$75 for a 1964 Padron Diplomat in Canada. The owner of the shop (won't give his name, since he is starting his own cigar line) had no prices on the boxes, and I went to go fire one up. Well, a few minutes after, he said that'll be $75. I nearly sh!t myself! But he was one of very few shops in Canada with Padron 1964 anniv series and not an authorized dealer. I felt like such an idiot afterward. I even hot-boxed it and smoked the sucker in 45 mins b.c I was so upset. Never had I been soooo sick after that (both physically and mentally)
Besides that, $50 for some Monte C EL2003 back in 2010. But it was fun only having only a hand full of cigars and disposable income! Now I have a collection of 150+ and I'm broke.... lol!
Canada has outrageous prices for cigars... Glad I live in the US now!
But now the most I will pay is $15 for a cigar, unless it's uber rare like the UC Flying Pig at $20.