Descendants of Grand Prince Iaroslav I of Kiev (died 1054) ruled the principality until 1125. Following the death of Vladimir Monomakh, Grand Prince of Kievan Rus', Vladimir's son Mstislav I Vladimirovich became the Rus' over-king and Mstislav's own son Rostislav Mstislavich became Prince of Smolensk (ruled 1125–1160). The principality gained its own Orthodox bishopric under the Bishop of Smolensk in 1136. The principality contained a number of other important cities that usually possessed subordinate status, notable among them Bryansk, Vyazma and Mozhaysk.
In 1386, Prince Sviatoslav IV of Smolensk[ru] was killed in the Battle of the Vikhra River against the Lithuanians when he supported Andrei of Polotsk and his rebellion against his younger half-brother Jogaila. However, Skirgaila, the leader of the Lithuanian forces in battle, wedded to Sviatoslav's niece, and granting permission to Yury of Smolensk was in command, to succeed his father.[1] In 1395, Grand Duke Vytautas of Lithuania took Smolensk and installed his governor there. Four years later, Vytautas was routed by the Tatars in the Battle of the Vorskla River. In 1401, Yury and Oleg Korotopol of Ryazan made use of his plight to retake Smolensk and Bryansk. Vytautas attempted to retake Smolensk in 1401 and 1403. In 1404, boyars of Smolensk opened the city gates to Vytautas and surrendered the city in 1404.
The famous trade route from the Varangians to the Greeks passed through the principality and was an important source of income for its rulers. The trade with Riga and Visby developed in the second half of 12th and 13th centuries. Wax was the main export followed by honey and furs; the main imports from Europe were textiles and later, salt, delicacies and wine.[2]