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MILAN—Mafia ‘boss of bosses’ Salvatore ‘Toto’ Riina, who was serving 26 life sentences as the mastermind of a bloody strategy to assassinate both rivals and Italian prosecutors and law enforcement trying to bring down Cosa Nostra, died early Friday.

Riina died the day after his 87th birthday and hours after the Justice Ministry had agreed to allow family members at his bedside. He had been in a medically induced coma following two surgeries in recent weeks in the prison wing of a hospital in Parma, northern Italy. The ministry, without elaboration, confirmed his death.

Riina, one of Sicily’s most notorious Mafia bosses who ruthlessly directed the mob’s criminal empire during 23 years in hiding, was serving the life sentences for multiple murder convictions, some dating back to the 1950s.

“He was still considered the ‘boss of bosses,’ even in prison,” Roberti told the AP in a phone interview. “His death will lead to a power struggle at the top of the Cosa Nostra” even if during his decades in a Milan prison cell severe restrictions on his contacts ensured he no longer had any operational influence.