Diamond's criminal career began in 1912 when she was cautioned, along with Mary Austin, who would later marry north London racing gangster Frederick Sabini, for stealing chocolate. A number of convictions for theft followed and in 1915 she was named by police and newspapers as Queen of the Forty Thieves, successor to Mary 'Polly' Carr, who had previously held the title.
Diamond had taken over leadership of a large and expert gang of organised shoplifters. She was a skillful organiser of large expeditions across the West End of London and spread her enterprise to the provinces when London became 'hot'. Her chief lieutenant was volatile and violent Maggie Hill, born Margaret Lily Hill into a criminal north London family that one day would produce Billy Hill, dubbed 'Boss of Britain's Underworld'
Although Diamond, Margaret Hill and other Elephants served prison terms, they believed the risk was worth it - the alternative being a life of poverty. The gang was known for its stylish dress and wild partying. They could 'put on the posh' and take goods valued at hundreds of pounds from prestigious stores by using specialist garments and clever distraction techniques. Their favourite plunder was fur coats and bolts of silk which were expensive commodities between the World Wars. They were known to drive fast cars and could be violent when confronted. Alice Diamond was over five-foot eight-inches in height at a time when the average height for a man was five-foot six-inches. She wore diamond rings on the fingers of both hands and could deliver a punch a man would have envied. Another of the Forty Elephants was Lilian Goldstein, née Kendall, who was also a driver for smash and grab raider Ruby Sparks, tagged by press and police as 'The Bobbed-Haired Bandit.'
Shirley Sally Pitts, later Shirley Sally Hawkins (24 November 1934 – 16 March 1992), was an English fraudster and thief known as the "queen of shoplifters". Born into poverty and crime, she began to steal as a child to feed her siblings. She was educated in shoplifting by the Forty Elephants, also known as the Forty Thieves, and later diversified into other non-violent crime such as fraud.