The veteran striker has endured three play-off defeats during a career which took him to the Premier League.
Yet he remains a winner, with two successful promotion campaigns.
The opportunity for more glory in these twilight years saw him this summer reject remaining at Southend in favour of a Fratton Park swansong.
Tempted by the club’s ambition and drive to escape League Two, in his eyes the decision was absolutely correct.
And with nine matches remaining, the Irishman is hoping to chalk up a hat-trick of career promotions.
He said: ‘Last year I didn’t enjoy it at Southend because I felt there was no ambition from the manager (Phil Brown).
‘Personally, I felt he didn’t really give us a real chance to be there and thereabouts, I didn’t feel we worked hard enough to do what we needed to do, to get where we wanted.
‘That’s why I didn’t want to be there, I wanted to come somewhere that had ambition, that had drive, it wasn’t just going through the motions.
‘I couldn’t have picked a more perfect club.
‘I met Paul Cook a few years ago at Chesterfield, before a game against Aston Villa, and watched them play, Leam Richardson was there as well.
‘They were superb, you know, and how they worked and how he spoke about the game, it intrigued me.
‘We’d be foolish not to start thinking about promotion now. If we keep going the way we are then hopefully we’ll get promoted.
‘The sooner you get that promotion it’s the best feeling in the world.
‘You’re hoping it’s the end of April right now, but it’s not, so it’s just working towards tomorrow, which is a massive game.’
Pompey stand six points clear of fourth spot with nine matches remaining to put themselves firmly in the promotion frame.
Buoyed by recent results, they head to the Lamex Stadium on the back of three successive away victories, following three-point hauls at Carlisle, Crawley and Colchester.
Hosts Stevenage have been League Two’s in-form side of late, with eight wins from their past 10 matches.
However, the Blues have also demonstrated that consistency Hunt believes is so precious during any successful promotion campaign.
The 34-year-old added: ‘Consistency is the key, but is hard to come by in any league outside the Premier League.
‘You have to be on it every day in terms of work-rate and mentality, you can’t let up.
‘Every team has a barren spell of four, five or six games, every team in every league does it, but it’s how quickly you can get back on the wagon and go again and get the belief up.
‘We’ve a great bunch of lads here, a really, really strong core group.
‘It’s about putting the work in, making sure we all know the roles, the way we do them and how much we do.
‘But you can’t get any more consistent than here over the last seven or eight months.’