As Wycombe boss, he suffered Andy Barcham rejection.
Now Gary Waddock finally has the flying winger at his training-ground disposal.
And he’s relishing trying to coax the best out of the former Gillingham player he regards so highly.
It was the summer of 2011 when the Chairboys were rivalling Scunthorpe for the signature of free agent Barcham.
The outcome was instead a move to their League One rivals on a two-year deal to leave Waddock empty-handed.
Some three-a-half years later their paths have crossed once again, only they now find themselves at the same football club.
Waddock’s December arrival as assistant manager has matched him up with the 28-year-old he clearly rates.
Andy Awford has since named Barcham in the starting line-up for three of Pompey’s last four matches following a wretched 2014 blighted by injury and falling out of favour.
And Waddock is enjoying trying to help him fire.
He said: ‘Barchy is a talented player, I know a lot about him and have seen him at his previous clubs.
‘I tried to sign him once before when I was at Wycombe, he knows I like him!
‘When I came in I had one or two conversations with him and he has come back into the team, after a period out with injury and trying to get his fitness levels up.
‘He’s a nice lad and a talented individual, I have a lot of time for him. If he can now just be consistent with his work rate and performances he is going to be a threat for us going forward.
‘Barchy’s got pace, is a threat, he scores goals, he can bring teams up the pitch with his pace so if you have somebody like that in your side on the left-hand side and someone else on the right-hand side (Jed Wallace) who also has energy and pace, they are dangerous players.
‘He has got to recapture that form and as staff we have been helping him achieve that. You can see the talent is still there, we just have to get him to a level where he can perform and do it week in, week out.’
Now injury-free, Awford has recognised what Barcham has to offer.
Following just five starts and 18 appearances in total in 2014, the winger has become a regular feature of the Blues’ match-day squads of late.
Such was his impact in the weekend defeat to Southend, there was an adverse reaction from many fans when Awford substituted him for tactical reasons.
Signs then that Barcham is on his way back.
Waddock added: ‘If you are in and out of the team with injuries you are never going to get that performance right.
‘Your fitness levels are not going to be right because all of a sudden you have one injury and then another and haven’t got that consistency in your game.
‘Confidence will be an issue as well because if you are going in and out of the team you can never have a regular place so we have just got to make sure we get the best out of him.
‘We have been working with all the lads in training. Sometimes it is just a chat, a quiet word in his ear or a one-to-one to get the best out of them.’