After mulling it over I was reminded of some City of London/ Wall Street "rogue traders" who as the markets kept going against them simply kept "doubling up". Some of these were lucky, but some destroyed centuries old financial institutions; most notably Bearings.
Thus I give you Nick Leeson, a 1980's US Grant. He was profile by the superb Adam Curtis in this documentary (1/6):
He was played in the film dramatisation by Ewen "Obi-wan Kinobi" McGregor: