Alex Hay has had a foot in both camps during his career and is torn over which way this weekend's derby between Chester FC and Tranmere Rovers will go.
His head tells him Rovers, the club where he came through the youth system before making 50 first-team appearances, have the experience and class to grind out the victory needed to move back into the play-off places.
However, he is wary of writing off an unpredictable Blues side, particularly one that has a habit of pulling the occasional rabbit out of the hat when it's least expected.
Pressed for a prediction, Hay, now working as chief scout for National League North outfit AFC Fylde, forecasts a narrow 2-1 win for Gary Brabin's men but admits he will not be surprised if he is proven wrong.
"It's going to be an interesting game because I think all of the pressure is on Tranmere even though Chester are at home," said Hay.
"You look at the teams and form and you would expect them to win but Chester are dangerous because this season they've produced performances here and there where it's not been expected.
"Chester didn't play well in the first game at Prenton Park but I think in front of their own fans and with a big crowd behind them they'll go at Tranmere.
"I think it'll be a Tranmere win and it'll finish 2-1. That will probably get me lynched next time I go back to Chester but if I had to stick my neck out then that's how I see it."
Hay spent three years at Chester as part of Neil Young's backroom team and as chief scout was part of the Evo-Stik League Premier Division and Conference North title-winning campaigns.
The ex-Cammell Lairds manager, who had spells at Rushden & Diamonds, Bangor City and Rhyl as a player, departed the Lookers Vauxhall Stadium when offered the chance to return to Prenton Park in the same role.
But the likeable 34-year-old has been frequent visitor to Chester over the past couple of seasons and can understand the frustrations at a campaign in which fans hoped to better last term's 12th place finish.
Hay said: "I think last season there was a surprise element to Chester in how attacking the side was. They went out and looked to score more goals than the opposition every week and that brought them some good results.
"This season that surprise factor has gone and other teams are better prepared for them but at the same time they've been very inconsistent because they'll have a good win and then go on a poor run but when the mood starts to turn a bit negative they'll produce a good performance and get a win when it wasn't expected.
"Ross Hannah is the obvious stand-out because to score as many goals as he has in a side that has been struggling a little bit is fantastic. He's been a very good striker at this level for a while and I think the number of goals he's scored will have been noticed at some of the bigger clubs.
"There's quite a lot of lads I know there still and even thought he's been out of the side in recent weeks I still think Ian Sharps can be very important for them with his experience at the back. John Rooney can be a big influence in midfield and chips in with some goals from central midfield and I know Mahony (Craig Mahon) hasn't got quite as many this season but again he can be a threat."
Hay returned to Tranmere in June 2014 as chief following Rob Edwards' appointment as manager. Edwards was sacked two months later with Micky Adams taking over and Hay himself departed in November, explaining he felt the scouting role demanded a full-time focus.
Adams departed via mutual consent in April 2015 with the club heading out of the Football League and relegation was confirmed a week later.
Ex-Chester City midfielder Brabin took charge in the summer and assembled a new squad, one which has improved as the season has progressed and now finds itself on the edge of the play-offs.
Hay believes pre-season talk of title challenges was over-ambitious in such a competition league, however he expects Rovers to finish the top-five and have a shot at an instant return to the Football League.
He said: "It's been tough for them because of the expectation and it's a very difficult division. There's only one automatic promotion place and I always thought that would be beyond them but I did think the play-offs would be in reach.
"It's a long season because you're playing Saturday and Tuesday most weeks so a week is a long time in that division because if you win two or three games in a row you can shoot up the table.
"Over the last few weeks Tranmere have started to keep a lot of clean sheets and have hit on something defensively which makes them hard to beat. They've had a few too many draws in games they probably should have won because they've not been taking chances.
"Apart from James Norwood they haven't really had anyone putting the ball in the net on a consistent basis so ideally they need someone else to go on a bit of a scoring run.
"It's taken them a bit of time to bed in and the squad has changed over the season but they have been within touching distance for most of the season and now they are well in the mix and even though a few teams below them have got games in hand I expect them to go and make the play-offs."