re: What's the worst investment you've ever made.....

I worked at United Companies during the late 90's and although the stock was falling I liked the fact that senior management gave regular updates to the rank and file that seemed pretty honest about the likely troubles ahead.

It turned out they had indeed been honest - to this day I have never seen an executive team that leveled with the rank and file as much. The problem was that they were very right that times were tough and so I lost over 95% on my investment when I bought at $5/share.