ANGELO BRUNO was boss of the Philadelphia crime family from 1959 to 1980. Bruno was nicknamed “The Gentle Don” for his approach to peacefully resolving conflicts rather than resorting to violence. This mug shot is from his 1963 arrest for loansharking at age 53, charges that didn’t stick.

In 1980, decades of relative peace in the Philadelphia mob was ended when the aging Bruno was assassinated in a hit ordered by his right-hand man and closest confidante. The resulting power vacuum ignited an infamously bloody four-year Philly mob war.