The PM likes everything to look just right
The perma-tanned and immaculately dressed Italian leader was looking forward to a polished EU presidency which he hoped would climax in a glossy ceremony in Rome and a spanking new EU treaty.
The treaty may well be signed, but barely 48 hours into his spell at the helm and the gloss is peeling fast.
Silvio Berlusconi's comparison of a heckling German politician with a Nazi camp guard has been seized upon by his many critics as evidence that the man is unfit to lead Europe.
As turmoil looms at home over the powder-keg issue of immigration and gaffes spark diplomatic crises, Mr Berlusconi's time at the top of the EU is already off to a rocky start.
Even before Mr Berlusconi made his fateful jibe on Wednesday, concerns had been raised about the image projected by an EU leader who late last month appeared to use parliament to secure him immunity from a bribery trial.
He is not, of course, the first European leader to benefit from such protection.
French President Jacques Chirac has survived a series of corruption scandals, touching on a range of issues from his grocery bills to allegations of illegal funding, by citing immunity.
But this is different, Mr Berlusconi's critics say. The issue at stake is not the principle of immunity so much as the way in which a law has been tailor-made to provide him with "impunity", they charge.
How can you say to the accession countries: you must converge, you must reform your judicial systems, you must defend press freedom, when a country like Italy is doing as it wishes
European University Institute
"It raises questions about justice and democracy when a European politician can act as if he is above the law," says Jan Zielonka, an analyst at the European University Institute in Florence.
Professor Zielonka noted that for the EU candidate countries, many of whom hope to join the EU in 2004, Mr Berlusconi's attitude to the Italian justice system was particularly breathtaking.
"How can you say to the accession countries: you must converge, you must reform your judicial systems, you must defend press freedom, when a country like Italy is doing as it wishes?"
Italian journalists have twice this year registered their frustrations with Mr Berlusconi through strike action, saying he is stifling objective reporting.
In May, the head of the European Commission Romano Prodi - who has himself not hesitated to use Nazi terminology in describing the prime minister - weighed in.
He alleged Mr Berlusconi was using public television "for his own personal goals in a way which has no precedents".
His remarks came on the heels of allegations against him by Mr Berlusconi, made during his bribery trial in Milan.
He charged that Mr Prodi - a former Italian prime minister - had agreed to sell a state-owned firm at below its market value as a "gift" to a political ally - an allegation the Commission president has denied.
Mr Prodi has nonetheless insisted that the row will not have an impact upon the Italian presidency and the key tasks that lie ahead - including agreement on a new constitution, which Italy would like to secure within the next six months.
Immigration could cause domestic rows during the Italian presidency
"It would be crazy for either of them to try to mess it up just to spite the other," says Dr Ettore Greco, Deputy Director of Italy's Institute of International Affairs.
"They both want this to work, to reflect well on the commission, the presidency, and Italy."
Nonetheless, the two are arch political rivals. Mr Prodi is seen as the only man who could unite Italy's divided left in the next general elections, and as such poses a direct threat to Mr Berlusconi.
As he watched the Italian prime minister dig his hole on Wednesday, some journalists reported a wry smile crossing the lips of the Commission president.
On top of the rivalries and diplomatic dilemmas, Mr Berlusconi faces some serious problems at home over the next six months.
The far-right Northern League, a member of Mr Berlusconi's own coalition, has threatened to pull out of the government if it does not get its way on immigration curbs and extensive devolution.
Mr Prodi has an eye on his return to Italian politics
The movement's anti-Europe leader Umberto Bossi had no qualms in bringing down Mr Berlusconi's first government in 1994.
Even if the government does not collapse this time, there is little doubt that Mr Bossi will prove an embarrassment to the Italian leader.
He frequently attacks senior government figures, the left, immigrants, gay people - and, not least, the EU.