Could Pompey boss unearth another gem?
There was a certain shrewdness in Kenny Jackett's voice as he reflected on his previous Pompey encounters in his first press conference.
During his managerial career, the new Blues boss has had more good days than bad at Fratton Park.
In one particular game, Harry Kane scored the winner when on loan at Millwall.
Jackett grabbed the chance of moving to Pompey, despite a £3m budget that places them in the lower reaches of League One.
There are a few voids that need filling, too, particularly in between the sticks, on the left-hand side of defence and up top.
It would be no surprise to see Jackett plug those gaps with loan talents, a tactic he’s used to great success in the past.
Kane was just 18 when he moved to the Den for the second half of the 2011-12 season.
The future England international was highly touted at White Hart Lane, but he was joining a club who were facing relegation.
A risk you could say on Jackett’s behalf, bringing in a rough-edged junior – but fortune favoured the brave.
Kane bagged seven goals in 22 appearances and Millwall kept their Championship status comfortably and finished 16th.
‘Kenny Jackett persuaded me to join,’ Kane said.‘It was a big part of my development.
‘It really was a great learning curve for me, a fantastic experience.’
The 23-year-old is just the jewel in the crown of the players Jackett has drafted in on short-term deals.
Ryan Mason also moved to the Lions with Kane in 2012 and made five appearances. He played 16 times for Hull last term.
One year earlier on an emergency deal, Jackett sealed the services of Jason Puncheon from Southampton.
Millwall fans would have been gutted to see him leave the Den after just seven games as he netted five times.
But his replacement was like-for-like as Jackett swooped for Spurs’ Andros Townsend.
It was the future Crystal Palace winger’s fourth club of the season and there would have been doubts if he would ever reach his potential.
That changed under Jackett and Townsend revealed he settled down at Millwall.
‘I’ve been able to relax here and be confident from the off,’ he told the Daily Telegraph after his side’s 3-2 defeat of Leeds.
Adam Smith and Benik Afobe are both thriving on the south coast at Bournemouth.
The duo also spent time at the east London club and the latter was signed by the Blues manager at Wolves.
Liverpool’s Sheyi Ojo had a period at Molineux and has helped England under-20s reach the final of the World Cup.
After leaving Rotherham, Jackett took up a role with Spurs’ Academy.
Mauricio Pochettino is a boss who emphasises the importance of youth.
The former Espanyol No1 would not be afraid to send out his young protagonists if they need regular first-team football.
You can bet Jackett will already have a few in his mind.
And Pochettino won’t hesitate about picking up the phone and packing them off to P04 given Jackett’s record.