Despite numerous power struggles in Lithuania, including rebellion by Andrei of Polotsk, conquest of the Principality of Smolensk, and the Lithuanian Civil War (1389–92), Švitrigaila does not appear in politics until 1392.

After the death of his mother Uliana of Tver, Jogaila appointed falconer Fedor Vesna regent of the Principality of Vitebsk.

Vytautas, who just concluded the Ostrów Agreement to become Grand Duke of Lithuania, and Skirgaila gathered an army and captured Drutsk, Orsha, and then Vitebsk.

[citation needed] Probably around 1396 or 1397, Švitrigaila and Fedor, son of Liubartas who was ousted from Volhynia near the conclusion of the Galicia–Volhynia Wars, escaped from Kraków to Duchy of Cieszyn, fief of the Kingdom of Bohemia, and from there to the court of Sigismund of Luxemburg.

Chronicler Jan Długosz hinted that the Pact was in part motivated by the desire to contain growing influence and ambition of Švitrigaila.

The Knights received territorial concessions in Samogitia while Švitrigaila received Podolia (though the territory was de facto governed by Piotr Szafraniec), Zhydachiv, and an annual sum of 1,400 marks from the Wieliczka Salt Mine from Jogaila and the Principalities of Briansk, Chernigov, and Trubetsk from Vytautas.

For a few years, Švitrigaila was loyal to Vytautas and helped to subdue Smolensk and negotiate with the Teutonic Knights regarding the Dobrzyń Land.

Švitrigaila's new territories were by the border with the Grand Duchy of Moscow which began to emerge as the main rival to Lithuania.

Vytautas immediately gathered an army, including 5,000 Polish men commanded by Zbigniew of Brzezia and one flag of Teutonic Knights, and marched towards Russia.

The Lithuanian army was exhausted and lacked food while Russians needed to defend from an invasion of the Golden Horde, commanded by Edigu.

Švitrigaila remained imprisoned for nine years until his escape was organized by Dashko Feodorovich Ostrogski, Aleksander Nos, and Alexander of Smolensk.

The city was captured and Švitrigaila received support from local nobility, but instead of waging a war, he retreated to Wallachia.

Polish nobles understood the importance of neutralizing Švitrigaila, who continued to receive Teutonic offers for an alliance, and sent a delegation to persuade Vytautas to forgive his cousin.

In the spring of 1421, he won a battle against the Tatars; in the summer of 1422, he participated in the Gollub War and subsequent Treaty of Melno; in 1424–1426, he was sent to a diplomatic mission to Riga; he also took part in Vytautas' raid against Novgorod.

[4] This violated the terms of the Union of Horodło of 1413, where Lithuanians promised not to elect a new Grand Duke without the approval of the Kingdom of Poland.

[4] In order to receive Ruthenian votes Švitrigaila granted equal rights to Catholic and Orthodox nobles – it was one lasting achievement of his brief reign.

[5] The Polish nobility, led by Zbigniew Oleśnicki, were outraged and demanded that Švitrigaila acknowledged his fealty to his brother Jogaila, King of Poland.

Possibly Lithuanian nobles were dissatisfied with favors Švitrigaila showed to Orthodox dukes, but before the coup no such opposition manifested itself.

[4] Sigismund, who did not play a major role in Lithuanian politics before the coup[4] and who initially supported Švitrigaila,[10] became the Grand Duke and resumed policy of union with Poland.

At the age of 70 (or 85, according to some sources), he was too old to resume his struggle for the Lithuanian throne and more importantly had no support from the Council of Lords led by Jonas Goštautas, that in June 1440 elected Casimir Jagiellon, brother of Polish King Władysław III as Grand Duke.