We know that Silvio Berlusconi is a very rich man and controls the media in Italy.
What are the "political factors" that put him on top of the politics chain in Italy?
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His first government was not stable and fell in less than a year, so it is arguable that his media empire was little help in that instance…
His second government though, has been the longest serving Italian cabinet post WWII. This is due, in first instance, to the political stability of his alliance.
On the other hand the government fell at the end of legislature with less electoral favour than at the beginning:
House of Freedoms did not do as well in the 2003 local elections as it did in the 2001 national elections. In common with many other European governing groups, in the 2004 elections of the European Parliament, gaining 43.37% support. Forza Italia's support was also reduced from 29.5% to 21.0% (in the 1999 European elections Forza Italia had 25.2%).
So one could argue that he has not been on top of Italian politics, but merely one of the prominent figures. On the other hand, it is a well know fact that Berlusconi's media, such as one of his newspaper, orchestrated campaigns to "hit" perceived political enemies. One of the most notorious examples is the case of Emma Marcegaglia, where her company group would be targeted by the newspaper after she spoke against Berlusconi.
The reasons of his success in Italian politics lie probably in his character and ability as a media person, a salesman and a media magnate. He clearly knows how to manipulate the media, and he is clearly a strong leader that people like to follow. Both these are strong reasons behind his success, but also in the entrepreneurial arena.