He failed to make the grade at Coventry as a right-back and then a goalkeeper.
Now Marcus Harness is plotting his home city’s downfall – as a winger.
The 23-year-old arrived at Fratton Park in the summer for a fee of around £1m, having caught the eye with some outstanding Burton displays.
Encouragingly, the attacker recorded his maiden Blues goal during a man-of-the-match showing in the Blues’ 2-1 defeat at Sunderland on Saturday.
Pompey’s next fixture is the Tuesday night visit of the Sky Blues, an encounter Harness is relishing.
Hailing from Binley, in Warwickshire, he grew up in the Coventry area, representing their youth team in two separate spells.
Now he’s facing them as a winger with an eye for goal.
He said: ‘When I was aged 13-14, I played for Coventry in goal on a Sunday and up front for Nuneaton on a Saturday!
‘The Coventry thing was a trial, I was there for a year as a goalkeeper, but didn’t sign.
‘At the same time, I was playing outfield for Nuneaton, it was a little Saturday team, it wasn’t a very good set-up.
‘In the end, I decided not to play in goal any more, I sacked it off.
‘I was all right as a keeper, but a bit small, and didn’t enjoy it as much as I do outfield.
‘Mind you, I had earlier been on Coventry’s books as a right-back, but they released me!
‘I’ve played everywhere.’
Despite Harness’ strong Coventry ties, he insists he has no affiliation with the Sky Blues.
He twice finished on the winning side against Mark Robins’ team last season, while representing Burton.
Similarly, Pompey also completed the double over the team which is now booked to arrive at Fratton Park on Tuesday evening.
And Harness is keen to savour that winning feeling once again.
He added: ‘I’m not a Cov fan, but have a special place inside for the club.
‘I know a lot of people who have played for Coventry and still play for Coventry.
‘I’ve beaten them a few times before in my career – and would love to do it again.’