Oprah Winfrey gave 276 people brand-new cars on live television. Some later discovered they could owe up to $7,000 in taxes just to keep their “free” gift. In September 2004, Oprah opened the 19th season of her show with an enormous surprise. Her producers had filled the audience with people who genuinely needed transportation. Each was about to receive a Pontiac G6 worth roughly $28,500. First, Oprah brought 11 people onto the stage and gave them cars. Then she handed gift boxes to everyone else, telling them that one box contained the keys to another vehicle. Every box had keys. The audience screamed, cried and hugged strangers as Oprah announced that everybody was getting a car. The entire giveaway was worth more than $7 million. But the cars hadn't come out of Oprah's pocket. Pontiac supplied them as part of a massive promotional campaign. And there was something the cameras hadn't explained. Under US tax rules, the cars counted as prize income. Pontiac covered sales taxes and certain local fees, but winners remained responsible for income taxes. Depending on their tax brackets, some faced bills approaching $7,000. They could pay the tax, sell the car to cover it, or decline the prize. One recipient described the situation as getting a car at a 75% discount rather than receiving one for free. The gift was still valuable. But some of the people chosen precisely because they needed financial help now had to find thousands of dollars they hadn't planned to spend. Two months later, Oprah held another giveaway. This time, the gifts came with checks intended to help recipients pay their taxes. Twenty-two years later, millions still remember Oprah shouting that everybody was getting a car. Far fewer remember the bills that arrived afterward.