Di Natale has been a Greens' Senate candidate since 2004. Di Natale also ran for the position of Lord Mayor of Melbourne in 2004, coming second to the elected John So. In both 2002 and 2006, Di Natale was narrowly defeated in the seat of Melbourne in the Victorian Legislative Assembly, almost unseating ALP health minister Bronwyn Pike. Richard received 48% of the two-party preferred vote in both elections, missing out on a win. Di Natale has acted as health spokesperson for the Greens in Victoria and in 2002 spoke about the Greens' support for harm reduction policies to manage illicit drug use. In April 2007, Di Natale spoke out about the health implications of climate change, and later that year voiced concerns about terror laws in relation to the then suspect Dr. Muhamed Haneef. Di Natale was nominated as the Australian Greens' lead senate candidate for Victoria for the 2010 federal election. Greens leader Senator Bob Brown described Di Natale as the Greens' "next strongest hope" at this election. At the 2010 election, Di Natale won a Senate seat representing Victoria. His term began on 1 July 2011. Upon taking up his seat in the Senate, Di Natale became the Greens' federal spokesperson for health. Di Natale's other portfolios include sport and multiculturalism. Di Natale was elected unopposed as parliamentary leader of the Greens party room on 6 May 2015 following the resignation of Christine Milne from the position. The Greens achieved mixed results at the 2016 Federal Election. The Party targeted several House of Representatives seats, but did not win any additional seats despite achieving large swings. The party also lost a senator. Di Natale argued that the Greens' election strategy had been successful, with voters now seeing them as a major party. On 3 February 2020, Di Natale resigned as leader of the Greens and planned to retire from politics, citing family responsibilities. Adam Bandt was elected unopposed to replace Di Natale for the leadership role.
Parliamentary career
At the 2010 federal election, the Australian Greens achieved a shared balance of power in the House of Representatives and the sole balance of power in the Senate. In the Senate, they have been in a shared balance of power position in the outcomes of the 2007 federal election and the 2013 federal election. Di Natale secured almost $5 billion towards Medicare-funded dentistry, which he described as "laying the foundations for Denticare" – the Greens' policy of universally available Medicare-funded dentistry. Di Natale campaigned against the Future Fund's holdings in tobacco funds, a campaign that was ultimately successful with the Fund divesting the entirety of its tobacco holdings in 2012. Di Natale has also helped establish Senate inquiries into a number of issues of public significance including budget cuts, medicinal cannabis, the emergence of "superbugs", hospital funding, air pollution, pharmaceutical transparency, sports science and gambling reform. Di Natale conducts ongoing campaigns for improved human rights in West Papua, timely access to cost-effective drugs through Australia's Pharmaceutical Benefits Scheme, and science-based public health policies in areas such as wind farms and vaccination policy. Di Natale was the Chair of the Senate Select Committee into the Abbott Government2014 federal budget budget cuts and Deputy Chair of the Senate Select Committee into health. He is the co-convener of the Parliamentary Friends for Drug Policy and Law Reform, the Parliamentary Friends of West Papua and the Parliamentary Friends of Medicine. On 3 February 2020, Di Natale resigned as leader of the Greens and announced an intention to resign from the senate.