It is a decision which has left fans angered, and somewhat bemused, as well as upset about what has been, and what could have been for Hartlepool under Challinor.
The events over the last 72-hours in particular have been as confusing as they have been disappointing from a Hartlepool perspective as Challinor looks set to drop out of the Football League despite having worked so hard to finally get a shot at it in the first place.
But while feelings are understandably raw and unclear now, and may well be for some time until Challinor portrays his side of events, Pools fans are left scratching their heads and searching for answers as to why it got this far for Challinor to seemingly throw the towel in on their club.
While Challinor has enjoyed almost unanimous success at Victoria Park since his arrival almost two years ago, there have been certain events in recent months which could have led to the 46-year-old’s desire to leave the North East.
Challinor will always be remembered for the scenes which unfolded in Bristol at the climax of last season when coming through that dramatic penalty shootout against Torquay United, and having agreed a new three year deal at the club as recently as September, supporters can be forgiven for thinking there are more elements in play as to why he has now decided to go against his signature on the dotted line.
It is a decision which will ultimately tarnish his legacy with the club. A legacy where he could seemingly do no wrong in the supporters’ eyes.
But from that very promotion final success in itself, issues have emerged for Challinor.
And whether those issues were to remain a concern for him moving forward with the club is open for debate.
Here at The Mail though, we try to make sense of why Challinor has arrived at this crossroads in his managerial career and look at some of the events which have happened in recent months which may have led to his frustration, and ultimately his decision to leave Victoria Park.
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1. Pools quick turnaround
No Hartlepool fan will ever forget that day at Bristol City’s Ashton Gate stadium, nor will Challinor who recently admitted to having lost count to the number of times he has re-watched the promotion final success over Torquay United. But amidst the ecstasy, promotion back to the Football League gave Pools and Challinor just seven weeks to prepare for the new season and while it was a consequence everybody was willing to accept, it led to a turbulent summer for Challinor as he struggled to tie down some of his players to new deals and likewise struggled to bring in any fresh faces away from trialists. (Photo by Harry Trump/Getty Images) Photo: Harry Trump
2. Armstrong joins Harrogate Town
One of those players Challinor struggled to tie down was forward Luke Armstrong. The North East native may not have been a Pools player to try and strike out terms with given his loan status from Salford City, but Challinor admitted to not being given the opportunity to try and bring Armstrong back to the club on a permanent basis with the 25-year-old agreeing to sign for League Two rivals Harrogate Town just days after starring in the promotion final. It was a blow to Challinor who was losing one of his prized assets having scored 15 goals in their promotion winning campaign. (Credit: Mark Fletcher | MI News) Photo: Mark Fletcher
3. Oates joins Mansfield Town
But two weeks later things would get worse for Challinor as he would lose the second of his dynamic forward duo in Rhys Oates who signed for Mansfield Town. Oates enjoyed a remarkable second season at Victoria Park scoring 18 times as he led Pools’ charge to the promotion final. Oates’ desire to move left a bitter taste in Challinor’s mouth with the 46-year-old saying: “He wasn't willing to back himself and has decided his future lies elsewhere. Everyone has decisions to make that suit themselves and their circumstances which we all completely understand. The only slight disappointment from our side of things is the fact Rhys has had no communication with any staff to let us know his thoughts and decision and that leaves a bit of a sour taste. We've had other players move on who have done so in what I would say is the right way.” Suddenly, Challinor had lost his two top goalscorers just one month before the League Two season would kick-off. Picture by FRANK REID Photo: Frank Reid
4. Spennymoor defeat angers Challinor
Such a quick turnaround from the climax of the National League season to the beginning of the League Two campaign meant pre-season became something of an afterthought with localised fixtures against lower league teams all Pools were faced with to head into the new season. The first of those came at the Brewery Field against National League North side Spennymoor Town, who beat Pools fairly comfortably leaving Challinor less than impressed. “It doesn’t make a difference if it’s pre-season, it’s about winning football matches,” he said before suggesting the performance told him a lot about some of his squad. Picture by FRANK REID Photo: Frank Reid