I'll start. Obviously, I'll cover the Arsenal but feel free to add any I miss.
Take a look at this fucking list (some are mentioned in the article):
1- Diego Maradona (1978) - in his prime!
2- Johann Cruyff (1976)
3- Christiano Ronaldo (2003)
4- Zlatan Ibrahimovic (2002) - You need to read Zlatan's quotes about this (they're just too funny).
5- Yaya Toure (2003)
6- Didier Drogba (2002)
7- Petr Cech (2002)
I cannot wrap my head around some of these. Let's be clear these weren't based on speculation or loose associations. These were deals that were inches from being signed. Some fell through because of monetary reasons, some because of personality issues, while others were simply errors of judgement. In any case, no one can say for sure that that these players would have been just as good had they signed. Still, that doesn't mean we can't imagine "what could've been".
PS: IF YOU'RE GOING TO CHIP IN, MAKE SURE THEY WERE DEFINITELY CLOSE TO SIGNING. I DON'T A LIST OF WILD SPECULATIONS THAT HAD NO GROUNDING IN REALITY.
I came across a fantastic article, surprisingly written by the folks over at ESPN on significant transfer fees that could have been. I recommend reading it Source:
http://soccernet.espn.go.com/columns/story/\_/id/1125402/first-xi:-the-deals-that-could-have-been?cc=5901
But it made me think that this would be a great topic of discussion. There are many more than the ones listed in the article and I thought everyone could maybe research a few from whatever team they follow or have an interest in.