AUDIO – YOU BET –
June 25, 2026 – Tim Pughsley built a sports-betting website that moved billions, then the I.R.S. got involved. In the age of FanDuel and DraftKings, where is the line between legal and illegal gambling?According to government figures compiled later, the operation was a two-billion-dollar business. It was, Pughsley told me, “a money-printing machine.” But there was at least one thing that Pughsley seemed to like more than money: the annual Red44 employee conference. The event, which Pughsley called “Christmas in August,” was always held just before the start of the N.F.L. season, and featured seminars on the gambling trade. He summoned his top bookies to attend, and he told them in group chats to come ready to learn—and work. “Let’s get fired up!!” he said in one message. “Anyone have a cell phone stand to tape the meeting?” he asked in another.
