I know Doyle Brunson and Stu Ungar are considered the best to ever play, winning back to back wsop but there wasn't even 100 people in the event back then! I've won several tourney's with more people than that. Doyle makes plays that boggles the mind, all-in on the crappiest of hands. I think Sammy Farha is the best I've seen, really has a feel for players hand strengths.