Probably a round trip YYC-LGA / TPA-YYC on NWA a while back. But, I was upgraded to F for TPA-YYC, so I can't consider that too bad of a deal for the 20,000 miles I spent on it after 5 K delay compensation.

Actually, I think my recent YYC-COS round trip on UA for 20K was a bad deal. But hey, it was only 20 K.

I guess I don't really have a closet full of bad redemption experience.

My BEST redemption was YYC-DFW(stopover)-EZE (stopover) - Iguazu Falls (open jaw) / Punta Arenas Chile - Santiago (stopover) - DFW (stopover) - YYC for 40,000 miles.

My AAgent was a bit clueless Re: stopover rules! Man I wish I could go back to that!