I was going through my home office and found the loot bag for GenCon 2010. There was a MtG Planechase card in it for Tember City, a Settlers of America 2010 tiny dice bag, a Dungeons & Dragons con exclusive comic book, and some advertisements. Makes me sad I'm missing this year.
If it makes you feel better, that might have been the last year there was any loot bag at all? O.K. maybe not but close.
I have to say though, one of the most seemingly universal moments of Gen-Con nostalgia comes from people cleaning up some largely-ignored part of their home and discovering something from 1-20 Gen-Cons ago, haha. My friends and I celebrate Nerd Christmas every year as an excuse to get together and do some themed gaming, and the present I brought was "a complete set of the Gen-Con Survival Kit one of our members put together for Gen-Con 2002." That came from a particularly deep dive in my parents' basement...haha.