2. Johnny Unitas
Johnny Unitas was a legendary NFL quarterback. He was much beloved and is considered to be one of the greatest quarterbacks of all time. Unitas had numerous NFL records under his belt when he retired. Some of these records have been broken by others but there are some that still remain his. Recently his longtime held record for most consecutive games with touchdown passes (47) was broken.
At some point in his life Unitas thought it best to attempt to invest his wealth into numerous different business ventures. He attempted to start restaurant and bowling alley chains, amongst a few others. Unfortunately for the legend none of his business attempts made him any sort of money and instead he lost money. His determination to start a business led him into even more failed endeavors and in 1991 Unitas Management Corp was forced to file for bankruptcy. Sadly, two years later he died of a heart attack.