With the help of his own personal memories and archive footage, Appel tries to understand his dad’s passion for gambling. At the same time he meets Harry Engels whose list of young ex-girlfriends is as endless as that of his stories and jokes. For 30 years he has successfully made a living as a bookie. The director then pays a visit to inmate and notorious swindler Harry Hofland, who has been behind bars for ten years for a wide variety of fraudulent activities. The last of the gamblers is poker enthusiast Ted Stolzenbach, another player the filmmaker masterfully investigates on the way to revealing the psychology of gambling.