During the Mongol invasion of Russia, the youngest of Vsevolod III's sons, Ivan, made Starodub his seat (1238). His descendants ruled the tiniest of Russian principalities for more than a century, desperately trying to fend off attacks by two powerful neighbours—Muscovy and Nizhny Novgorod. Their ephemeral power came to an end in the 1370s, when the town was eventually annexed by Dmitry Donskoy. Thereupon numerous scions of Starodub dynasty moved to Moscow, where they formed the families of Princes Gagarin, Khilkoff, Romodanovsky, Pozharsky, and many others.
During the Time of Troubles, the town was completely burnt to the ground by the Polish warlord Alexander Jozef Lisowski, who ravaged the area in March of 1609. Some historians believe that Prince Dmitry Pozharsky, who helped Russia to survive those turbulent times, lies buried in Starodub, the demesne of his forefathers.