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He was the second son of SvyatoslavII Yaroslavich. He married Feofania Muzalon. They had five sons, Vsyevolod, prince of Chernigiv and also prince of Kyiv; Igor, who also became prince of Kyiv briefly; Gleb, prince of Kursk; Svyatoslav, Ivan. Some family members are shown on this chart. and more generations are on this chart. He was assigned first to Vladimir-in-Volynia (1076), then he fled to Tmutorokan on the Taman penninsula (1083-94). He ruled Chernigiv in 1078 and from 1094 to 1096. He was then assigned to Novgorod Severski (1097-1115) when the family council divided up the lands at the conference of Liubech. He was more aggressive than his brother, David, in asserting the position that the grandsons of Yaroslav should receive the domains held by their fathers from him as hereditary patrimonies, rather than constantly shift their home towns. In this effort he fought the Monomashchi for years, enlisting the aid of the Polovtsi. The House ofOl'govichi is shown on this chart.


1076 - Holding Vladimir-in-Volynia, he is sent by the usurper, Svyatoslav II, to assist King Boleslaw of Poland against his uncle, Izyaslav I.
1076 - His father, Svyatoslav, dies, he goes to Chernigiv, his father's land, but the returning prince, Izyaslav, gives Chernigiv to his own brother, Vsyevolod Yaroslavich. Oleg flees to his brother, Roman, in Tmutorokan.
1078 - Oleg and his cousin, Boris Vyacheslavich, (an izgoi son of Vyacheslav Yaroslavich, prince of Smolensk) obtain Polovtsi troops and attack Chernigiv, driving Vsyevolod out.- He holds Chernigiv temporarily- Izyaslav and Vsyevolod retake the city - then Oleg and Boris attack them. In the battle both Boris and Izyaslav are killed and Oleg flees again to Tmutorokan. His older brother, Gleb, dies this year also..
1079 - His older brother, Roman, obtains Polovtsi and attacks Vsyevolod, who is now prince in Kyiv. Vsyevolod bribes the Polovtsi to kill Roman.
1083-94 - Oleg is ruling Tmutorokan except for 1083-85 during which years he is held by Byzantines on Rhodes, having been kidnapped by the Khazars at Vsyevolod's instigation.
1085 - returning to Tmutorokan Oleg has to drive out David Igor'yevich and Volodar Rostislavich.
1094- Oleg again mounts a campaign with main assistance of Polovtsi to take Chernigiv, which is now held by a cousin,Vladimir Monomakh. Since another cousin,Svyatopolk II Izyaslavich, is prince at Kyiv. After a week of fighting Vladimir flees to his own homebase at Periaslavl.
1095 - Prince Svyatopolk and Vladimir Monomakh prepare to campaign against Polovtsi, but Oleg refuses to participate. Vladimir's son, Izyaslav, takes Oleg's dependency at Murom.
1096 - The family leaders (princes) insist that Oleg join in discussion of the family situation. He continued to refuse to have anything to do with the others, so in a united front they drive him out of Chernigiv to Starodub. After being besieged for weeks, Oleg reluctantly agrees to accompany his brother, David of Smolensk, to the conference. However, enroute he changes course and marches to Murom to attack Izyaslav Vladimirovich. Izyaslav defends the town but is killed, whereupon Oleg takes Murom, Suzdal, and Rostov as well. At this Vladimir's other son, Mstislav, who holds Novgorod, sends word to Oleg to back off and get out of Suzdal and Rostov. Mstislav also offers Oleg peace and to interceed with his father, Vladimir Monomakh. Oleg pretends to agree. Mstislav even states that he won't hold Oleg's killing of Mstislav's brother, Izyaslav, against him if he will agree to peace. Oleg refuses and sends his brother, Yaroslav Svyatoslavich out toward Novgorod with tax collectors. Mstislav has no choice but to march on Suzdal. At his approach Yaroslav Svyatoslavich rapidly retreats and warns Oleg. Oleg quickly withdraws fristto Rostov and then to Suzdal when he sees that Mstislav is not stopping at the Volga. Mstislav advances to Vladimir on the Klyasma. Out of spite Oleg burns Suzdal before retreating to Murom. Mstislav again sends word offering peace. Oleg again pretends to accept in order to lull Mstislav and Mstislav believes him. Then while Mstislav disbands his war band and waits around Suzdal, Oleg sneaks up to the Klyaz'ma and prepares to attack. Oleg expects Mstislav to retreat but this time Mstislav is no longer to be fooled with. Mstislav gathers his troops and Oleg stands fast. At this point Mstislav receives word that his brother, Vyacheslav is arriving with Polovtsi allies sent by their father, Vladimir. Now Vyacheslav and Mstislav attack Oleg and his brother Yaroslav. Mstislav has Vladimir's war banner and this frightens Oleg. Oleg is forced to flee to Murom and then to Riazan. Mstislav follows, freeing the cities and releasing the prisoners. Now Mstislav is back with troops and forces Oleg to agree to attend the meeting. Mstislav returns to Novgorod.
1097- Oleg attends the famous family conference at Liubech, north of Kyiv. In the general compromise Oleg looses Chernigiv to his own brother, David, but is given a part of the Chernigiv lands with Novgorod-Severski as capital. Their brother, Yaroslav, gets Murom and Riazan back. As part of the compensation some other towns are reallocated to them. From this time the three Svyatoslavichi are content to stay put and not contest the throne in Kyiv.
1100 - Oleg and David attend another family meeting at which arrangements are confirmed.
1101 - Oleg participates in family conference to discuss the Polovtsi problem and still, in 1103, refuses to campaign against them.
1104 - Oleg is now ready to cooperate. He assists Prince Svyatopolk against Gleb Vseslavich at Minsk.
1107 - Oleg on the one hand agrees to campaign against the Polovtsi, but on the other arranges marriage for his son, Svyatoslav, with a Polovtsi princess.
1115 - Oleg dies and is burried in the cathedral at Chernigiv.


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