Manchester United manager Alex Ferguson, who has reduced hardened internationals to quivering wrecks and sold the biggest names, is discovering the limits of his powers after failing to persuade Wayne Rooney to stay.
Rooney may yet change his mind, but the prospect of the England striker following Cristiano Ronaldo and Carlos Tevez out of Old Trafford leaves Ferguson to contemplate another major rebuilding job as he approaches a quarter-century in charge.
With the generation of players that helped United reach its exalted state, the likes of Ryan Giggs and Paul Scholes, edging toward retirement, the 68-year-old Scot has a lot to consider and he could be forgiven for sounding exasperated as he shocked reporters with the Rooney news.
In fact, he seemed genuinely stunned that anyone, let alone an English player nearing the peak of his ability like Rooney, would want to walk away from Old Trafford.
English newspapers have highlighted how the likes of David Beckham, Roy Keane, Ruud van Nistelrooy, Jaap Stam and Paul Ince, despite their high-profile presence, were shown the door after getting on the wrong side of the manager.
However, this case is very different.
Ferguson said on Tuesday he was originally informed of the Rooney decision by the club's chief executive David Gill and only then listening to the player tell him he "wanted away".
That left him annoyed professionally and hurt personally, and in his appearances in front of the media on Tuesday Ferguson almost sounded like a disappointed father forced to face up to the wrongdoings of an errant son.
"I couldn't believe it. I was dumbfounded," Ferguson told MUTV. "We've done everything we can for Wayne Rooney since the minute he's come to the club. We've always been there as a harbor for him.
"We've done nothing but help him in terms of his private life and other matters... the advice we've given him - I've even been prepared to give him financial advice, many times," Ferguson added.
Inevitably there will be questions about how long Ferguson, who announced a U-turn over a planned retirement back in 2002, will go on.
In front of a packed news conference, Ferguson was nothing like his sparky self as he read from a prepared statement, saying in March Rooney talked about staying at United for life and how he had no idea what had changed the striker's mind.
As a man who combined his early playing career with a job on the River Clyde shipyards, it seems Ferguson has never entirely come to terms with the mind-boggling financial rewards of the modern game and its effect on players.
Even in his early years at United, the club still farmed young players out to stay in the modest guest houses surrounding its Cliff training ground, where trusted adults kept a keen eye on their charges and ensured curfews were observed.
These days United's teenaged signings earn enough each year to buy those houses outright several times over.
"There is a disappointment a lot of the time when you have to deal with modern-day players," Ferguson said on Tuesday.
"It's not as easy as it was many, many years ago when you were negotiating a contract, because then the player had to depend on and trust the manager. And as a manager, you had more contact with the parents then as well.
"We are dealing with agents who live in the pockets of players... we live in a different world now and we have to deal with it in a different way. It's a pity, but it's there."
Of course, as he bemoaned the lack of loyalty among modern players, Ferguson overlooked the fact that Everton, which brought Rooney through its ranks before losing him to United as an 18-year-old, was similarly frustrated when the Old Trafford club came along waving its checkbook six years ago.
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