Ed Woodward will leave Manchester United with more regrets than the number of different managers he has hired and fired.
But his biggest one of all from his controversial, rollercoaster ride as executive vice chairman will be over the boss that somehow slipped through his fingers.
Jurgen Klopp is the man Woodward believes could have made the best fist of filling the boots of Sir Alex Ferguson when he retired in 2013.
Instead, that task fell to David Moyes, who lasted just 10 months before being sacked.
Woodward also appointed Louis van Gaal, Jose Mourinho, Ole Gunnar Solskjaer and, most recently, Ralf Rangnick on an interim basis, but knows none of them have been that elite one the club needed – and still does – to sustain the remarkable success Fergie engineered.
The likes of Klopp, Pep Guardiola, Thomas Tuchel and Mauricio Pochettino have all been available at some stage, but none of them ever arrived at Old Trafford.
He flew to Germany to speak to Klopp in 2014 after dismissing Moyes, but was left shattered when he chose to join bitter rivals Liverpool instead.
The rest, as they say, is history, and it's one that will see Woodward's reign forever stained with the fact United haven't come close to winning the Premier League title in almost a decade, despite spending almost £1billion on high-profile and often knee-jerk signings.
Superstars have come and gone, but United remain in the same place as when Woodward took charge. Seventh in the table and 22 points adrift of the team at the top of it.
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To make matters worse, Woodward was forced to fall on his own sword last April in the wake of United's role in the scandalous European Super League proposal that rocked the game to its core.
He resigned once he decided he could no longer back United's involvement in it, just 24 hours before the sickening plot collapsed altogether.
This remains one of his other regrets, along with the fact he discovered Fergie was stepping down as manager just days after he took the reigns from David Gill.
The pair met for lunch at Mayfair restaurant 'Scott's' and after ordering an expensive bottle of red wine, Fergie dropped the bombshell that left Woodward wondering if his new role at United was as appealing as it looked.
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How could he do the job if he couldn't learn from a man he still considers to be a genius?
Woodward will hold his hands up to making some big mistakes, but will also argue he leaves the club in a better place than the one he found it.
United have a more modern recruitment and scouting process, state of the art training complex, sponsors tripping off the tongue, a monstrous commercial revenue and less antiquated stadium.
But all that matters to supporters is results – and United continue to wade through treacle on the pitch.
This resulted in him becoming a punchbag for all those who deemed him a floundering failure. His house was attacked, forcing him to sell up and move back to London, one group of fans on a Europa League trip to Kazakhstan plotted to spike his drink with tabasco sauce, while his wife Isabelle even received rape and death threats online.
When things don't go well, someone has to take the blame and while Woodward accepts this, he also knows some of it did more than cross the line.
He will now step aside to let Richard Arnold take charge and the new chief executive officer has quite a job on his hands.
There have been ups, downs and a lot of in-betweens, but ultimately Woodward will depart without the one thing he craved – a league title.
And he'll never be allowed to forget that for this, most people will always hold him responsible.
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