I ended up choosing the design on the right to develop which is kind of a mix between Tom Berenger and James Coburn:
He's a hustler and a gambler so I wanted to study some reference to push his character:
To make him a bit more appealing and diverse, making him a family man was a good a challenge. That way he can justify actions by saying it's done for the greater good. These drawings below illustrate two different personalities. At home, he's king(the root meaning of Henry means 'home ruler') but out in the real world, he's a scam man.
More to come later.