His paternal grandfather, Aleksa, was an anti-Ottoman bandit leader, known as a hajduk, who was apparently assassinated at the direction of the Montenegrin king's father-in-law.
[5] During World War II, Djilas's sister Dobrinka was murdered by the Chetniks[8] and his father was killed during a battle with the Balli Kombëtar in Kosovo.
Eleven months later, having not changed his ways, Djilas was again arrested, but this time he was tortured then sentenced to three years imprisonment in the Sremska Mitrovica Prison.
While in jail he met several senior members of the Communist Party of Yugoslavia (Serbo-Croatian Latin: Komunistička partija Jugoslavije, KPJ), including Moša Pijade and Aleksandar Ranković.
[5][11] In April 1941, Axis powers Nazi Germany, Fascist Italy and the Kingdom of Hungary invaded Yugoslavia and quickly defeated her armed forces.
Yugoslavia was partitioned, and as part of this, most of modern Montenegro was subjected to military occupation by the Italians, who installed a civil commissioner.
[13] Djilas helped Josip Broz Tito to establish the Yugoslav Partisan resistance and became a guerrilla commander during the war following Germany's attack on the Soviet Union on 22 June 1941 (Operation Barbarossa) when the Communist Party of Yugoslavia's (KPJ) Central Committee decided that conditions had been created for armed struggle.
[citation needed] In early November 1941,[15] Tito dismissed Djilas from the command of Partisan forces in Montenegro because of his mistakes during the uprising, including what were called his "leftist errors".
Following the withdrawal of Supreme Commander Tito and other Party leaders to Bosnia, Djilas stayed in Nova Varoš in the Raška (on the border between Serbia and Montenegro).
Having responsibility for propaganda, he created a platform for new ideas and he launched a new journal, Nova Misao ("New Thought"), in which he published a series of articles that were increasingly freethinking.
Between October 1953 and January 1954, he wrote 19 articles (only 18 were published) for Borba, the official newspaper of the League of Communists of Yugoslavia, wherein, encouraged by Tito, he developed the Yugoslav critique of over-bureaucratic Stalinism in the Soviet Union, in favour of a shift away from central planning towards more economic autonomy.
[citation needed] On 25 December 1954, he gave an interview to The New York Times in which he characterized the situation in Yugoslavia as "totalitarian", adding that his country was ruled by "undemocratic forces" and "reactionary elements".
[22] On 19 November 1956, Djilas was arrested following his statement to Agence France Presse opposing the Yugoslav abstention in the United Nations vote condemning Soviet intervention in Hungary and his article to The New Leader magazine[23] supporting the Hungarian Revolution.
[25] In the book he argued that communism in Soviet Union and Eastern Europe was not egalitarian, and that it was establishing a new class of privileged party bureaucracy, who enjoyed material benefits from their positions.
[24] In prison, Djilas completed a massive scholarly biography of the great Montenegrin prince-poet-priest Njegoš as well as fictional novels (Montenegro) and short stories.
[citation needed] In this book, Djilas described the Šahovići massacre, a massacre of the Muslim population of the Yugoslav village of Šahovići (modern-day Tomaševo in Montenegro) and its neighboring area on 9–10 November 1924 by a mob of 2,000 Orthodox Christian men from Kolašin and Bijelo Polje who sought revenge for the earlier murder of Boško Bošković.
[27] He would be imprisoned again in April 1962 for publishing abroad Conversations with Stalin, which became another international success and which Djilas personally considered his greatest work (see Rise and Fall).
[28] For Conversations with Stalin, Djilas was sentenced in August 1962 to another five years – or fifteen, added to the earlier punishments – allegedly for having "revealed state secrets", which he denied.
[citation needed] During his internment, Djilas also translated John Milton's Paradise Lost into Serbo-Croatian by utilizing toilet paper.
"[31] Djilas was dubbed by Serbian nationalists as the "creator of the separate Montenegrin ethnicity"[This quote needs a citation] (as opposed to Serb).
In an interview with the Borba Daily on 1 May 1945, Djilas stated that "Montenegrins are of Serb origin",[This quote needs a citation] but had over time evolved into a separate nation and ethnic group.
After he left the party, Djilas denied there existed a separate Montenegrin ethnicity and national identity, especially in his books Njegoš: Poet-Prince-Bishop and Rise and Fall.
Djilas is mentioned in Saul Bellow's fiction Humboldt's Gift, where he writes about Joseph Stalin's "twelve-course all-night banquets" and the theme of boredom.