Yip Kai-foon who was re-captured in a hail of bullets in 1996 after years on the run, was a symbol of a more violent time in Hong Kong, which was rife with triad gangs -- organised Chinese criminal networks steeped in murky traditions and violent histories.
Images of him and his gang holding AK-47 rifles while wearing balaclavas wreaking havoc on the streets and leaving police vans and store windows riddled with bullet holes once dominated the evening news.
Yip reportedly started down his path of violent crime at the age of 19, spreading fear, and robbing gold shops, which were considered some of the most dangerous places in the city.
He and his gang were known for stealing millions of Hong Kong dollars in merchandise per heist and spraying bullets at police as they made their getaway.
He was 55 when he died in the early hours of today, a government statement said, without naming Yip.
"During hospitalisation, his condition deteriorated and he was certified dead" today the statement said, adding he was serving his term for illegal possession of arms and ammunition and escape from legal custody.
His criminal exploits were portrayed in crime drama Trivisa which won best picture at this month's Hong Kong Film Awards.
The gangster was initially jailed in 1985 but made a daring escape from a hospital while he was receiving treatment, reportedly threatening a guard with a broken glass bottle and later hijacking a van in 1989.
Yip and his gang spread terror on the streets again until he was recaptured and jailed for 41 years after a 1996 shootout with police where he was shot in the back and paralysed from the waist down.
Ahead of his arrest, authorities had offered the then- highest reward in the city of 1 million Hong Kong dollars(USD 130,000 at the time) for his capture.
He was a known associate of crime boss Cheung Tze-keung, who kidnapped the eldest son of the city's richest man Li Ka- shing and was sentenced to death in China in the late 1990s.
While Hong Kong is now considered one of the safest in the world, organised crime still stalks the city, with the continued presence of gangs - including Wo Shing Wo, 14K and Sun Yee On - spreading their activities to southern China and further overseas.
(This story has not been edited by Business Standard staff and is auto-generated from a syndicated feed.)