Peter Lawwell began the season with dreams of helping boyhood club Celtic extend their dominance of the Scottish Premiership to a remarkable 10th successive year.
But, just as the Hoops are almost certain to relinquish their stranglehold on the title to bitter rivals Rangers, he will finish it with his personal grip on power at an end.
The 61-year-old is set to retire as chief executive in the summer after 17 hugely successful years at Parkhead.
Celtic have won a staggering 29 trophies during his lengthy tenure, in addition to enjoying three trips to the last 16 of the Champions League.
Yet a failure to even threaten increasing that haul to 30 during a tumultuous campaign on and off the field, combined with long-standing resentment over his failure to maximise Celtic's dominance over Rangers during the years when the Ibrox outfit were forced to rebuild following their financial collapse, means news of his impending departure has sparked little sorrow among sections of a frustrated fanbase feeling increasingly disconnected.
Dominic McKay, Scottish Rugby's chief operating officer, has already been appointed as Lawwell's replacement in what will be a new era for the Glasgow giants.
A passionate lifelong Hoops supporter, Lawwell re-joined the club in October 2003 – he had previously had a short-stint as the financial controller in the early 1990s – from his position as commercial director with Clydeport plc, having also formerly held senior roles with chemical company ICI, healthcare firm Hoffmann-La-Roche, and Scottish Coal.
Widely respected among his peers, Lawwell was a powerhouse at boardroom level, with some feeling the control he exerted extended to the whole of Scottish football.
Asked in January 2017 who was running the game north of the border, former St Mirren chairman Stewart Gilmour offered an unequivocal response.
"I don't think you need to ask me that. Are you trying to tell me that Peter's not pulling the strings? Peter Lawwell?"
Meanwhile, his fearsome reputation at the negotiating table was epitomised by comments made by Lyon owner Jean-Michel Aulas the following year.
"He is basically like a bulldog who negotiates after yapping. He's a good friend, a great guy and very difficult in negotiations," said Frenchman Aulas.
For all of his business acumen and the team's successes, Lawwell's hefty salary was often a bone of contention.
At the club's 2019 AGM, a supporter jokingly asked how many goals the boardroom member had scored the previous season to justify total earnings exceeding £3.5million.
Club chairman Ian Bankier and manager Neil Lennon each issued staunch defences of the eye-watering pay cheque, which included bonuses.
Bankier admitted "it looks bad" but that his colleague was "worth every penny", with Lennon adding: "Peter is the best, and sometimes you have to pay for the best."
Many supporters clearly did not agree and the recent rocky period has only increased the scrutiny on his role.
Concerned about what they claimed was the club's downsizing following the departure of all-conquering boss Brendan Rodgers, fans unfurled a flag back in August 2019 warning Lawwell and majority shareholder Dermot Desmond not to "fall asleep at the wheel".
The warning has not been heeded and this season – when Celtic were supposed to be fulfilling their 10-in-a-row destiny – they have crashed, leaving Rangers to speed off into the distance.
Spinning out of the Champions League yet again and seeing their four year grip on Scotland's domestic silverware ended with a shock Betfred Cup exit to Ross County have been compounded by Lennon's league struggles, with his team now 23 points adrift of Steven Gerrard's rampant Ibrox side.
That County defeat sparked angry protests outside Parkhead's front door but Lawwell and Lennon clung onto their posts with the backing of Desmond, the club's all-powerful benefactor.
But the negative headlines have rumbled on. There was also a huge furore over an ill-judged decision to take the squad to Dubai for a mid-season training camp.
Lawwell admitted the trip to the United Arab Emirates had been "a mistake" – but only after defender Christopher Jullien's positive coronavirus test on return forced 13 of his team-mates into isolation, along with manager Lennon and his assistant John Kennedy.
Clashes with the fans are not new. He has repeatedly butted heads with ultras group the Green Brigade, claiming in November 2019 that their behaviour at games had cost Celtic more than €500,000 (£442,312) in UEFA fines.
The supporter group responded to the surprise news of the chief executive's imminent exit – released just after 7am on Friday – by tweeting: 'One down, more to go'.
Despite failing to satisfy everyone, Lawwell leaves a trophy-laden legacy, which includes 13 league titles and an unprecedented four successive domestic trebles.
His retirement statement expressed disappointment at how the final year has played out and pledged to work on a "seamless transition" with successor McKay as the club prepare for the unfamiliar position of attempting to reclaim, rather than retain, the title.
He also made a deliberate point of highlighting the vital role of the club's vast fanbase, with whom, at times, he endured such a testing relationship.
"Celtic will always be the biggest and the best club in Scotland and our supporters will always be everything to our success," said Lawwell.
"We need our fans with us to achieve that success."