[5][6] Having graduated from university, he was hired by the law firm Clayton Utz, from where he provided advice on energy reforms to the Department of Prime Minister and Cabinet.
[6] He would spend 14 years at the management consultancy as an analyst; first in Sydney but later in New York and Washington, D.C.[4] Reported projects included government level assignments, in North America, Asia and the Caribbean nation of Haiti.
[5] Although historically considered to be a safe Liberal seat, Labor's Jerome Laxale won the two candidate preferred count 50.98% to Kennedy's 49.02%.
Political issues surrounding the COVID-19 pandemic were still live at this time, and as Kennedy interacted with a wide spread of community groups, he indicated some libertarian preferences.
[17] Kennedy and his family moved into the community before the vote, making their home in Woolooware, then began campaigning in shops and beaches.
[19] One Sutherland Shire councillor, Jack Boyd, criticised Kennedy for not living in the community, and for being a "cosplay" Sharks supporter.
[20] Kennedy expressed that he was more interested in the cost of living challenges faced by the people of Cook, although he had to admit that he was a lifelong supporter of Canterbury Bulldogs.
[21] He had won support from several party elders in the process, including former NSW Premiers Nick Greiner and Dominic Perrottet, current state Liberal leader Mark Speakman, along with sitting federal parliamentarians Angus Taylor and Senator Dave Sharma.
[7] Conversely, Labor announced they would not contest the seat, leaving the Greens candidate Martin Moore as Kennedy's strongest opponent.