When I was a kid I won a trip for 4 people to Washington DC (plane and hotel) plus $500 spending money for the trip from entering a contest I found on the back of a Cheerios box. It was a mail-in entry and I had entirely forgotten about it but weeks later I got a letter saying I won. My parents had no idea I entered and thought it was junk mail at first but were super excited when they realized it was real. Everything went smoothly and we got a fantastic family trip and memory out of it.

A friend of mine got roped into a game show when he was in Japan and ended up winning ~ $50,000 USD after taxes.

I think it was one of those shows where you had to contort your body into particular shapes to fit through a sliding wall.

Anyway, he bought a truck and paid off some of his family’s bills and now he’s running for some sort of city council position, but he’s kind of a dick so I wouldn’t vote for him.

I was on Nickelodeon game show Get the Picture back in the early 90s. I was 12. I won $500 and a bike. I had to pay taxes in both (nearly half their total worth), and the bike was trash. I already had a much better one. I donated it to recoup the loss.

This was season 2. Season 1 had better prizes, and my friend, who was also on (they scouted our school) got a much better haul.

I won a radio contest for free season tickets and a press pass for the Raiders. It was cool as hell. The only whack part was having to pay taxes on the value of the tickets as income, but I got to do a lot of cool stuff.

I got to meet Ice cube, most of Green Day, and a number of then current/ former players. I’ve always wondered if I was somehow related to Tebow mania being a thing. I was sitting in the press box next to someone who said he worked with the Broncos. We started discussing Tebow, and how bad he was. I told him something along the lines of “Tebow can’t throw to save his life. Idk why they don’t try to run the option with him. It worked in college, and it can’t get any worse than what we’re seeing.” The 1st half , the raiders were up big. The 2nd half Denver runs almost exclusively option plays, and came back to win. They continued to do so the rest of the season and turned their season around/ got into the playoffs. It could have been a complete coincidence, but I always wondered if that guy had any say, or talked to someone who did about it.

I got to network my way into an internship with the team the next year. I tried to make a career of it. That didn’t work out, but it was a helluva life experience. Wouldn’t have traded it for the world.

I had a friend who won an episode of jeopardy, no issues getting paid out. (he lost on the next episode)

When I was a kid, my dad won a trip for 2 to Hawaii by being the 7th caller on a radio station. No issues with that either and they let us buy on a 3rd person so I could go with my parents.