Gambling With an Edge

Bob and Richard sit down with Gary Kondler to talk about taxes for gamblers after the big beautiful bill.  It may not be as bad for some of us as we all thought. Spoiler alert - but some gamblers are just screwed.Show Notes[00:00]  Introduction of gambling tax expert Gary Kondler from Kondler & Associates[01:36]  W2Gs under the new tax law[05:24]  Reconciling W2s with session win/loss[09:43]  An example of casino gambling profit and discussion of similar case law[18:04]  Sports betting example[20:46]  Could a day of betting across different sportsbooks be considered a single session?[24:28]  Arbitrage bettors versus poker players [27:06]  What type of gambler would benefit from creating an S corp[30:00]  Casino generated win/loss statements[31:54]  Should clients file on time or file an extension?[37:49]  IRS layoffs [40:57]  How can listeners contact Gary?[42:45]  Brian Camp’s legal opinion[44:55]  Kalshi and other predictive markets[47:48]  Professional versus non-professional gambler[51:34]  Does filing with losses affect the professional gambler classification?Links:Kondlercpa.comhttps://www.taxnotes.com/special-reports/gains-and-losses/taxation-gambling-after-obbba/2025/08/14/7sxhn

Today I speak with Norm Beck, a professional bridge player, magician, and friend about a bet he won, that turned out to be a big loser.Show Notes[00:00] Introduction of Norm Beck, bridge player and magician[00:37]  Norm’s biggest gamble[06:40]  Clever pre-surgery research strategy[13:07]  Hiring another doctor to translate information to family[14:49]  Getting into the gambling business[20:30]  Booking action on random events[23:28]  A billion dollar bet[31:23]  $500k bet on changing a tire [33:45]  “Win Your Line of Credit” blackjack tournament[41:21]  How to contact the show

Buzz Marconi moved to Las Vegas in the 1960s, and somehow transformed from an Italian kid from the south side of Chicago into Cowboy Buzz. It's a wild story.  Check it out.Show Notes[00:00]  Introduction on of Cowboy Buzz[02:07]  Moving to Las Vegas, working at The Stardust[20:53]  Brilliant mob casino strategies[23;10]  Tony Spilotro and Frank "Lefty" Rosenthal[27:19]  Becoming a shift boss Foxy's Firehouse[29:28]  Did certain dealers cheat players?[31:06]  A wild craps swing on credit and Milton Jaffe[35:20]  Milton Jaffe magic trick[37:06]  Opening a restaurant in Las Vegas[41:09]  Stories about dealers, cheating, and work ethic[46:59]  Cowboy Buzz's juice is revealed[48:51]  Naked women tanning at The Tropicana pool[55:53]  Becoming "Cowboy Buzz"[1:02:07]  Playing rugby age 73[1:04:51]  Meeting Max Rubin[1:09:05]  The first Blackjack Ball[1:10:30]  Being a clown diver at Caesars Palace

Bob is off playing the secret game, so I get together with Max Rubin, and Colin Jones to discuss the 2025 Blackjack Ball.Show Notes[00:00] Introduction of Max Rubin and Colin Jones to discuss The Blackjack Ball[00:45] Colin’s induction into The Blackjack Hall of Fame[01:26] Changes to voting for The Hall of Fame and BJ Traveler discussion[06:55] Costume party and best costume [13:20] Ed Thorp[14:49] UCLA Gambling Studies Program [20:13] Card counting competition[24:49] Quiz and final table games (cutting and sequencing) [36:03] Evolution of The Blackjack Ball[40:23] Other highlights from this year’s Blackjack Ball Links:Interview with BJ Traveller https://youtu.be/mnQmlrxApcEUCLA Gambling Studies Program https://uclagamblingprogram.org

Jon Rogers was an old-school bookie.  He started booking baseball with his classmates in 6th grade, graduated to parlay cards in high school, and went pro after high school.  He lived, and booked through a seismic change in the bookmaking industry.  He went from the old days of taking bets over the phone, writing on slips of paper, to moving offshore, and the rise of internet betting.Show Notes[00:00]  Introduction of bookmaker Jon Rogers of Carib Sports[00:59]  Jon’s childhood and early gambling experiences[03:52]  Booking parlays in high school and lottery numbers[08:46]  State lotteries broadcast drawings[11:11]  Kickbacks and paying for protection[13:06]  Super Bowl 1990 FBI raid[16:52]  Charges, recordings, taxes, and going to Vegas[21:37]  Antigua tax laws, bookmaking on paper, then with software[29:28]  1990 case ends[32:32]  Continuing operations in Antigua, accepting credit cards, betting volume, and margins.[35:02]  2003 raid, The Patriot Act[46:42]  The SAFE Port Act and closing down[48:44]  Life after bookmaking, settling the case, and living happily ever after