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!
5. Jurgen Klinsmann (1996/2006)
Pompey Pedro says: Not sure he’d have had the legs at this point. Picture: BERND WEISSBROD/AFP via Getty Images Photo: BERND WEISSBROD
6. Roberto Carlos (1997/2007)
Pompey Pedro says: Bobby C. Does he do what Matty Taylor does? For me? No. Bench. Would’ve been useful in the great escape run in though. Picture: ANTONIO SCORZA/AFP via Getty Images Photo: ANTONIO SCORZA
7. Rivaldo (1998/2008)
Pompey Pedro says: Arrives after a Harry Redknapp spells Reo-Coker wrong on the paperwork. Slots beautifully into the all time great 2008 Pompey squad. You’d have to imagine a Lassana Diarra/Rivaldo pivot would’ve been filthy. Picture: Gary M. Prior/Getty Images Photo: Gary M. Prior
8. Luis Figo (1999/2009)
Pompey Pedro says: Could he have done it on a cold night away at Wigan? Probably. Picture: Mark Thompson/Allsport Photo: Mark Thompson