Bailey grew up in the Cassava Piece area of Kingston, Jamaica. He played for the Phoenix All-Star Academy operated by his adoptive father, Craig Butler. In 2011, Butler arrived in Europe to find a club for Bailey and Butler’s biological son, Kyle. They wandered around Austria, Germany and Holland, before ending up in KRC Genk, where Bailey went on trial in the beginning of 2012. Genk was convinced of his qualities, but because of the very strict regulations on minors by FIFA, they couldn't offer him a contract. So, the club made Leon Bailey sign a draft agreement when he was only 15 years old, which is illegal in Belgium. Bailey moved into a house in As, near Genk. After Butler left for Mexico, initially to formalize his move to Belgium, he went missing for four months. In these four months Genk took care of the minor children, who at that time were without parents or a legal guardian illegally residing in Belgium. When Butler returned after four months, KRC Genk offered him a job with a sponsor of the club. This was the only way to try and bend FIFA rules on minors. After the Labour Ministry heard of the matter, they raided KRC Genk, and Butler and his players had to retreat. So, he went to Standard Liege, but the transfer wasn't approved because Butler had no work permit. As a result, they could not legally reside in Belgium. Thereafter they went back to Jamaica, but they returned several times to Europe, where Butler offered his players at several European clubs. With AFC Ajax, he reached a verbal agreement in October 2013, but a transfer did not materialize. The FIFA rules did not permit a player under eighteen years to sign a professional contract with a football club. In the beginning of 2015, Bailey appeared in AS Trenčín, where he signed a contract.
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