The present democracy in the world that arguably come the closest to match Baudrillard’s theory of the transpolitical is perhaps the Republic of Italy under the Presidency of Silvio Berlusconi. Berlusconi’s three periods in Office (1994-1995; 2001-2006; and 2008-2011) makes him the longest serving post-war Prime Minister of Italy. Simultaneously, Berlusconi has had an extensive record of criminal allegations directed at him, involving mafia collusion, false accounting, tax fraud, corruption and bribery of police officers and judges. In spite of being tried in Italian courts in several cases, Berlusconi has not been found guilty, except that of providing a false testimony in 1990. In addition, the many controversies and scandals home and abroad surrounding his presidency have left many foreign political commentators flabbergasted over his seemingly continuous popularity among the Italian voters. Berlusconi is often referred to as an ‘enigma’ or ‘phenomenon’ (cf. Hewitt, 2010). Hence, traditional representative democracy theory seems to struggle to explain the success of an archetypal demagogue like Berlusconi among enlightened and educated voters. Furthermore, Baudrillard’s possibly preferential choice of medium – the television screen – continues to have a unique standing in Italian society. 80 percentage of Italians use it as their main medium of information (Gandini, 2009), and Italy has been relatively slow in updating to Internet based communication. For instance they lag behind the European average in offering its inhabitants Broadband Internet access, partly because of an outdated Italian phone network. There is also a shared understanding that Italy for centuries has been a society of the spectacle (Perniola, 1995), in which imagery has had an unusual penetrative power over the Italian public. For instance, Simonetta Falasca-Zamponi (2000) analysis of Mussolini and the National Fascist Party’s rise to power demonstrates how an aesthetical approach to politics was the vital key behind fascism’s influence.