Ivan Isayevich Bolotnikov (Russian: Ива́н Иса́евич Боло́тников) (1565-1608) was the leader of a popular uprising in Russia in 1606–1607 known as the Bolotnikov Rebellion (Восстание Ивана Болотникова). The uprising was part of the Time of Troubles in Russia.
Little information is available about Ivan Bolotnikov’s life before the uprising. It is known that he was a kholop and belonged to the household of Prince Andrei Telyatevsky. It appears that Bolotnikov fled from his master’s estate, then was captured by the Crimean Tatars, and sold to the Turks as a galley slave. He somehow managed to escape from his owners, reached Venice, and then was captured in Poland en route to Russia by the associates of Mikhail Molchanov (one of the assassins of Feodor Godunov, who had successfully fled from Moscow and was again contemplating the second coming of False Dmitry).
Molchanov sent Ivan Bolotnikov to the town of Putyvl to meet a voyevoda named Grigory Shakhovskoy. The latter received him as the new tsar’s envoy and put him in charge of a Cossack unit. Ivan Bolotnikov used this opportunity to muster a small army of runaway kholops, peasants, outlaws, and vagabonds, disgruntled at the powers that be. He promised them to exterminate the ruling class and establish a new social system. By the order of Grigory Shakhovskoy, Bolotnikov and his army advanced to Kromy (today’s Oryol Oblast) in August 1606, defeating the Muscovite army under the command of Prince Yury Trubetskoy. From there, he moved towards Serpukhov and ravaged the city.