Jose Mourinho, who was sacked by Tottenham on Monday, has been fired before winning a trophy for the first time as a manager, in the latest setback to a career veering increasingly off course.
The Portuguese coach, a serial winner across Europe, arrived at Spurs 18 months ago with a point to prove after his reputation was tarnished by his more than two-year spell in charge of Manchester United.
Despite a highly acrimonious reign at Old Trafford, the self-declared "Special One" still claimed three trophies, including the 2017 Europa League, although another was the Community Shield.
Mourinho's failed Hotspur project is evidence his coaching methods are not as effective as they once were as he leaves a club without a trophy for the first time since the early days of his coaching career in Portugal.
Despite a wealth of attacking talent at both Spurs and United, Mourinho's negative tactics drew much criticism.
Former Spurs midfielder Jamie Redknapp said in December Mourinho was "asking for trouble" with such a reserved approach, while ex-striker Darren Bent labelled Mourinho's tactics "outdated".
While Juergen Klopp's high intensity approach has revolutionised the way Liverpool play, and Pep Guardiola's ever-evolving Johan Cruyff-inspired system has steered Manchester City to much success, Mourinho's style has remained unmoved.
Chairman Daniel Levy wanted a blockbuster name when he went for Mourinho, with an Amazon documentary to sell, but on the morning after Spurs joined the prospective 12-team European Super League, Mourinho was surplus to requirements.
There is much uncertainty in the game after the announcement of the much-maligned Super League, with it unclear what the footballing landscape will look like across the continent.
Mourinho's future looks equally up in the air.