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Vitali Klitschko began campaigning for mayor of Kiev shortly after his retirement in 2005. He lost the 2006 mayoral election to Leonid Chernovetskyi but placed second with 26% of the vote, ahead of the incumbent Oleksandr Omelchenko.

Vitali Klitschko campaigned on an anti-corruption platform associated with Pora party. Analysts stated his relatively late entry into the campaign might have cost him votes. Still, he was elected as a people's deputy to the Kiev City Council.

In the May 2008 Kiev local election he ran again and won 18% of the vote. His party, Vitaliy Klychko Bloc, won 10.61% of the votes and 15 seats and again he was elected into the Kiev City Council. His campaign hired Rudy Giuliani as a consultant for the campaign. In 2008 Vitali Klitschko was also appointed to the Ukrainian delegation of the Congress of the Council of Europe. 

Klitschko became the leader of the political party Ukrainian Democratic Alliance for Reform in April 2010. During the 2010 Ukrainian local elections the party won representatives in (Ukrainian) municipalities and Oblast Councils (regional parliaments).
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