For around 48 hours it seemed that the Portugal star was on his way to the Etihad Stadium, so how did he instead end up at Manchester United?
Too old, too expensive and a bad fit.
And yet. somehow, Cristiano Ronaldo very nearly ended up as a Manchester City player.
In the space of a crazy 48 hours, the Portugal international first appeared to be on the verge of a move to the Etihad Stadium, only for neighbours Manchester United to nip in on Friday and instead bring Ronaldo back to Old Trafford.
But how close did Pep Guardiola really come to adding the five-time Ballon d'Or winner to his squad?
Sources have told Goal that Ronaldo had actually first been offered to City earlier in the window, with super-agent Jorge Mendes having spent the summer trying to find a club for his client after the 36-year-old made it clear that he wanted out of Juventus.
Mendes is understood to have approached some of Europe’s biggest clubs - including both Manchester sides - in a bid to find a suitor who could offer Ronaldo both the ambition and salary he required, but no teams were forthcoming with offers.
City, for their part, were clearly in the market for a forward following the departure of club-record goalscorer Sergio Aguero on a free transfer to Barcelona.
But, as has been clear all summer, it was Tottenham striker Harry Kane who was identified as the top target early in the window, with the England international also keen on moving to the Premier League champions.
However, extricating Kane from Spurs proved difficult as the transfer saga rumbled on through the summer. Tottenham chairman Daniel Levy insisted the striker was not for sale, and six days before the transfer deadline, Kane admitted defeat and committed his future to the north London outfit.
With Kane off the table, Mendes leapt back into action. The Portuguese has good relations with City, with a stable of his clients including Ruben Dias, Ederson, Joao Cancelo and Bernardo Silva all at the club, and he was keen to add Ronaldo to that group.
This time, City were more open to negotiating with Ronaldo, particularly after it became clear that he was keen on a move to the club despite having said in the past that he would never play for United's cross-town rivals.
Despite some reports that a deal was close to being agreed, the consistent noises coming from the Etihad throughout the whirlwind saga were that an agreement was "unlikely".
Juventus wanted £24 million ($34m) for the forward to avoid suffering a capital loss, while City did not want to pay a fee to sign him. United eventually paid an initial £13m ($18m), with further add-ons valued at up to £7m ($9m), to add him to their forward line.
While Ronaldo's return to Old Trafford is a romantic one, any agreement between City and Ronaldo would merely have been a marriage of convenience, and there were understood to be concerns on both sides.
The ex-Real Madrid star turns 37 in February and therefore could never be considered a long-term signing, while there were issues over how he would fit into the squad too.
Off the field, there are few big egos inside the City dressing room, with leaders such as Fernandinho and Dias keen to maintain a balance through the group
On the field, Guardiola's success at City has been built around a team ethic, with hard pressing starting with his forwards and running throughout his side.
That is partly why he was able to lead City to a Premier League title and to the final of the Champions League last season despite Aguero being missing for much of it.
“Off the ball, they have to run like it was the last minute of their life,” the City boss said in his press conference ahead of Saturday's victory over Arsenal. “I don’t like it when I see a player who doesn’t run. I don’t like it at all.
“They have to convince me why the other team-mates can run and this guy cannot run. If he convinces me of that and convinces his mates, maybe. If he doesn’t run for the other ones, I don’t understand the theory.”
"The guy" that Guardiola spoke of was a purely hypothetical player, although some believed it was a pointed reference towards Ronaldo.
His answers had been delivered shortly before 2pm on Friday afternoon, when publicly Ronaldo's next move was still unknown, though it was becoming clearer that a move to United was on the cards. Within half an hour, City confirmed they would not be signing him.
As well as City's concerns, sources have told Goal that Ronaldo was worried about whether he was really wanted by Guardiola after he turned down the chance to sign him earlier in the window
And when United were spooked into a making their move by the thought of a club legend wearing the sky blue shirt of their city rivals, Ronaldo's mind was made up, helped by interventions from Sir Alex Ferguson, Rio Ferdinand, Patrice Evra and Bruno Fernandes.
City, then, remain without a striker, and with fewer than 48 hours until the window shuts, sources say that a last-minute deal is unlikely.
With at least 30 goals in 11 of his last 12 seasons, there was every reason to believe that Ronaldo would have had an impact at the Etihad. That would have been true off the pitch too, with his superstar status as one of the two best footballers of a generation likely to generate interest in City from outside of Manchester.
But there were also reasons why he was never a priority, and that is ultimately why what would have been one of the most surprising transfers of all time never happened.
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