Socialist Party (1999–2016) Jolly ran for election to the Victorian
electoral district of Richmond as a member of the Socialist Party several times. In these elections he stood as an
independent, as the party was not registered with the
Victorian Electoral Commission. In the
1999 Victorian state election he gained 12.0% of the vote. Jolly re-contested the seat in the 2002, 2006, 2010, and 2014 state elections, with lesser success. During these elections the party campaigned for policies such as free public transport, promoting the local arts scene, and
anti-capitalism. Their 2010 campaign was supported by the CFMMEU, the
Electrical Trades Union (ETU), and the
United Firefighters Union (UFU), who raised $25,000 for the campaign.
Victorian Socialists (2018-2019) In February 2018, Jolly announced that he will be contesting a seat in the
Legislative Council in the
2018 Victorian state elections as the leading candidate of the Victorian Socialists ticket. The decision to run in the
Northern Metropolitan Region was considered controversial by
Reason Party's Fiona Patten, due to the possibility of splitting the non-conservative vote in the count for the last seat. This ticket was supported by a wide variety of trade union groups, including the ETU, the
National Union of Workers, the CFMMEU, the UFU, the
Australasian Meat Industry Employees Union, and the
Victorian Allied Health Professionals Association. The ETU secretary Troy Gray justified this support over parties such as the
Australian Labor Party, a traditional unionist party, by stating that Jolly was the only candidate representing "
blue collar values". In 2017, Jolly voted in favour of the controversial decision to cancel its Australia Day ceremony as a part of the Change the Date campaign. This resulted in backlash from the
federal government whereby the council was stripped of its citizenship powers and the council being protested by nationalist groups.
Mayor of Yarra (2024–present) In 2024 Jolly was elected as the Councillor for the Mackillop ward. Jolly ran with a grouping of independents named "Yarra for All". The grouping picked up 4 out of 9 councillors, dislodging the Greens from power. He was re-elected in November 2025 to serve as mayor for 2026. Jolly has been opposed to a new emergency services levy. The Victorian government plan would have local councils collecting the levy on behalf of the state government. He has stated that the levy would make councils "debt collectors for
Spring Street". In October 2025, Jolly was charged with assault following an alleged incident at an election afterparty in Fitzroy in November 2024. He has stated that he will contest the charge. As Mayor, Jolly has called for a
safe injecting room in Richmond to be relocated away from its current location next to a primary school. A former advocate for the facility, he called its placement "the greatest public policy disaster in recent Victorian history". Under Jolly's leadership, the City of Yarra, voted in November 2025 to end its long-term support for the room. Jolly has been critical of a
Victorian government plan to demolish public housing towers, some of which are in Yarra council's area, calling it a "land grab for developers". In testimony to a parliamentary enquiry, he stated that the plan was designed to hand over valuable real estate to construct "high-rises for rich people". Jolly, a former public housing tenant, stated that "[t]his is ethnic cleansing. This is class cleansing. If those towers go down, Fitzroy will be wall-to-wall rich people." The government stated that the towers are "past their shelf life" and "not habitable"; however, he said "Eighty per cent of private high-rise apartments in Melbourne ... don’t reach the minimum standards that have been used against the public housing towers right now as a reason for demolition". == Personal life ==