I can only remember four trades I did as a kid, and none of them were very good… 
- My Base Set Chansey for a Base Set Pidgey, Pidgeotto, and Vulpix (as a kid I mainly wanted more cards, and didn’t really care about Holos
More about this first trade here) - My Jungle Set Holofoil Snorlax for a WB promo Mewtwo (this wasn’t too bad of a trade at the time, although it certainly would be today)
- My Reverse Foil Legendary Collection Moltres for an Ancient Mew (yeah, bad move…)
- My Ancient Mew for a Japanese Neo Genesis Steelix
The Chansey, Snorlax, and Moltres were all pulled myself. And the last two trades actually come down to my Reverse Foil LC Moltres for a Japanese Neo Genesis Steelix (with about a year in between trades).
Greetz,
Quuador