Sharp or Square – Milan Cortina Winter Games Update

Podcast: Sharp or Square (iHeartPodcasts and The Volume)
Episode Title: Milan Cortina Winter Games Update - Curling, USA Hockey, Eileen Gu and More
Date: February 19, 2026
Hosts: Chad Millman & Simon Hunter
Guest: Matt Mitchell

Episode Overview

This special Olympic-themed episode dives into the betting angles, biggest narratives, and memorable moments from the 2026 Milan Cortina Winter Games. Host Chad Millman, pro gambler Simon Hunter, and frequent guest Matt Mitchell go beyond the odds to discuss the most exciting, controversial, and even bizarre stories from these Olympics, including USA Hockey's performances, a curling scandal, Eileen Gu’s representation of China, and the colorful off-ice/field drama capturing global attention.

Key Discussion Points & Insights

1. The Olympics Are Not Traditionally a Betting Hotspot

• Simon Hunter: "The truth is, Olympics is not a big betting sport...Winter Olympics especially is not a big betting sport. But I will say that these Olympics have captured people's attention because there are so many freaking narratives." (04:38)
• The trio agrees that compelling storylines, not lines, are making these Games a must-watch—even for seasoned bettors.

2. Olympic Hockey Betting: Women's & Men's Stories

• Matt Mitchell: Raves about the endless action of Olympic hockey, especially the women’s tournament. The US women's team is dominant and stacked with talent, making them favorites, but such heavily favored lines are tricky for betting.
  • "These American ladies are a collection of complete savages and I really look forward to watching them in the gold medal match..." (05:52)
• Simon Hunter: The unpredictability of men's hockey (team chemistry, “hockey bros” vibe) provides interesting betting angles, with USA men showing surprising cohesion.
  • "You could tell this USA team gels... You're looking for that stuff as someone that's betting, looking for angles and it’s shown up." (09:39)

3. Off-Ice Olympic Village Shenanigans: Condom “Shortage”

• Olympic narrative: News broke that 10,000 Olympic condoms had "run out."
• Simon Hunter & Chad Millman: Point out that many athletes grabbed them as souvenirs, for resale, not just for fun.
  • "They put the...condom with the Olympic symbol on" (11:14, Chad Millman)
  • "That's a money maker." (11:21, Chad Millman)

4. Curling Controversy: "Cheating" Canadians & Swedish Sting

• Chad Millman & Simon Hunter: Canada, usually seen as polite, is in the hot seat after Swedes set up their own camera to prove a suspected foul (illegal “double touch” past the hog line) in curling.
• Matt Mitchell:
  • "The culture of curling is one of incredible sportsmanship and self regulation...The Swedes believed the Canadians were cheating and not calling it. So they set up their own camera." (15:39)
  • The scandal had all the elements: a sting, a villain, and high/low stakes.
  • "It's low stakes because it's curling, but it's also high stakes because it's the Olympics. 10 out of 10 scandal." (17:18)

5. Absurd and Absorbing Athlete Drama

• A medalist admits cheating—on his girlfriend, not in sports—during his acceptance speech, generating sensational (and misleading) headlines.
  • Matt Mitchell:
    • "Athlete admits cheating in acceptance speech, which was true and misleading and made everybody click on it..." (18:58)
• Panel laughs at Euro/American culture clashes and tabloid sports narratives.

6. Inspirational Performances: Shiffrin & the “Cross-Country GOAT”

• Simon Hunter: Celebrates Mikaela Shiffrin’s record-setting gold, noting her open discussions of pressure and setbacks.
• Norway’s Johannes Høsflot Klæbo:
  • Dominates cross-country skiing with a new, unmatched technique, moving at six-minute miles up snowy hills.
  • Matt Mitchell:
    • "It was churning like a train...doing so so quickly that it looks like he’s jogging was absolutely the most impressive part of it." (27:38)

7. Eileen Gu, Money, and National Allegiances

• Major media attention on Eileen Gu (San Francisco native, skiing for China), with reports she’s now the 4th highest paid female athlete in the world—her multi-million-dollar deal with China generating controversy.
  • Simon Hunter:
    • "...all the money she has gotten from China, which was a story this week that broke...she has been paid millions of dollars to ski and compete for China." (31:18)
• Chad Millman:
  • Explains that "China basically spent 40 million on just American athletes alone" for these Games (Wall Street Journal report). (32:20)
• Debate: Is it “mercenary” to compete for the highest bidder, or just taking advantage of the system?
  • Chad Millman: “I'd rather be great under the American flag than China's flag. But...the money is just that big...that's an insane, like, what they're reporting is an insane amount of money that she's being paid." (35:34)

Notable Quotes & Memorable Moments

• Simon Hunter (on curling scandal):
  • “Curling has a controversy and it has turned the world against Canada for being foul mouthed and poor sports. That’s amazing to me.” (15:04)
• Matt Mitchell (on curling sportsmanship):
  • "The whole Scandinavian region is so unbelievably calm and refined and within themselves emotionally, I’m none of those things. So seeing the Canadian lose his mind and get really pissy and the Swedes look at them with the same look many executives look to me when I would be explaining something of like, how curious your anger is..." (16:23)
• Chad Millman (on the Olympics' ever-present hookup culture):
  • “So rest assured, people can have safe sex in Milan Cortina right now." (12:36)
• Matt Mitchell (on Olympic betting rituals):
  • "If one more goddamn Korean bullpen blows a seven run lead, I'm not going to live to see this girl's 10th birthday." (07:23)
• Chad Millman (Eileen Gu):
  • "No one knows how real the money is because it is China." (32:20)
• Simon Hunter (on patriotism vs. cash):
  • "At the end of the day, it's not just about being a mercenary...it's about the joy and like draping the flag and walking in the opening ceremonies." (34:17)

Timestamps of Important Segments

• 02:38: Show opens, set-up for Olympic-themed discussion
• 05:52: Olympic hockey betting—US women’s dominance & joy of betting on games
• 11:12: Olympic Village "condom shortage" and souvenir story
• 15:03: Curling controversy: Canadians accused of cheating revealed by Swedish camera "sting"
• 18:30: Athlete admits cheating on girlfriend in acceptance speech—tabloid moment
• 25:55: Mikaela Shiffrin & Klæbo’s cross-country skiing dominance
• 31:18: Eileen Gu, China’s big-money athlete deals, and controversy over national allegiances
• 35:34: Patriotism vs. mercenary motivation: panel debates “what’s your price?”
• 36:49: Outro; reflection on Olympics being a huge conversation starter, even for non-bettors

Tone & Style

Lively, irreverent, and conversational with plenty of humor. The trio balance sharp sports-betting insights with locker-room banter, pop culture references, and genuine awe at both human achievement and absurdity. The episode delivers both entertainment and thoughtful reflection on modern sport.

Listener Takeaways

• Even for career bettors, storylines, scandals, and human drama—not just betting angles—make the Olympics must-watch TV.
• The US women's hockey team is historically dominant, and while they're often heavy favorites, upsets and line movement always lurk in Olympic competition.
• Curling and other niche sports provide fertile ground for drama and unexpected controversy.
• Modern Olympic athletes are often savvy, global professionals—creating new ethical, financial, and national debates.
• The Olympics spark once-in-four-year debates even among football-first sports fans.

This episode is essential listening for sports fans who want the betting world’s take on the biggest (and weirdest) Ice Games moments, distilled with humor and in-depth perspective.