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First elected to city council in 1994 he was one of the more right leaning members of city council aligned with mayor Mel Lastman. Of Portuguese background, Silva is popular locally for his help with immigration matters.
Silva's move to federal politics was not without controversy, however, as it saw him claim the Liberal nomination in Davenport instead of popular Liberal incumbent Charles Caccia in a process that saw widespread allegations of unfairness. An ally of new Prime Minister Paul Martin, Silva was seen by the party machinery as a preferable candidate to Caccia, the longest serving MP in parliament, whose leftist and strongly pro-environment views clashed with the direction Martin wished to move the party. Silva signed up enough new members to likely defeat Caccia in a nomination battle; Caccia instead chose not to file to be the party's candidate, and after mulling running in the election against Silva as a Green candidate or as an Independent, announced his retirement from politics. Despite much ill will in the riding towards the ousting of Caccia, Silva still won the traditionally Liberal seat by a convincing margin.
Shortly after the election, Silva came out as gay in a Toronto Star profile. Ironically, it has been alleged that some of Silva's campaign workers made homophobic slurs against NDP candidate Rui Pires in order to sway voters to Silva, although these claims have not yet been proven.