Sentence:  He was also at the same time gaining practical experience as a safe breaker and <WSD>highwayman</WSD> , and learning how to shoot to kill from a Neanderthal convicted murderer named Gene Geary , later committed to Chester Asylum as a homicidal maniac , but whose eyes misted with tears when the young Dion sang a ballad about an Irish mother in his clear and syrupy tenor . 
Meaning of the word marked with <WSD> tags:  a holdup man who stops a vehicle and steals from it