He's definitely fought strikers who were more skilled, but that doesn't really matter. He was had some pretty big physical advantages over them, which he made use of, because why wouldn't he?
Gus and Reyes are big guys close to Jon's size, and Jon couldn't do shit to Reyes for 3 rounds on the feet and Gus almost beat him as well.
Machida has way more skill than both of those guys. He just didn't have the size and reach. P4P, prime Machida would have destroyed Gane, Gus, and Reyes without issue.
Gane doesn't have Machida's skill level either, but not only does he have the size that Gus and Reyes had, he has a fuck ton more of it. On top of it all, he has enough skill on the feet to give Jon trouble anyway. He's a better striker than Reyes.