Alexey Petrov, a former secret agent and government adviser on the fight against organized crime in Bulgaria, was killed in broad daylight in the company of a woman.
Petrov had escaped previous assassination attempts on him, authorities said.
Interior Ministry officials told reporters that Petrov was walking with a woman when he was shot dead, while the woman was wounded.
There were two previous assassination attempts, one in 2002 when he was allegedly injured during a drug war, and an attack in 2015, from which he escaped unharmed.
In recent years, the 61-year-old ran one of the largest insurance companies in the country. He has also served as an advisor to the head of the State National Security Agency.
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