I always thought Ray Patriarca's son Ray Jr was kinda ugly as he got older. There's one picture of him shown on an espn documentary about the Providence Mafia (you can still find it on youtube). He was balding pretty badly and wearing some pretty big glasses, and huge lips too!

In Mark Silverman's book it did show a picture of Jr. as a young man in one of his mugshots. He wasn't half bad looking when he was young (I guess being the boss took its toll on him!). Ray Sr always aged pretty well in my opinion though.