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The top five hardest NBA players to guard are: 5) Kevin Durant, 4) Hakeem Olajuwon, 3) Kareem Abdul-Jabbar, 2) Shaquille O'Neal, and 1) Michael Jordan. we got the top five hardest NBA players of all time to guard at number five we have Kevin Durant at number four we have Hakeem Olajuwon at number three we have Kareem Abdul-Jabbar at number two we got Shaquille O'Neal and at number one we got Michael Jordan