The most likely expensive dud you're going to see is aged Burgundy reds. Many don't make it.
Very old red wine (e.g. 30+ years), if it's not fortified or a dessert wine, is also not particularly pleasant. I've had some very famous Bordeaux from some celebrated 70s vintage, a sip from Hedonism Wines in London, and it was very much not worth it; more than anything else, it reminded me of clothes in an old person's closet.
On the other hand, the same day I had a sip of something sweet from the 19th century - like 1898 or something - from Crimea, and it wasn't bad. It wasn't great, but it wasn't bad or undrinkable either. Might have been related to these batches - https://quillandpad.com/2020/07/21/the-massandra-collection-...
Very old red wine (e.g. 30+ years), if it's not fortified or a dessert wine, is also not particularly pleasant. I've had some very famous Bordeaux from some celebrated 70s vintage, a sip from Hedonism Wines in London, and it was very much not worth it; more than anything else, it reminded me of clothes in an old person's closet.
On the other hand, the same day I had a sip of something sweet from the 19th century - like 1898 or something - from Crimea, and it wasn't bad. It wasn't great, but it wasn't bad or undrinkable either. Might have been related to these batches - https://quillandpad.com/2020/07/21/the-massandra-collection-...