Manchester United executive vice-chairman Ed Woodward failed in his high-stakes gamble to join a European Super League and the clock is now ticking on his tenure at Old Trafford.
When he was a banker with JP Morgan - the US investment giant that was set to finance the ESL - Woodward once complained about colleagues moaning they were losing their jobs and reminded them that "part of the high rewards were the high risk".
Although he was already due to step down, the timing of the announcement on Tuesday appeared no coincidence on a breathless evening when United and their Premier League rivals withdrew from the Super League after fierce opposition from supporters.
Clubs in Spain and Italy followed suit on Wednesday as the project fell apart.
Many United fans would say it was not a moment too soon for a man they never warmed to and who people that know him term charming but ruthless.
Just as manager David Moyes had a hard act to follow in Alex Ferguson, so Woodward, who is stepping down at the end of 2021, had a tall task to emulate his boardroom predecessor, David Gill.
Woodward has been executive vice-chairman at Old Trafford since 2012. He took over the responsibilities of departing chief executive Gill the following year.
However, while Gill managed to move from a successful career outside football to being a perfect partner for Ferguson, Woodward never quite managed the leap.
Part of that was due to a lack of success since Ferguson stepped down -- United have not won the Premier League since 2013.
Woodward, 49, had appeared to retain the backing of United's US owners, the Glazer family, despite having no league title or Champions League trophy to show for investment of nearly 1 billion ($1.4 billion).
In a defiant statement to accompany the announcement of his departure, Woodward insisted he believed the money was well invested.
"We have invested more than 1 billion in the squad during my time here," he said.
"I am particularly delighted with the progress the players have made under the astute leadership of Ole Gunnar Solskjaer and his coaching team in the last two years."
Instead of Woodward leaving it was the managers who came and went through the revolving door - Moyes only lasted 10 months.
Dutch coach Louis van Gaal - "the perfect choice" as Woodward termed him - lasted two years but much of the wastage on transfers including Daley Blind and Matteo Darmian.
"I blame Ed Woodward, my CEO at Manchester United, much more than (Jose) Mourinho (his successor)," Van Gaal told the Een-tweetje met Yves podcast, referring to his brutal sacking in 2016.
"In my view, Woodward is the evil genius."
Woodward basked in the initial glory of Jose Mourinho's reign -- a Europa League and a League Cup trophy before, as it often does with the Portuguese coach, it went sour and he was sacked in 2018.
Through it all though Woodward stayed put, enjoying the confidence of the Glazers, whose ties with him go back a long way.
It was Woodward who, when working for JP Morgan, advised the Glazers on their purchase of United in 2005.
They looked to the physics graduate as a sharp mind and reassuring face to have around and brought him on board.
"His contribution to the club has been massive, and he will always be welcome at Old Trafford as a part of the Manchester United family," said United co-chairman Joel Glazer.
He certainly earned the Glazers' loyalty as he bore the brunt of the fans' ire at the family who have largely stayed in the United States.
Balaclava-clad fans attacked his home last year, launching flares, and some sang "Woodward's going to die" when United lost to Burnley at Old Trafford in January 2020.
Woodward will brush off the comment of UEFA president Aleksander Ceferin, who called him "a snake" over the Super League fiasco, but it could take him a while to recover from the shambles it has become.