The kill in episode 19 is the most impressive. He actually used ocean water to ricochet bullets to his targets. The manga is technically the canon but the skills are similar.
If Golgo's win condition is kill the target then yeah he takes it. Both him and Ryo are similar in stats but I'd give the edge to Ryo who's usually forced to come up with creative ways to not die on the spot (as opposed to Duke who usually has to come up with creative ways to kill, usually from afar) and has experience fighting guys just like him and Golgo. (Umibouzu for instance). If the two engage in combat I'd give it to Ryo.
If all he has to do is kill Ryo's client though it becomes a lot harder for Ryo to take the bag. As was said Duke is usually able to come up with out of the box ways to kill someone. If he decides to approach from range he'll likely kill whoever the client is before Ryo knows what happened.
This is all assuming a city setting where there's open space to travel and not confined to like a night club somewhere.
Yeah I assume the client dies as a matter of course.
Range would matter a lot too. Don't know how Ryo would deal with a sniper of Golgo's caliber. But in close combat he held his own against that snake man and those mutants too.
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