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John Jackson was born 28 September 1769 to a middle class [[Worcestershire]] family of builders who disapproved of his choice of boxing as a profession.<ref name=RS/>
In his boxing prime, Jackson stood 5'11" or 1.80
He was considered an exceptional amateur boxer prior to 1788. On 9 June 1788,
In his second bout on 12 March 1789, against John Ingleston, on a rainy day at Ingatestone, England, he lost in five rounds, in a bout lasting twenty minutes and suffered a broken leg, not entirely uncommon during the brutal English bouts of the late 18th century. His injury was likely caused by a slip from the muddy ground. Many present believed Jackson would have won the bout if not for his unfortunate accident. Likely distressed by his injury, he announced his retirement after his loss, but would return six years later in his most important win.<ref name=RS/><ref name=CBZ/>
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