John Askey spent almost his entire playing career as a forward for Macclesfield Town, clocking up well over 600 appearances for the Silkmen over the course of 19 seasons, and scoring over 150 goals. He was named as the club's all-time greatest player by the supporters, and was awarded the freedom of the town in 2018. On retiring from playing it was no surprise to see Askey remain at Moss Rose as part of the coaching staff. He had a brief spell managing the first team in 2003/04 followed by a longer one a decade later. He led the Silkmen to three consecutive top ten finishes in the National League before leading them to the title in 2018, at which point he finally left the club to join Shrewsbury. That job proved to be short-lived but he soon found employment again, spending two years at Port Vale, before joining York City. Askey clinched the second promotion of his management career in 2022 when he led York to promotion from National League North via the playoffs. He was surprisingly dismissed later that same year with the Minstermen a comfortable 12th in the National League table. Pools were in perilous relegation trouble in the Football League's basement division in February 2023. Keith Curle became the club's second managerial casualty of a difficult season when he was dismissed with just 13 games to go. Askey was handed the tough task of keeping Pools in the Football League just two years after rejoining it.