My first was Romeo and Julieta Exhibition #4 that someone had gifted me. That was sometime in 2000 IIRC. I had just bought like 5k worth of Fuente products, mostly short stories and similar because I liked them so much.. After that RyJ I sold almost all of the fuentes and rarely ever smoked them again. Although to this day I still enjoy a short story.
After that I started spending some serious money on Cubans. Found forums to discuss cigars and traded a lot to discover all the flavors that could be had in a cigar.. Found out about of box of PSD4's in London that Mitchell had for sale. 94 and they were like 750 bucks.. Of course I had to have them.. Sublime and still one of the top 15 cigars I have ever had. Unfortunately I gifted most of them away. They were so good I had to share them with friends LOL. In about 4 years I accumulated 100's of boxes. A bunch of us even had the Bolivar gold medals reproduced. Just a group buy, cant even remember how many boxes got made or the details surrounding them.