Floyd Mayweather, Sr.
COMPLEX SAYS: The former pro boxer who's now known for helping train his son, Floyd Mayweather, Jr., to an undefeated career record and multiple titles was convicted of trafficking cocaine in the early '90s. Mayweather, Sr. was allegedly part of a drug ring that would smuggle cocaine in laundry detergent boxes. He was sentenced to five years in prison. Seems like a tale straight out of a trap rapper's dream. Oh wait, it is.