Anthropomorphic animals who are professional thieves, and are the leaders of a team of three (the Cooper Gang and Team Dark). Both of them have had run-ins with the authorities and have actually worked for them as well, with Sly teaming up with Carmelita on multiple occassions and Rouge being a G.U.N. agent. Both of them have recovered numerous treasures from around the world and have often flirted with their adversaries.
I feel that with sly coopers time manipulation and wider arsenal that he can beat Rouge