He served as the Minister without Portfolio in charge of the National Investment Plan in the 2007–2008 Cabinet of Serbia and prior to that as the director of the People's Office of the President between 2004 and 2007.

Simultaneously, Đilas was active in opposing the rule of Slobodan Milošević, leading the student protests in 1991 and 1992.

As a student leader/activist, in June 1992, Đilas appeared on RTS interview programme Razgovor s povodom thus getting 50 minutes of air time on state television, which he used to further criticize Milošević's policies.

He has a minority stake in a limited-liability company called Multikom Group whose ownership is divided between Đilas (25%), Dragoslav Ilić (42%), Milica Delević (25%) and Nebojša Garić (8%).

On October 1, 2004, Đilas became the director of the People's Office, instituted by the newly elected President of Serbia Boris Tadić.

Đilas stayed in the position until May 2007 when the new Government of Serbia was finally formed by the DS and the DSS-NS coalition almost 5 months after January 2007 parliamentary election.

Đilas' time in office was marked by frequent vicious clashes with the government colleague Minister for Capital Investment Velimir Ilić.

It didn't take long for their feud to reignite and in October 2007 things boiled over when Ilić placed an angry, obscenity-laced phone call to Đilas' office, the transcript of which ended up in Serbian media.

During the 2008 Belgrade mayoral election campaign, Đilas was often denounced as a "tycoon" by the Liberal Democratic Party due to his amassed personal wealth.

He was dismissed as mayor on 18 November 2013 and Siniša Mali was appointed as president of the Temporary Council of Belgrade.

[4] After Belgrade City Council elections in 2018 when his list won 18.93% of the popular vote, Đilas announced a formation of a new opposition political alliance – as a counterweight to ruling SNS.

[5] Since Đilas welcomed Dveri (a right wing political party) into the alliance, some liberal and left leaning organizations (notably Saša Janković's PSG) refused to take part in the alliance, though they stated they are willing to cooperate on various subjects, especially on the matter of election organization.

[23] In September 2019, Đilas told the media that his party's plan for the reconciliation process of Serbs and Albanians envisions that people who committed war crimes or incited war crimes cannot participate in the reconciliation process,[24] while in October 2019 he said "I would never sign an agreement recognizing Kosovo's independence, which is against our laws, international law and contrary to concepts such as morality and the part I still believe in.

[26] Đilas is the founder and vice president of Naša Srbija humanitarian organisation for Serbian children who were left without one or both parents in the wars in the former Yugoslavia.