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Don't know how far back we'd have to rewind the clock in order to be evaluating a relatively healthy Monson, but I saw him in matches against guys like Almeida, Ribeiro, Brandon Vera, Dave Avellan and others during the early 2000s. The majority were GQ matches at Marist High School, but I think I also might have seen him in a match at a Maxercise tournament & in a few matches at a Naga Battle at the Beach ('03 or '04. Whenever they first had an Expert division & it carried a cash prize).
Overall, it was clear he was very hard to turn or sweep, but I don't recall a lot of impressive takedowns. His matches tended to be dull.
Now, in his defense, his reputation sort of preceded him & guys often pulled guard. But, I do recall instances where a few would choose to fight the standup battle with him (Almeida & Avellan come to mind) and would do better than I would of expected [given Monson's wrestling credentials].
What weight did Monson wrestle in college? If he was at 190 or heavy, that might be part of your answer. Obviously, you are going to see less mobile attacks in general at a heavier weight than say, 125 or 157. The upper weights often come down to one takedown, or riding.
The other thing that is worth pointing out, by the time a college wrestler's career is over and moves to BJJ, for instance, they are probably 22 or 23, but they have the injuries of your average 40-50 year old. No joke. Wrestling 100 something matches for 10-15 years, cutting weight year round really takes a toll. Getting into BJJ at 24-25 you have already missed a lot of your athletic prime.
Even good wrestlers in BJJ are often not drilling takedowns that often. You might do maintenance, but you are not going to spend that long on something you are already far ahead on. So things get rusty.
Wrestlers often might be tactical in close matches too, knowing if they can keep it close and decide the match by a takedown, that will almost always favor them. The high flying match is one they stand a good chance of getting caught in.