#6: Mark Ingram, Sr.
The apple didn’t fall far from the tree in this NFL family tale. The father of a current and active running back carved his own mark in football history as a wide receiver for the New York Giants, playing a pivotal role in their triumphant Super Bowl win in 1991. Yet, his life took a tumultuous turn after hanging up his cleats in 1996. Once a celebrated athlete, Senior found himself ensnared in a web of financial troubles. He ventured into the murky waters of money laundering and attempted to outsmart the IRS.

However, his schemes unraveled, leading to a seven-year prison sentence and hefty fines. The saga didn’t end there, as he further complicated matters by evading authorities when required to surrender, adding several months to his incarceration. In 2018, a return to prison loomed as courts ruled that he had breached his supervised release terms by possessing a firearm, failing to meet a $500 monthly restitution, and neglecting to notify his probation officer of an address change.