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For Mstislav Mstislavich the Bold, see Mstislav the Bold

Mstislav of Chernigov, or Mstislav the Bold (Russian: Мстислав Владимирович Храбрый), was the earliest attested ruler of Chernigov (Chernihiv). He was Vladimir the Great's son, probably by Rogneda of Polotsk, although his exact position in the family has been disputed. It is not clear, for instance, whether Yaroslav the Wise was his younger or elder brother.

Mstislav is believed to have engaged imperial masters from Constantinople to build Chernigov's Saviour Cathedral for him.

He was about 10 years old, when his father baptised himself and his family. On this event, Mstislav received the Christian name of Constantine, alluding to the first Byzantine emperor, and was dispatched to rule Tmutarakan on the Black Sea. His relations with the Empire were cordial for the most part. In 1016, he subdued the last Crimean strongholds of the Khazar, led by Georgius Tzul. This campaign, conducted in conjunction with Byzantine forces, helped the Greeks to reassert their control of the Crimea. Mstislav demonstrated his military prowess again in 1022, when he subjugated the Circassians and vanquished their leader Rededya in a single combat.

Two years later, while Yaroslav was away from Kiev, Mstislav led the Khazars and his other subjects against the capital of Kievan Rus'. When the Kievans refused to lend their support to his cause, he routed their army near Listven. Thereupon Kievan Rus' was partitioned between Mstislav and his brother, with Yaroslav remaining to rule the western territories, and Mstislav choosing Chernigov as his capital. In 1031 both brothers were involved in the Galician campaign. Later the same year, Mstislav's fleet, joined by the Alans, routed the Shervanshah's army near Baku and sailed up the Kura River, thence proceeding to Armenia.

Upon Mstislav's sudden death in a hunting accident (1036), his vast realm passed to Yaroslav. In the words of the Primary Chronicle, "his body was deposited in the Holy Saviour's church, which he had laid to, as its walls were already high enough for a mounted horseman to reach the top with his outstretched hand". This cathedral remains the only extant monument of Mstislav's reign.

The name of Mstislav's spouse is known to have been Maria, and they had a son, named Eustaphius, who predeceased his father. Some scholars have identified this prince with "a Russian king's son", who married Canute the Great's sister Aestrid (according to Adam of Bremen's scholia). Upon returning back home from Russia, Aestrid was briefly married to Robert the Devil.

In the later 17th century, when the Velvet Book was being compiled by the Russian aristocracy, the Lopukhins, Ushakovs, and several other noble families, seeking for illustrious pedigrees, asserted their descent from Mstislav's postulated son Roman, who was allegedly married to Rededya's daughter. This fable has been repeated in numerous genealogical compilations of later date.