5. Sviatoslav I

With the end of Olga's regency, Sviatoslav ascends the throne as the official Grand Prince of Kyiv. Which side of the tree will he fall off of? Igor's or Olga's? 
A Flatpack History of Sweden
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Klavdiy Lebedev (1852-1916). Svyatoslav's meeting with Emperor John, as described by Leo the Deacon
Klavdy Lebedev, Public domain, via Wikimedia Commons

Miniature 63 from the Constantine Manasses Chronicle, 14 century: Invasion of King Sviatoslav I of Kiev into Bulgaria.
Original: Constantine Manasses, Public domain, via Wikimedia Commons

Slav warrior, russian knyaz Svyatoslav.
Fedor Solntsev, Public domain, via Wikimedia Commons

The Kievan Rus' at the beginning of Sviatoslav's reign (in red), showing his sphere of influence to 972 (in orange)
The Kievan Rus during the reign of Sviatoslav I of Kiev. Red outline shows Rus territory at Sviatoslav's coronation in c. 962;
orange denotes his conquests 962-972. Black arrows - the campaign of Svyatoslav to Khazaria.
White arrows - Svyatoslav’s campaign to Bulgaria.
Byzantine territory in purple; probable sites of Khazar successor states in blue.

Sviatoslav's Council of War by Boris Chorikov
Boris Chorikov, Public domain, via Wikimedia Commons

The Death of Sviatoslav by Boris Chorikov
Boris Chorikov, Public domain, via Wikimedia Commons

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Bibliography

• History of Russia: Volume 2 - Kievant Russia by George Vernadsky
• A Cambridge History of Russia by Maureen Perrie
• The Russian Primary Chronicle