Skirgaila 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.

Jogaila, later Władysław II Jagiełło, was Grand Duke of Lithuania, later giving the position to his cousin Vytautas in exchange for the title of Supreme Duke of Lithuania (1401–1434) and then King of Poland (1386–1434), first alongside his wife Jadwiga until 1399, and then sole ruler of Poland. Born a pagan, he converted to Catholicism in 1386 and was baptized as Ladislaus in Kraków, married the young Queen Jadwiga, and was crowned King of Poland as Władysław II Jagiełło. In 1387, he converted Lithuania to Catholicism. His own reign in Poland started in 1399, upon the death of Queen Jadwiga, lasted a further thirty-five years, and laid the foundation for the centuries-long Polish–Lithuanian union. He was a member of the Jagiellonian dynasty in Poland that bears his name and was previously also known as the Gediminid dynasty in the Grand Duchy of Lithuania. The dynasty ruled both states until 1572, and became one of the most influential dynasties in late medieval and early modern Europe.