[1] Ruprecht made his foray into politics by seeking the Liberal Party of Canada's nomination in the federal Parkdale electoral district, for the 16 October 1978 by-election.

[4] His mayoral campaign meant that he would not seek re-election in his Ward 2 seat, in the Parkdale and Brockton part of Toronto's west-end.

[10][11] The Liberals formed government after the election, and on 26 June 1985, Ruprecht was appointed as a minister without portfolio responsible for Disabled Persons and Multiculturalism.

[12] In 1996, Ruprecht was the only Liberal MPP outside of Ottawa to support Dalton McGuinty's bid for party leader prior to the actual leadership convention.

[15] Ruprecht initially planned to run in the newly created Parkdale—High Park constituency in the 1999 provincial election, but stood aside for star candidate Gerard Kennedy.

He was not appointed as the Liberal candidate, as he had to defeat human-rights lawyer Rocco Galati, at a nomination meeting on 21 July 1998, before he could run in the election.

[17] There was a controversy over the nomination process, and Galati unsuccessfully sued the Liberal party, the constituency association, and Ruprecht.

[18] Ruprecht's main opponent in the 1999 campaign was another displaced incumbent MPP, the NDP's deputy leader, Tony Silipo.

[22] The Progressive Conservatives managed to lose all their seats in the old city of Toronto, but nevertheless, won the provincial election, and Ruprecht remained in opposition.

[1] In April 2006, Ruprecht was criticized for being absent from the Ontario legislature for extended periods of time while vacationing in Cuba.

[24] He defended these trips saying he was travelling to the island to receive lessons in Spanish and Portuguese in order to better be able to communicate with his constituents.