Vladimir the Bold

Vladimir Andreyevich the Bold (Russian: Владимир Андреевич Храбрый; July 15, 1353 – 1410) was the most famous prince of Serpukhov.

A grandson of Ivan Kalita, Vladimir inherited Serpukhov, Borovsk, and a third part of Moscow from his brother at the age of 5.

Pursuant to the treaty, Vladimir helped Dmitry to fight Tver (1375), Ryazan (1385), the Livonian Knights (1379), and the Republic of Novgorod (1392).

Although they made peace the same year, Vladimir was forced to leave Serpukhov for Torzhok following Dmitry's death and enthronement of his son Vasily I.

His granddaughter Maria of Borovsk married Vasily II and gave birth to Ivan the Great, who expelled the last princes of Serpukhov to Lithuania.