deep wisdom for bettors. Both the nitty-gritty of the tournament’s evolution and the specifics of the betting market are unpacked with humor, stats, and sharp takes.

For more detailed picks, in-depth segment analysis, and future market advice, subscribe and rate Sharp or Square wherever you get your podcasts.