Walton-born Jackson was an outside-right who was on Arsenal's books as an amateur before moving on to Leyton Orient where he won the admiration of many clubs for creating a number of goals for the struggling third division south club. He was signed by Liverpool in November 1951 when he was still only 18 years old. He was in the Army at the time doing his national service in Hampshire but his commanding officer granted his release to Liverpool. The Reds had been on his trail for some time but Leyton Orient were unwilling to do business without finding an adequate replacement hence Liverpool reserve Donald Woan moved in the opposite direction with an additional £6,500 paid to Orient. Jackson scored on his Liverpool debut against Bolton Wanderers but that was the only time he hit the net in the 15 league games he played that season. Although Jackson was very much part of the Liverpool squad of the time, he never really became a firm 'regular' in the side, with 27 being the highest number of league appearances he made in any single season, 1953/54.