The funny thing is, I'd say after 25+ years of training across seven or eight martial arts, I'd conclude that winning in the clinch is the ultimate PROOF you're the better martial artists.
'inside' is the safest place to be, AND you have more weapons at your disposal. When you're physically attached to the other fighter, it's much more about who's smarter, and better trained, and much less about who's a better athlete.
In this case though, JDS was up against a guy who just wants to attach himself to you, put the pace on you and beat you up. It's not subtle.
Solution: JDS has to get more mobile. If he gets ten clean shot's at Cain's head, Cain will go down. But to get ten clean shots, he has to keep Cain off of him. Standing in front of him or retreating straight backwards will fail.