I was thinking of this and thought it might make a good thread.
In the best category:
My grandpa traded a pair of boots for his first car (A Model T.) ISTR he was about 13 or 14 at the time, but he lived out in the country and drove it anyway, unlicensed.
Worst:
I had a friend whose parents bought him his first car - a 1985 RX-7. For some inexplicable reason, he took it off road a few times and tore it up pretty good. Apparently he decided he liked driving off-road better because he traded the car for a go-kart. The go-kart didn’t run, but he thought he could fix it. It turned out he couldn’t, so he traded it for a pit bull, which ran away shortly thereafter. From RX-7 to nothing in 2 simple trades.