Yaroslav II Vsevolodovich (Kiev, 1139–1198) was a Rus’ prince (a member of the Rurik dynasty). He was prince of Ropesk (c. 1146–1166), of Starodub (1166–1176), and of Chernigov (1176–1198). When he became a monk before his death, he took the name Vasily.
He was the second son of prince Vsevolod II Olgovich of Chernigov (who later became Grand Prince of Kiev) by his wife Maria Mstislavna (a daughter of grand prince Mstislav I Vladimirovich of Kiev). His father died on August 1, 1146; and he probably became the prince of Ropesk (a town, located southwest of Starodub, which lay on the river Irpa, a tributary of the Snov River).
When the wife of grand prince Izyaslav III Davidovich of Kiev (whose husband had been expelled from Kiev by prince Yaroslav Volodimerovich of Halych on December 22, 1158) came to Ropesk, Yaroslav showed every courtesy, although Izyaslav III Davidovich had declared war on the Olgovichi (the ruling dynasty of Chernigov).
In 1162, the younger brother of grand prince Rostislav I Mstislavich of Kiev, Vladimir Mstislavich seized Sluchesk which was the domain of the Olgovichi. By capturing the town, he transgressed against prince Svyatoslav II Olgovich of Chernigov (Yaroslav’s paternal uncle) whose right Rostislav Mstilavich had pledged to defend. The grand prince of Kiev therefore sent a number of junior princes, including Yaroslav, to expel his brother; on seeing their large force Vladimir Mstislavich sued for peace and went to his brother in Kiev.
On February 15, 1164, Svyatoslav II Olgovich died, and Yaroslav’s brother, Svyatoslav III Vsevolodovich assumed control of Chernigov. The latter relinquished Novgorod-Seversk (today Novhorod-Siverskyi in Ukraine) to their cousin Oleg Svyatoslavich; in doing so, Svyatoslav Vsevolodovich bypassed Yaroslav who, as Oleg Svyatoslavich’s genealogical senior, had prior claim to the town.