Lol george you meanie :P

Yea its hard to explain the way he thinks but he says I did the wrong thing in betting $100 on that underdog.
"Most of the time they lose, and wham you lose $100 and youll never get to bet on that exact game again to make the money back"

Yikes. Anyway I found this online:

Assume I engage in a gambling strategy that has 999 chances in 1,000 of making $1 (event A) and 1 chance in 1,000 of losing $10,000 (event B).

My expecation on this bet is a loss close to -9. The frequency or probability of the loss is totally irrelevant; it needs to be judged in connection with the magnitude of the outcome. Odds are that we would make money by betting for event A, but it is not a good idea to do so.

This mathematician guy Nikolas Taleb suggests that most people (including those with advanced degrees or MBAs) would be enticed to act on the winning odds (Event A) due to the inordinate focus on the frequency despite the understanding that an occurrence of a low probability event may affect a greater deal relative to the outcome than the combined wins.

So at least it seems like theres other people out there who cant grasp it.