Not only must he make his mind up on the 10 senior players whose contracts expire at the end of the season, he’ll also have to make the call whether the Blues make any of their loan signings this season permanent ones.
So what are the chances of that happening? Is there scope of any of the five who currently call Fratton Park home staying?
Here, we take a look, rating each player’s chance of remaining at Fratton Park out of 10.
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From left: Di'Shon Bernard, Matt Macey, Owen Dale, Dane Scarlett and Joe Pigott Photo: National World
2. Matt Macey - 8/10
The 28-year-old keeper has made an instant impression since arriving at Fratton Park in the January. So much so that John Mousinho has stated already that he'd be interested in making his loan move from Luton permanent. You'll find it hard to find anyone who would challenge that decision, with Macey keeping six clean sheets in his 12 games to date. Yet, nothing is ever simple. A fee would need to be agreed with Luton, with the former Hibs man having a year left on his Kenilworth Road contract. The Premier League-chasing Hatters would also have to be willing to part company with their summer signing. Meanwhile, there's also the player to consider. Does a keeper with Championship ambitions want to remain in League One? Macey has talked about his Luton loyalty but just as crucial, will he get the game time he craves if he returned? That, plus the Blues' desire to keep him, might tempt him to remain at Fratton Park. Photo: Jason Brown
3. Di'Shon Bernard - 5/10
The 22-year-old defender has made just four appearances since arriving from Manchester United in January. A player who can operate at both centre-back and right-back has seen his game time limited by Joe Rafferty's impressive return following injury - plus John Mousinho's apparent preference to keep faith with what is now a settled back four. No doubt, there's something about Bernard that prompted the Blues to sign him on loan. Meanwhile, he fits the profile of player that Pompey are keen to recruit going forward. But will their first-hand experience of the player prompt them to push for a permanent move? Possibly, although a contract at Old Trafford until 2026 might put the Blues off, with a sizeable transfer fee likely. How much game time Bernard gets between now and the end of the season will also be a key indicator. Photo: Graham Hunt
4. Dane Scarlett- 0/10
There's no denying that the Spurs youngster has a big future ahead of him - despite his recent struggles in a Pompey shirt. After such an impressive start to his Fratton Park career, the 18-year-old has struggled to reach those heights on a consistent basis since. That's not his fault, though, with the Blues representing his first proper taste of senior football. Meanwhile, the poor team form that led to Danny Cowley's sacking wouldn't have helped either. Regardless of what's happened here this season, however, Scarlett will return to Spurs as a better player and with much-needed experience behind him. Would Pompey love Scarlett on their books permanently? Of course, they would. Is that realistic - of course not. Photo: Jason Brown