Vince and Linda McMahon (Bankrupt in 1976): The brains behind World Wrestling Entertainment (NYSE:WWE) clearly didn’t have a head for finance in the beginning. The couple was in the hole $1 million in debt as the wrestling empire started to blossom. That included footing the bill for such crazy schemes as a failed Evel Knieval attempt to jump Snake River Canyon and a fight between Muhammad Ali and Japanese wrestler/martial arts star Antonio Inoki. Oh yeah, and they didn’t like the IRS too much — racking up $142,763 in unpaid income taxes over five straight years.
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