On this day, Oct. 18, in 1999, John “Junior” Gotti, who led the Gambino crime family while his father was locked away, entered prison himself after pleading guilty to racketeering. Junior’s father, John J. Gotti, known as the “Dapper Don,” was the most powerful crime boss of his era. Gotti made Junior the head of the family and used a committee of captains to help. As one of the few people allowed to visit his father, Junior Gotti could pass on his father’s orders.

In 1997, FBI agents searched Junior’s property and found a typed list of the names of “made” members of the Gambino family. The New York media nicknamed Junior the “Dumbfella.”