This is a story that I've always hated because I think it is very very unlikely to be true. If he actually did play blackjack, I'm curious to know how many hands he played, how much he was betting per hand, what casino he was playing at, etc. If he bet it all on one hand, what if he was dealt A-A and didn't have the money to split?

I think somebody who is reckless enough to gamble the remaining funds of the company, is not disciplined enough to walk away from the blackjack table after having won just enough for the fuel payment.

If he actually did play blackjack, it would be more likely that he started out winning, won enough to pay for the fuel, but then continued gambling and gave it all back.