And now, with Mourinho not attached to a club and Chelsea without a manager for the year ahead, it seems the 50-year-old could be coming to London.
Real Madrid president Florentino Perez made the stunning announcement about Mourinho's departure this morning in front of a packed news conference (per BBC).
We've decided to bring our relationship to an end. Nobody's been sacked, it's a mutual agreement. The club and manager agree the timing is right to bring our relationship to an end. On behalf of the board of directors, I would like to thank Jose Mourinho for all his hard work. The team has improved in his three years and we wish him all the best.
Assuming Mourinho does end up signing with Chelsea, it will no doubt be a move well-received by the Blues' faithful. They've endured a tumultuous 12-month period that saw them go from the lowest of lows in the Champions League to a thrilling high in the Europa League Final. What's more, they've endured a managerial circus that has done nothing but cripple the support and belief of the club.
Now, it seems, having Mourinho back would fix some of that.
"The Special One" would return to the club that he last managed in September 2007 as a legend, having won titles in both Spain and Italy since his departure.
However, as great and illustrious as his trophy cabinet may be having chalked up much success over the years, the reality is that Mourinho is by no means the Messiah for Chelsea.
In fact, he would come to the West London club under a mountain of expectation and pressure that, if he fails to live up to, could well see him fall under the wrathful fist of owner Roman Abramovich once more.
For Mourinho would be somewhat expected to have success at Chelsea.
After all, he is the larger-than-life man himself—The Special One, right?
Well, yes, but it must be noted that six years is a very long time to be away from a club. The Blues have had many highs and lows in both England and Europe since then, and whilst Mourinho no doubt boasts the resume to handle whatever the Blues' needs are, six years is still a very long time.
BBC5's Ian McGarry wrote about Mourinho's potential return:
I think he's [Mourinho] romanticized the relationship with the [British] media a little. It wasn't as cushty as he's made out in press conferences over the past few months, when he said he is loved by fans and the media. We do Jose, but for a reason. It doesn't mean you love us all of the time. We've had our fall-outs...
He also went on to state that he would return to a "very different Chelsea team" and a "very different landscape" since he last was in charge, and it's true.
The legends like Didier Drogba have been replaced with the up-and-coming stars of Juan Mata and Eden Hazard. Yet more importantly, Chelsea have slipped from being at the top of England, to being back behind Manchester United once again, and they're now behind Manchester City also.
That's what Mourinho would come back to, and if his time at Madrid is anything to go by, then he would certainly be under a lot of pressure to instantly deliver.
And when it comes to Chelsea, that means trophies.
Mourinho's trophy-resume is impressive, with a long list of titles from around the world. However, it must be noted that since leaving Inter Milan for Madrid, Mourinho has secured just two titles—the Spanish La Liga title and the Copa del Rey.
As far as domestic success goes, Mourinho has delivered nothing but semifinal heartbreak for Los Blancos fans around the world.
That might sound harsh, but we're talking on Chelsea's terms here.
If Abramovich is happy to part ways with the man that won the European competition—Di Matteo—then Mourinho must also be held up to the same standards.
He might be The Special One (or even "The Only One"), but if he cannot deliver for Chelsea what is expected of him, then he will be on the outer once again.
That's the environment that Mourinho would be coming into.
He would be under pressure from the opening whistle next season, and his successes or failures at Chelsea would therefore stand as the defining moment in his legacy.
If he were to lead the West London club back to European success and Premier League domination, then it would be a success. If he were to lead the Blues back to the Promised Land, per se, of being one of the world's best once again, he will have fulfilled his job description in its entirety and Mourinho's legacy as The Special One will go down in Chelsea folklore forever.
But if he were to have another season like he just did at Madrid, or like the Blues just had in England, that legacy and reputation would certainly be put on hold.
And that's the problem with having great expectations for the future.
After all, the reality is that in 2013 Benitez won more titles than Mourinho. Chelsea had the same number of trophies in six months of Di Matteo that Mourinho did in three years at Real Madrid—and that was with a squad boasting Cristiano Ronaldo, Mesut Ozil and so many other superstar-esque players.
Mourinho arrived at the Bernabeu a legend, and left it a mess.
His legacy as that of The Special One is definitely on the line this summer, and if he chooses Chelsea, he'll have a very tough time justifying that claim.
That's not to say that he won't; just to say that it will be very difficult.
Even for The Special One.
Hit me up on Twitter for more sports goodness: Follow @dantalintyre
Like the new article format? Send us feedback!