After the 1917 February Revolution overthrew the Tsarist monarchy, the Ukrainian People's Republic was proclaimed and Petliura was elected head of its military.

During the Civil War, the UNA were responsible for the deaths of tens of thousands of Jewish civilians, and Petliura's role in the pogroms has been a topic of dispute.

His father, a Poltava city resident, had owned a transportation business; his mother was a daughter of an Orthodox hieromonk (priest-monk).

In December 1903 he was arrested for organizing a RUP branch in Yekaterinodar and for publishing inflammatory anti-tsarist articles in the Ukrainian press outside of Imperial Russia (in Austrian-controlled Lemberg, currently named Lviv, in Galicia).

At the end of 1905, after an nationwide amnesty was declared by the authorities, Petliura returned briefly to Kyiv, but soon moved to the Russian capital of Petersburg in order to publish the socialist-democratic monthly magazine Vil’na Ukrayina ("Free Ukraine") along with Prokip Poniatenko [uk] and Mykola Porsh.

[5] After Russian censors closed this magazine in July 1905, he moved back to Kyiv where he worked for the newspaper Rada [uk] ("The Council").

As the editor of numerous journals and newspapers, Petliura published over 15,000 critical articles, reviews, stories and poems under an estimated 120 noms-de-plume.

Disagreeing with the politics of the then chairman of the General Secretariat Volodymyr Vynnychenko, Petliura left the government and became the head of the Haydamaky Kish [uk], a military formation of Sloboda Ukraine (in Kharkiv).

After the April 1918 Ukrainian coup d'état, Pavlo Skoropadskyi's government arrested Petliura and incarcerated him for four months in Bila Tserkva.

With the outbreak of hostilities between Ukraine and Soviet Russia in January 1919, and with Vynnychenko's emigration, Petliura ultimately became the leading figure in the Directorate.

During the course of the year, Petliura continued to defend the fledgling republic against incursions by the Bolsheviks, Anton Denikin's White Russians, and the Romanian-Polish troops.

In April 1920, as head of the Ukrainian People's Republic, he signed an alliance in Warsaw with the Polish government, agreeing to a border on the River Zbruch and recognizing Poland's right to Galicia in exchange for military aid in overthrowing the Bolshevik régime.

Polish forces, reinforced by Petliura's remaining troops (some two divisions), attacked Kyiv on 7 May 1920, in what proved a turning point of the 1919–21 Polish-Bolshevik war.

Protected by several Polish friends and colleagues, such as Henryk Józewski, with the establishment of the Soviet Union on 30 December 1922, Petliura, in late 1923 left Poland for Budapest, then Vienna, Geneva and finally settled in Paris in early 1924.

One of the concerts by the Capella inspired George Gershwin to write "Summertime", based on the lullaby "Oi Khodyt Son Kolo Vikon"[8] All three musicians later emigrated to the United States.

He launched the weekly Tryzub, and continued to edit and write numerous articles under various pen names with an emphasis on questions dealing with national oppression in Ukraine.

In 1969, the journal Jewish Social Studies published two opposing views regarding Petliura's responsibility in pogroms against Jews during his reign over Ukraine, by scholars Taras Hunczak[23] and Zosa Szajkowski.

[25] According to Hunczak, Petliura actively sought to halt anti-Jewish violence on numerous occasions, introducing capital punishment for carrying out pogroms.

[26][27] Conversely, he is also accused of not having done enough to stop the pogroms[20] and being afraid to punish officers and soldiers engaged in crimes against Jews for fear of losing their support.

[28][29][page needed] On 25 May 1926, at 14:12, by the Gibert bookstore, Petliura was walking on Rue Racine near Boulevard Saint-Michel of the Latin Quarter in Paris and was approached by Sholem Schwarzbard.

The Jewish Telegraphic Agency reported on 27 May 1926 that Petliura's "pogrom bands" were responsible for killing tens of thousands of Jews.

[34][19][36][37] It is claimed that in March 1926, Vlas Chubar (Chairman of the Council of People's Commissars of Ukraine), in a speech given in Kharkiv and repeated in Moscow, warned of the danger Petliura represented to Soviet power.

[39] To mark the 80th anniversary of his assassination, a twelve-volume edition of his writings, including articles, letters and historic documents, has been published in Kyiv by Taras Shevchenko University and the State Archive of Ukraine.

[44] A nephew of Symon Petliura, Stepan Skrypnyk, became Patriarch Mstyslav of the Ukrainian Autocephalous Orthodox Church on 6 June 1990.

[47] During the revolution Petliura became the subject of numerous folk songs, primarily as a hero calling for his people to unite against foreign oppression.

In the songs Petliura is depicted as a soldier, in a manner similar to Robin Hood, mocking Skoropadsky and the Bolshevik Red Guard.

The blind kobzars Pavlo Hashchenko and Ivan Kuchuhura Kucherenko composed a duma (epic poem) in memory of Symon Petliura.

This duma became popular among the kobzars of left-bank Ukraine and was sung also by Stepan Pasiuha, Petro Drevchenko, Bohushchenko, and Chumak.

A number of plays such as The Republic on Wheels by Yakov Mamontov and the opera Shchors by Boris Liatoshinsky and Arsenal by Heorhiy Maiboroda portray Petliura in a negative light, as a lackey who sold out Western Ukraine to Poland, often using the very same melodies which had become popular during the fight for Ukrainian Independence in 1918.

Petliura continues to be portrayed by the Ukrainian people in its folk songs in a manner similar to Taras Shevchenko and Bohdan Khmelnytsky.