Tosh Show | "My Chess Grandmaster - Sam Shankland"

Host: Daniel Tosh
Guest: Sam Shankland (Chess Grandmaster)
Date: January 20, 2026

Episode Overview

This episode explores the mind and career of Sam Shankland, one of the top American chess grandmasters. With comedian Daniel Tosh at the helm, the conversation bounces between chess culture, competitive pressures, personal stories, and smart, irreverent humor. From childhood interests to global chess circuits, and from competitive fall-offs to pot-laced cookies, Tosh invites listeners into the world behind the chessboard—while always keeping it light, witty, and surprisingly heartfelt.

Key Discussion Points & Insights

1. Early Life and the Accidental Chess Prodigy

• Growing Up in Orinda, CA:
  • Sam describes his suburban roots, the quirky fake-Spanish naming in California, and attending the Berkeley Chess School ([10:00–10:25]).
• Sports vs. Chess:
  • Loved sports, ranked 5th out of 60 boys athletically as a kid, but a baseball accident redirected him ([10:46–11:44]).
  • “If that guy had not drilled me in the face, I don’t know if I’d be US Chess Champion.” – Sam ([11:31])
• Chess Discovery:
  • Learned the game from his dad at 6, got hooked after beating the school’s top player at 9 ([13:14]).
  • Notoriously forced rule changes in afterschool chess for too-frequent pizza-party victories ([13:30–14:08]).

2. Family, Priorities, and Support

• Parental Support:
  • Parents were “very supportive” though priorities sometimes clashed.
  • Took a gap year; gold medals “gave them a lot to brag about” ([14:08–14:34]).
• Sibling Dynamics:
  • Has a younger brother who doesn’t play chess; “chess is the only game I’m really good at,” admits Sam ([14:50–15:01]).

3. Chess, Poker, Games and Competitiveness

• Poker vs. Chess:
  • Sam prefers chess’s fairness to poker’s luck: “In poker, I can just totally play better than you all day long and still lose” ([15:04–15:37]).
• College & Chess Choices:
  • Prioritized chess over school when invited to the US Olympic Chess Team, but did finish his degree ([16:13–17:06]).
• Travel:
  • Travels ~130 nights a year; enjoyed more as a young player ([17:59–18:04]).
  • Recent trips: “St. Louis, Thailand, India, and London” ([18:14–18:50]).

4. Chess Professionalism & Training

• Daily Practice:
  • Rarely goes a day without some chess, except a TV show jungle stint ([19:47–20:23]).
• Preference for Over-the-Board:
  • Trained “classically,” calculates best on 3D boards, struggles with online formats ([20:54–21:39]).
• Drug Testing in Chess:
  • Yes, subject to Olympic-level rules. “If I had tested positive for steroids, I would have been kicked out” ([21:40–22:26]).
• ‘Drug Phase’ Stories:
  • Brief, comical weed encounters, including accidentally eating two edibles at his mom’s party ([22:33–23:20]).

5. The Culture and Conduct of Chess

• Board Game or Sport?:
  • "It’s a game that has a board… but I also consider it a sport." ([23:35–23:40])
• Code of Conduct:
  • Both formal and informal rules; bad actors can be banned or just uninvited ([23:54–24:44]).
  • Humorous aside on foot-touching under the table ([24:59–25:29]).
• Calculation Depth:
  • “In a linear position, as many [moves] as I want — 20, 40, whatever. But in a complex one… If I can calculate four [full] moves ahead, that’s huge” ([25:33–25:56]).

6. Chess History and Gender Dynamics

• Greatest of All Time Discussion:
  • "Greatest" vs. "Best"—Magnus Carlsen is best, but Kasparov “inspired me the most” ([26:05–28:44]).
  • “Every generation’s athletes are better than those who came before.”
• Age and Decline:
  • Peak is typically mid-20s to early-30s. "When we won the Olympiad, I was 24… I was the second oldest" ([30:03–30:38]).
• Women in Chess:
  • Praises Judit Polgar, who beat Garry Kasparov, as a “science experiment” of genius raised by design ([31:46–33:13]).
  • Sam beat Polgar in her last professional game: "I did a very big disservice to the world. She doesn’t play anymore. And I beat her in her final game before retirement" ([33:13]).

7. The Business of Chess

• Earnings at the Top:
  • Magnus Carlsen: “Certainly over $10 million… under $100 million” ([41:35]).
  • Top 100: about $60,000/year, “depends where you live” ([41:52–42:20]).
• Books vs. Prizes:
  • “The best-selling book has made me more than winning the US Championship, two Olympic Golds, two World Cup quarterfinals, the Prague Masters, and the Beall Masters combined.” ([44:16]).
• Chess Hustlers:
  • Encounters in Washington Square Park—most locals now recognize him ([46:21–46:45]).

8. Chess Ranks & What It Takes

• Grandmaster Requirements:
  • “The Grandmaster threshold is 2500 and… you have to have three norms… against at least three Grandmasters, five countries, nine games” ([37:40]).
  • Sam firmly denies any KKK involvement, a tongue-in-cheek riff on the elite “grandmaster” title ([37:40–37:55]).
• Skill vs. Talent:
  • Anyone can reach top 1% with total dedication; Grandmaster, “hard no” ([36:00–36:23]).
  • Encourages aspiring players:
    • "Always play for the love of the game. As soon as chess stops being fun, you’re gonna stop improving."
    • "Treat yourself like a top athlete… If you don’t train, nobody’s going to yell at you… You need that self-discipline." ([50:28–51:12])

9. Life, Setbacks, and Motivation

• Career Setback:
  • Sam traces his performance decline to May 2022, after getting COVID-19 ([51:18]).
  • Tosh: “You just need a hype man. I could do some headwork and get you right back to the tip top.” Sam: “Not possible.” ([52:16–52:30])
• Current Team:
  • Has a coach and manager, “all that.” ([52:44])

10. Offbeat Questions and Fun

• Chess Openings:
  • Sam’s not a “London System” regular; English opening “not the GOAT.” ([30:38–31:14])
• Drag-Queen’s Gambit:
  • “F. Marry. Kill.” with Bobby Fischer, IBM Deep Blue, and Queen’s Gambit’s lead—kill Deep Blue! ([42:22–42:54])
• Arm Wrestling Finale:
  • Sam and Daniel arm wrestle for a “draw.” ([53:08–53:39])

Notable Quotes & Memorable Moments (with Timestamps)

• On Luck vs. Skill in Games:
  “In poker, I can just totally play better than you all day long and still lose… In chess, if you play better, you win.” – Sam ([15:04–15:37])

• On Chess vs. Sports Ages:
  “You look at the top rating of any individual chess player—almost always between 25 and 30.” – Sam ([52:50])

• On Magnus Carlsen:
  “I think he’ll retire at number one in the world. I don’t think he’s going to be number two when he retires.” – Sam ([41:08])

• On Greatest of All Time:
  “In sport, every generation of athlete is always better than the one that came before it… All this nostalgia around Babe Ruth… You didn’t even play with Black people, come on.” – Sam ([26:57])

• On Judit Polgar:
  “She got to like number 7 or 8 in the world… but she doesn’t play anymore. And I beat her in her final game before retirement.” – Sam ([33:13])

• Advice to Aspiring Chess Players:
  “Always play for the love of the game. As soon as chess stops being fun, you’re gonna stop improving… You need that same dedication as any top athlete.” – Sam ([50:28–51:12])

• On Age and Performance:
  “How much of my fall from grace is just getting older, and how much is Covid? You could clearly see, that’s exactly the point where the graph starts going down.” — Sam ([51:58])

• Tosh’s Humor on Lawn Chess:
  “Anytime I go to a hotel that has lawn chess, I get so excited… My son just grabs the bishop and pretends it’s his large uncircumcised penis and starts chasing his sister around.” – Daniel Tosh ([54:55])

Important Segment Timestamps

• Getting Into Chess: [13:14–14:08]
• Travel Schedules & Locations: [17:59–18:50]
• Drug Testing & Doping in Chess: [21:40–22:26]
• Chess Gender and Judit Polgar: [31:46–33:13]
• The GOAT Debate & Generational Progress: [26:01–28:44]
• Grandmaster Requirements Explained: [37:40]
• Book Earnings Surpassing Titles: [44:16]
• Advice to Aspiring Chess Players: [50:28–51:12]
• Career Setback—The COVID Moment: [51:18]
• Arm Wrestling Draw: [53:08–53:39]

Episode Tone and Style

The episode mixes Daniel Tosh’s signature irreverence and playful questioning with Sam Shankland’s thoughtful, candid insights and dry humor. The balance of intelligent discussion and comedic asides makes this a fun, accessible, and informative listen, whether you know chess or not.

Summary Takeaway

Daniel Tosh sits down with a world-class chess grandmaster and delivers an episode that’s equal parts education, candor, and comedy. If you want to glimpse the world of modern chess—the discipline, the culture, the travel, the weird stories, and the shades of intellectual and personal struggle—this is the episode for you.