re: What's the biggest bet...you didn't win?

At a job I had back in college, there was a local bookie that would drop off cards for each weekends football game. I never was serious about them but usually put up a buck on a twelve team parley. I think the twelve teamer paid 500 to 1 and 11 out of 12 paid 100 to 1. One weekend I decided to put 5 bucks on a 12 teamer. Lost one fricking pick. Still made 500 on a 5 dollar bet though.

Bookie said he never felt so good paying someone money.

Worst part was since it was basically free money I decided to put it into a stock. The stock was my brothers company which was selling at I think 97 cents per share. I threw the whole 500 into it and watched it drop to 23 cents. I dropped out and threw what I had left into some dumb arse penny stock. Failed. So I never saw a penny really. Years later I looked back at the original company and it had grown to some ungodly number. So I really missed out. I need to see what it's at now.

here it is

Not like it was something I could retire off of, but that would have been a hell of a return on a 5 dollar investment.