Harding's post-Olympic resume also features a honeymoon sex tape -- and earlier this year, a tell-all memoir called "The Tonya Tapes." None of it has set her up financially but after more than a decade as a post-Olympic punch line, she remains hopeful.
"I look forward to next year, I look forward to tomorrow. Maybe one of these days, I'll make the money off of the punch line as well," Harding said with a laugh.
Yet not every Olympian wants to cash in. Eric Heiden won five speed-skating gold medals at the 1980 Winter Olympics in Lake Placid. But after the Games, he shocked his agent Art Kaminsky by turning down a bundle.
"They were going to offer me, $400,000 a year, for three years, to be on the box of Kellogg's Corn Flakes, and I remember looking over at Art and going, 'I don't want to do this, because I enjoy my private life,'" Heiden said.
Although Heiden recalls that Kaminsky's jaw dropped at his response, he didn't want to promote something he wasn't comfortable with.
Instead, Heiden went to medical school after the Games. He's now a top orthopedic surgeon and serves as the medical director for the U.S. Skate and Cycling Association, but he says it might not have happened in today's climate.
"If I was offered some of the endorsements that the athletes get now, I don't think I probably would be sitting here with M.D. after my name," he said.
That's because the numbers that Phelps' people have been talking about publicly -- $100 million over his career -- are indeed eye-popping.
Former figure skater Tai Babilonia, who was also at the Lake Placid Olympics, says the offers were much simpler when she was an Olympian.
"We were happy to get jewelry. We were happy to get a plaque. There's an innocence that's been lost to me. They've got agents, they have managers, they have publicists, they have this and that and we just had coaches," Babilonia said.
Home-schooled from the seventh grade onward, pairs skater Babilonia surrendered the simple pleasures of high school life in California to prep for Olympic glory in 1980 with skating partner Randy Gardner.
"I didn't know any better. I wanted to train for the Olympics and be in the ice rink. That's where I was happiest," she said. "Still to this day, I'm happiest in the rink."
But when Gardner suffered an injury, their Olympic dreams ended instantly. Three months later, she was on the road in an ice show, dealing with her Olympic hangover, unprepared for the real world.
"I just thought when you're the star of an ice show, everything's gonna be done for you and everything's gonna be laid out, and you just have to skate. And that was furthest from the truth. You're out there on your own," Babilonia said.
Alone and away from home, she would call her mother, whose advice was to just plow through it. Along the way, she beat a late-'80s drug problem and now is engaged to comic David Brenner. Today, like many of her fellow Olympians past, she counsels aspiring Olympians to plan for their future, but not to overdo it.
"I just keep saying pace yourself. People are gonna start tugging at you and wanting you to do this and that and your goal is to train correctly and have no distractions," she said. "You can find a balance. But just don't go Hollywood too quickly."