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I don't think you are giving enough credit to Alves, Fitch and Koscheck of 2008, they would beat some guys in the top 10 in the 2020 rankings IMO. Karo, Sanchez, Hughes and Serra might be able to pull off an upset over someone in the 2020 top 10 rankings but I wouldn't favor them like I would Alves, Fitch and Koscheck against some of the top 10 guys of today though.
Honestly, prime kosheck matches up well with Usman and prime Fitch matches up well with Colby.
I don't think the evolution in this division is nearly as great as TS implies.