I have been doing this a long time, and was asked the question a few days ago. Some of the answers made me smile as i recalled them.
A few of the more memorable ones:
A bottle of 1962 Romanee Conti on a wall in restaurant in the heat in Florence that had been there for 30+ years, which I bought for a $100, and yes it had turned.
Finding an incredible list at a country club near Williamsburg, and being allowed to buy wines off that list. They filled two cars as it was worth hiring a second car to bring all the wines back to NY.
Being asked by a close friend, a lawyer, to assess and buy the wines of the widow of his senior partner. She turned out to be one of the most foul people I have ever met, and after threatening to walk out (actually it wasn’t a threat, I really wanted to go, and stayed as a favor to my friend) I bought three bottles, each turning out as vile as she was.
Buying the contents of a cellar in Connecticut. Just as we were getting ready to leave, a large Mercedes comes screeching to a halt and the wife and her attorney get out of the car stopping the sale. Lots of shouting and screaming. And it was several years before I was able to find another bottle of Trotanoy 1961.
Buying Champagne from a mom and Pop store owned by Koreans. They had the most fantastic collection of Krugs, Salon old DP etc, and although they barely spoke English, we just loved the experience. We ended sitting in the store for a couple of hours drinking with them, and the drunker we got, the better we communicated.
The semi annual pillages to Boston, DC etc. When I was young and naive, we shared a large van and headed to different places, where we bought wine. We saved for months for these trips, and got some incredible buys, and occasionally, we would open a bottle in the parking lot, sample the wine, and if it was good, go back and buy the rest.