The billionaire tycoon, who was convicted last year and has been expelled from parliament, has been ordered to work once a week for up to a year as a volunteer in a hospice for Alzheimer's patients near Milan.
"To prison!" a trade unionist protester in a clown hat shouted, as Berlusconi arrived at the clinic with his security detail in a chauffeur-driven car, wearing a blue suit with an Italian flag badge.
The Catholic Church-run hospice in Cesano Boscone has said it will not allow Berlusconi to use his stint for political grandstanding in front of the world's media and will treat him like any other volunteer.
The disgraced politico has dominated Italian politics for two decades and is leading a campaign for European Parliament elections despite being barred from running and his party is expected to get 20 percent of the vote.
Massimo Restelli, head of the hospice's care services, told the La Repubblica daily that Berlusconi's introduction would be "gradual" so that he and the elderly patients can get used to each other.
"We ask everyone including Berlusconi to observe, to listen and not to get performance anxiety," he said, adding that the media magnate would be accompanied at all times by a medical worker specialised in Alzheimer's.
"We'll see if Berlusconi's presence creates some kind of close bond, if he is a reference for anyone. The guests do remember things, even if that seems absurd to people who do not know the illness," he said.
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