From a 41-year-old whipper-snapper just starting out at the top level of management, Jose Mourinho has come a long way and seen a lot of things in the 14 years since he joined Chelsea.
From England to Italy to Spain and back to England again, the Portuguese has taken charge of four different clubs since 2004, winning six league titles in that time.
None, it must be said, have come in the last six years, and time now seems to be taking its toll on the former housewives’ favourite.
From the man once famously labelled ‘good-looking’ by Sir Alex Ferguson, Mourinho seems to have become a shadow of his former self and no longer seems capable of taking Manchester United to the very top of the game.
It all started so well for Mourinho. When he arrived at Stamford Bridge in 2004, there was just a hint of grey at the side of his head, the majority still a jet black.
George Clooney was his lookalike, the silver fox, but now he is grey and becoming more and more disgruntled by the minute.
He looks tired, the Lowry Hotel doing nothing to rid him of the bags under his eyes. In actual fact, it would be wrong to put the blame solely on Manchester United.
A Mourinho with flecks of grey left Stamford Bridge for the first time back in 2007, with Inter Milan his next destination. At the San Siro he won two league titles, before moving on to the Bernabeu.
Perhaps the pressures of 81,000 fervent Madridistas week in, week out takes its toll on a man. Perhaps the regular meetings with the hierarchy demanding more trophies for this great club make life harder than it needs to be.
Whatever the reason, it is around the Madrid era that Mourinho’s flecks of grey turn more prominent. In fact, in 2013 as he returns to Stamford Bridge, he opts to shave his head, leaving just a grey buzz cut remaining.
It grows back, of course, but there is no back to black for Mourinho, instead just more and more shades of grey.
His second spell at Chelsea garners no new trophies and in 2016 he heads north to Old Trafford. A tough act to follow in Ferguson, a man he once consistently beat in his first spell at Chelsea.
But this is a different United, one devoid of recent success and a significantly harder task to manage. He doesn’t buy a house, instead opting to stay permanently in the Lowry Hotel.
Since moving to the North West, Mourinho has picked up three titles – An EFL Cup, the Community Shield and the Europa League – but they’re not the trophies the fans want. There’s no league titles or Champions Leagues, no hint of the glory days returning.
In recent weeks, things have reached fever pitch, and Mourinho seems angry all the time. Admittedly, there may be no way back for the jet-black hair of the early-to-mid 2000s, but some trophies may be needed to slow down the ageing process.