Rasputin

Grigori Rasputin was the famed 'holy man' who gave counsel to the last Czar of Russia. He was also incredibly hard to kill. In an elaborate assassination plot Prince Felix Yusupov and Dmitri Pavlovich laced wine with cyanide. Once Rasputin was drunk with the poisioned wine they shot him at close range, hitting his chest and liver. Rasputin; however, awoke and tried to escape. His escape attempt was discovered and he was shot again and beaten, including getting kicked in the eye. Rasputin, some how still alive was then thrown into the freezing cold, Malaya Nevka river. His body was discovered a few days later. The Soviets came to power soon after his death.