Teacher Bailey was aware he had a real talent on his hands when he persuaded the 13 year-old and his parents to consider a future with Chelsea.
And he helped seal the deal by driving Terry to training night after night and playing Diana Ross songs on his cassette player.
Bailey told The Sun: "I had a big collection of Diana Ross stuff, her solo albums and others with her Motown group The Supremes.
"John absolutely loved them, he always wanted me to put them on. But he particularly liked the slower more emotional ones. He knew all the lyrics. John can be a quiet thoughtful lad and the songs appealed to his nature.
"When you are a scout you want your players to be happy so that they feel comfortable at the club - and Diana Ross certainly kept him happy!"