Philly has a ton of these--guys who were boss or underboss or consig and whose sons entered the life:

Scarfo and son, mentioned above
Joseph "Chickie" Ciancaglini and his sons John, Michael and Joe
Phil Testa and Salvie Testa
Chuckie Merlino and Skinny Joey


Then some guys who were powerful if not top-tier:

Salvatore "Wayne" Grande and Domenic Grande, even though his dad flipped
Frank "Chickie" Narducci and his sons Phil and Frank
Anthony "The Blonde Babe" Pungitore and his sons Joe and Anthony

Then I feel like the Scafidi family also has several generations, at least one of whom flipped.