ɪn nˈaɪntiːnhˈʌndɹɪd nˈaɪnti nˈaɪn, kˈɛnədi dʒˈɔɪnd tɚɹˈɑːntoʊ sˈɪɾi kˈaʊnsɪlɚɹ ɑːlˈɪviə tʃˈaʊz tˈiːm æt sˈɪɾi hˈɔːl, æz kənstˈɪtʃuːənsi ɐsˈɪstənt ɪn wˈɔːɹd twˈɛnti.
In 1999, Kennedy joined Toronto City Councillor Olivia Chow's team at City Hall, as constituency assistant in Ward 20.