Giuseppe Mastini, 60, who was given a life sentence in 1989, took advantage of a temporary release from a high-security jail in Sardinia to flee, failing to return to his cell on Saturday, the Polizia Equilibrio e Sicurezza (ES Polizia) union said.
Police have since launched a nationwide manhunt.
Originally from Bergamo in northern Italy, Mastini moved to Rome in the 1970s with his family where he committed his first murder aged 15, killing a tram driver during a bungled robbery.
Nicknamed “Johnny the Gypsy” because of his Sinti origins, Mastini terrorised Rome during the 1970s and 1980s with crimes including murder, kidnapping and burglary.
He was also briefly investigated for involvement in the death of the Italian film director Pier Paolo Pasolini in 1975, which he has denied.
He first escaped from jail in 1987, when he failed to show up after a temporary release from prison.
While on the run, he committed robberies, murdered a police officer, injured another and took a young girl hostage.
After being caught and jailed again, he was given another temporary release in 2014 which was filled with “irregularities”, ES Polizia said, although it was unclear whether he actually escaped that time round.
But in June 2017, he once again escaped from Fossano prison in Piedmont, following the same method.
Police unions expressed anger over Mastini’s latest escape.
“In 2014, after being awarded a day release permit, he showed he was responsible for irregularities and in 2017 he did exactly the same thing,” Vincenzo Chianese, the president of ES Polizia, told Italian media.
“The legislation that enables people, who should clearly not be allowed to leave prison, to do so, must absolutely be changed.
“Not only to prevent families of victims having to be warned every time this happens, thus renewing their pain, but also because the feeling of impunity in our country deeply undermines the credibility of the state.”
With ANSA