Grigori Rasputin
Multiple assassinations in 1916
Rasputin was a creepy mystic who had the Empress of Russia wrapped around his finger for some reason, and the upper class of Russia was worried that he’d get too much power. So they plotted to assassinate him.
First, they poisoned him with food laced with cyanide. He asked for wine to wash it down. They gave him poisoned wine. He drank 3 glasses. Nothing happened.
So they just decided to shoot him instead. He took several shots to the body, and kept on fighting back. So they shot him in the head, and he stayed down.
To make sure he was gone though, they wrapped him up and threw him in the icy river. Even then, the conspirators weren’t 100% sure he was dead.