Maybe the last time Cristiano Ronaldo failed to get his own way over a transfer was in the summer of 2008 and on that occasion it didn't work out too badly for Manchester United.
Ronaldo was desperate to join Real Madrid after five seasons at Old Trafford and the transfer saga was a toxic one. United reported Real to FIFA and Ronaldo himself said he was "a slave" for being forced to stay at United, a club where he had four years left on a generous contract.
Ultimately, United failed to cave in during the summer of 2008 and kept Ronaldo. Sir Alex Ferguson refused to give in to Real Madrid and not only managed to keep Ronaldo, but also coax another superb season out of him.
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There was an acceptance Ronaldo would be gone the following year and the goals did dry up a little, scoring 26 times in 53 games in 2008/09, but he won the Ballon d'Or that season and United won the title and reached the Champions League final, before Ronaldo sealed that move to Madrid.
United's hardline negotiations worked well 14 years ago, keeping a world-class player for another season and still pocketing a substantial fee. Ever since then Ronaldo has generally called the tune on his career and to assess how times have changed, it's worth recalling a Pep Guardiola quote from last summer, when it looked like Manchester City would sign him rather than United.
"In my personal view, there are few players, Cristiano included, Messi of course, they decide where they are going to play," said Guardiola. "Cristiano will decide where he wants to play. Not Man City, not myself."
Now Ronaldo has decided he doesn't want to play at Old Trafford and if it's surprised anyone at United than they've been guilty of naivety. A player as relentlessly ambitious as Ronaldo was never going to accept spending one of his final seasons at the elite level by gracing the Europa League.
United insist Ronaldo is not for sale and has a year remaining on his contract, but right now the chances of him seeing that year through must be receding. Getting another year out of him now is a lot more difficult than it was in 2008.
Even then, when United were at the peak of their powers and Ronaldo still had a long career in front of him, Ferguson had to fight to keep him. Now, United have lost the power they once had.
It is the club's fault they are in this position after a series of poor decisions last season. When you sign a player like Ronaldo, it comes with an unwritten rule that you have to provide conditions for success, and they've not done that at Old Trafford.
The 37-year-old can also hear the clock ticking louder than ever. Who knows how long he will go on, but his time at the very top is clearly limited and if there's a chance of getting back into the Champions League then he will fight hard to take it.
United can certainly be aggrieved at the timing of it, although that is unlikely to be coincidental. Ronaldo may have had enough of the club's slow start to the transfer window, or agent Jorge Mendes might have waited until he knew there was a Champions League market for his star client.
It's put the club on the backfoot at the very start of the Erik ten Hag era and all the positivity that the appointment of the 52-year-old should have generated could be swamped by a long-running transfer saga, but we stand on that precipice at the moment.
Ronaldo has been absent from Carrington for successive days at the start of pre-season due to "family reasons" and United are in the dark over when he will return, or if he will be on the flight to Bangkok for the start of the pre-season tour on Friday.
It's an unfortunate distraction for the club at the wrong time. They are close to completing the deals for Tyrell Malacia and Christian Eriksen, but both could be overshadowed by Ronaldo's future.
Fourteen years ago United managed to wield some power in a similar saga, but this time it feels like that is all in the hands of the player himself. If Ronaldo really wants to leave, then stopping him is going to be difficult.
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