Now Blues supporter @PompeyPedro (Twitter name) has been brave enough to do just that.
Just who could Pompey have signed if they had followed up their move for former Real Madrid and Barcelona superstar Robert Prosinecki using a similar tactic?
Yes, the chain-smoking Croat arrived at Fratton Park in 2001 – 10 years after he finished fifth in the 1991 Ballon D’Or vote.
Crazy, we know, bearing in mind Pompey finished 20th in the second tier just the season before.
Yet imagine if the Blues had continued that tradition from then until today? What could have been?
Well, as we’ve said, @PompeyPedro has taken a light-hearted look to see just who could have arrived at Fratton Park and followed in Prosinecki’s footsteps in calling the south coast home.
And it’s proven a huge success on Twitter, with thousands of fans loving his work and his wisecracking comments on each player.
Andrea Pirlo linking up with Ben Close? Roberto Carlos serving as Matty Taylor’s back-up? Zinedine Zidane laying them on a plate for Curtis Main to tuck home?
Who wouldn’t get excited by those prospects?
Here’s what @PompeyPedro discovered!

9. Alessandro Nesta (2000/2010)
Pompey Pedro says: He loved the atmosphere so much in the Milan game in 2008 that he’s come back for a swansong. The Nesta/Rocha back line is unrivalled. Picture: DAMIEN MEYER/AFP via Getty Images. Photo: DAMIEN MEYER

10. Francesco Totti (2001/2011)
Pompey Pedro says: L'Ottavo Re di Roma (The 8th King of Rome). Takes a year sabbatical from the Holy City for an arguably more culturally enriching experience on the south coast of England. Picture: Paolo Bruno/Getty Images Photo: Paolo Bruno

11. Michael Ballack (2002/2012)
Pompey Pedro says: Michael Ballack comes to town teach Michael Brown what a midfield destroyer really looks like. Picture: Stuart Franklin/Getty Images) Photo: Stuart Franklin

12. Zinedine Zidane (2003/2013)
Pompey Pedro says: Fine. We’ll take him! Picture: Stuart Franklin/Getty Images) Photo: Stuart Franklin

