10. Javier Escano
Javier Escano (Jose Zuniga) was a fundamental part of PD's ninth season. He was a friendly philanthropist to the public, and ruthless crime boss behind closed doors.
Escano's manipulation of Anna Avalos (Carmela Zumbado) is the real crime, however, when considering everything she had to go through to infiltrate his crew.
Escano's fate was ultimately secondary to the broken friendship between Avalos and Hank Voight (Jason Beghe), but the fact that he was the person who caused it to happen in the first place meant he more than deserved the fate he got courtesy of Avalos' knife.