 Before their arrival, Hartlepools had been forced to apply for re-election to the Football League six times in the previous seven years, and Taylor stated that the squad were all free transfer signings and some of the players struggled with "drink, debt or abandoned wives". The two gradually turned around the club's fortunes, and started by painting Victoria Park. Taylor had little chance to show his skills in the transfer market as the club only had £ 7,500 to spend, £ 4,000 of which went on centre-half Johnny Gill. Other signings included two of Taylor's former players at Burton, defender Tony Parry and goalkeeper Les Green; Parry would go on to win the club's Player of the Year award. The pair went on to lead the club to an eighth-place finish in the Fourth Division in 1966 – 67 after replacing most of the playing staff, an improvement on 1965 – 66 when the pair had only managed an 18th-place finish. Clough had initially wanted to quit the club numerous times due to interference from chairman Ernest Ord, but Taylor insisted that they stay as they could not walk out on their first job in management. After Ord resigned as chairman Clough wanted to remain at Hartlepools, but Taylor persuaded him to take the offer to manage Derby.
