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!
13. Theodoros Zagorakis (2004/2014)
Pompey Pedro says: He’s good but he’s no Giannis Skopeletis. Picture: Alex Livesey/Getty Images Photo: Alex Livesey
14. Andriy Shevchenko (2005/2015)
Pompey Pedro says: Coming out of retirement to show Kal Naismith how to play number 9. Picture: Laurence Griffiths/Getty Images Photo: Laurence Griffiths
15. Zinedine Zidane (2006/2016)
Pompey Pedro says: Pining for the sights and sounds of Old Portsmouth, Zizou returns for a second stint, forming an unstoppable attacking trident with Gary Roberts and Curtis Main. Picture: Michael Steele/Getty Images Photo: Michael Steele
16. Andrea Pirlo (2007/2017)
Pompey Pedro says: The majestic Italian Maestro Pirlo turns down the bright lights of New York FC in the MLS for the opportunity to play alongside his English equivalent and spiritual successor, Benjamin Close. Picture: Newpress/Getty Images Photo: New Press