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Best's mother, Mona Best (born Alice Mona Shaw), was born in Delhi, India, and was the daughter of Thomas (an Irish major) and Mary Shaw. Randolph Peter Scanland (later surnamed Best), her first child, was born in Madras (now Chennai), Madras Presidency, British India, on 24 November 1941. Best's biological father was marine engineer Donald Peter Scanland, who subsequently died during World War II. Best's mother was training to become a doctor in the service of the Red Cross when she met Johnny Best, who came from a family of sports promoters in Liverpool who ran Liverpool Stadium.

Best's family lived for a short time at the family home, "Ellerslie" in West Derby, until Best's mother fell out with her sister-in-law, Edna, who resented her brother's choice of wife. The family then moved to a small flat on Cases Street, Liverpool, but Mona Best was always looking for a large house--as she had been used to in India--instead of a smaller semi-detached house, which were prevalent in the area. After moving to 17 Queenscourt Road in 1948, where the Bests lived for nine years, Rory Best saw a large Victorian house for sale at 8 Hayman's Green in 1957 and told Mona about it. The Best family claim that Mona then pawned all her jewellery and placed a bet on Never Say Die, a horse that was ridden by Lester Piggott in the 1954 Epsom Derby; it won at 33-1 and she used her winnings to buy the house in 1957. The house had previously been owned by the West Derby Conservative Club and was unlike many other family houses in Liverpool as the house (built around 1860) was set back from the road, had 15 bedrooms and an acre of land. All the rooms were painted dark green or brown and the garden was totally overgrown. Mona later opened The Casbah Coffee Club in its large cellar. The idea for the club first came from Best, as he asked his mother for somewhere his friends could meet and listen to the popular music of the day. Best passed the eleven plus exam at Blackmoor Park primary school in West Derby, and was studying at the Liverpool Collegiate Grammar School in Shaw Street when he decided he wanted to be in a music group. Mona bought him a drum kit from Blackler's music store and Best formed his own band, the Black Jacks. Chas Newby and Bill Barlow joined the group, as did Ken Brown, but only after he had left the Quarrymen. The Black Jacks later became the resident group at the Casbah, after the Quarrymen cancelled their residency because of an argument about money. During 1960, Neil Aspinall became good friends with the young Best and subsequently rented a room in the Bests' house. During one of the extended business trips of Best's stepfather, Aspinall became romantically involved with Mona. Aspinall fathered a child by Mona: Vincent "Roag" Best, Mona's third son--who is Best's half-brother. Aspinall later became the Beatles' road manager, and denied the story for years before publicly admitting that Roag was indeed his son.
Pete Best