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Skirgaila, also known as Ivan/ Iwan ( or 1354 – 11 January 1397; baptized 1383/1384 as Casimir), was a regent of the Grand Duchy of Lithuania for his brother Jogaila from 1386 to 1392. He was the son of Algirdas, Grand Duke of Lithuania, and his second wife Uliana of Tver.
When Jogaila was preparing for the Union of Kreva, Skirgaila was actively involved in the negotiations and even headed a diplomatic mission to Poland. The negotiations succeeded and Jogaila married Jadwiga of Poland and was crowned as King of Poland in 1386. He appointed Skirgaila on 13 March 1386 as governor in Lithuania, not only on his behalf but also on behalf of queen Jadwiga and Polish Crown.Frost 2015, p. 77.
As ruler of Lithuania, Skirgaila had to deal with his oldest brother Andrei, who still was refusing to accept Jogaila as a Grand Duke. First he defeated Andrei's ally Sviatoslav II of Smolensk in a battle of the Vikhra River near Mstislavl on 29 April 1386, during which Sviatoslav lost his life. Sviatoslav son Yury of Smolensk was forced to accept Lithuanian suzerainty in exchange of princely throne. Later Skirgaila attacked Polatsk; his first expedition in October was unsuccessful, but the next on March 1387 resulted in Andrei's capture and death of his son Simeon, who was killed in a battle.Frost 2015, p. 78. Next month Skirgaila was invested in Polatsk and once again pledged his loyalty to Jogaila, Jadwiga and Polish Crown, promising return of his land in case of his heirless death. Skirgaila was now directly ruling over large portion of Lithuania, including the duchy of Vilnius, ruled on behalf of Jogaila. On February 20, 1387, Jogaila elevated his brother above other Lithuanian princes and extended his authority over Ruthenian lands.
In 1389, he started a new civil war, but after an unsuccessful attack on Vilnius he had to seek help from the Teutonic Knights. In 1392 Jogaila and Vytautas signed the Ostrów Agreement, and Vytautas became his regent of the Grand Duchy of Lithuania. The Duchy of Trakai was returned to Vytautas as his patrimony.
As a compensation Skirgaila received a portion of Volhynia and Kiev since 1395. The circumstances surrounding his death are not entirely clear. He was interred in the Kiev Pechersk Lavra.
Skirgaila had one known child, a daughter by an unknown mother, who was mentioned in sources in 1393.Table 1 in: Borkowska, Urszula (2012). Dynastia Jagiellonów w Polsce (in Polish). PWN. ISBN 9788301205331.
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