Daniel Levy is set to make a decision that will determine the future of Tottenham Hotspur and whether they build upon their first trophy in 17 years or simply step back into the crowd.
Ange Postecoglou is currently sitting on a beach in Greece awaiting the verdict from the chairman as to whether winning Spurs' first piece of European silverware in 41 years is enough for him to continue in the job. There wouldn't even be a conversation to be had at most clubs, but this is Tottenham where change is so frequent that staff might as well wear name badges to save the introductions.
The problem for Postecoglou is that for all the talk of Levy craving a trophy, it's not been as simple as that this season for the club. As the Australian decided to prioritise the Europa League when he realised his injury-ravaged side could neither do anything of note in the Premier League nor get relegated, so Spurs plummeted with weakened starting XIs and some woeful performances to 17th place and a record 22 defeats.
It was a terrible look and it meant a drop in prize money of £33.8million from the previous season's fifth place finish, if using the previous campaign's figures of £2.8million per position. That's a costly decision for Postecoglou to make and it will have been part of the reason why some within the club did not agree with him placing all of his eggs into the Europe basket.
In the end though Postecoglou's gamble paid off in both respects. Levy and Tottenham's trophy drought is finally over and the added bonus of Champions League qualification meant that not only did the Australian deliver every target asked of him, if not in the traditional manner, but plenty of money will flood in through Europe's elite competition, balancing out that lost Premier League prize money.
Yet whether that is enough will lie with Levy. The chairman is constantly tinkering with the north London club, always trying to make what he believes are updates and improvements, sometimes proactively, sometimes reactively.
It results in the biennial Tottenham wheel of change, where members of staff on the football side mostly last between 18 months and two years whether that be managers, coaches or technical directors.
The only stability at the club has come from the near quarter-century reign of Levy and his two trusted lieutenants, executive director Donna-Maria Cullen and operations and finance director Matthew Collecott. This summer that trio will be broken up after Cullen left the board on Saturday and will depart the club within the next couple of months.
For Collecott, who knows, there may yet be the potential of a change in role depending on what new CEO Vinai Venkatesham takes into his remit upon his arrival this week.
That leaves Levy with the sole decision to make over continuing the biennial clean sweep through the club with or without Postecoglou, who was the first Spurs head coach to last a full season in half a decade, in the broom's bristles.
One big problem for Levy is that the majority of Tottenham fans have swung firmly behind Postecoglou after he delivered them one of their most memorable nights in decades.
A few still point to the woeful league season, which cannot be ignored even if history likely will, but the numbers are with the Australian, as evidenced not only by the reaction to him from the estimated 220,000 supporters at the parade and then those at the final game of the season but also in various social media polls that show the huge majority believe Postecoglou has earned the right to go into the third season he promised would be even more fruitful.
The other issue Levy faces is who comes in next. When he sacked Mauricio Pochettino, he had serial winner Jose Mourinho to come in and dry the fans' tears. That brutal decision, while heart-breaking for many after the effort the Argentine had put in, was somewhat explainable when you looked at Mourinho's track record. There is a certain irony of course that Levy then sacked the Portuguese just days before he had a chance to finally win a trophy.
However, 2025 presents a very different managerial landscape. Thomas Frank and Marco Silva, for instance, are very good coaches but if Postecoglou is sacked after finally giving the fans something they've only dreamed of for either of the managers who finished 10th and 11th in the Premier League, the reaction is going to be huge from the fanbase and Postecoglou's name is likely to be awkwardly sung next season the moment something goes wrong.
To replace Postecoglou would create a huge 'what if' moment around the Australian going forward as well as no little mocking for Tottenham being utterly 'Spursy' after finally appearing to kill that tag.
Frank has been installed as the favourite among many bookmakers but Postecoglou may well point out that he has come out on top in three of their four meetings in the past two seasons and the other was a draw. For all of the Dane's clear tactical acumen and the Australian's perceived lack of it, it's been one way traffic.
Frank and Silva would both be a safe pair of hands in the Premier League, although Everton and Hull fans might disagree on the latter. They are both managers used to getting smaller teams into midtable positions without the burden of the expectations at Tottenham or even European football.
That in itself is another irony. Some of the doubts around Postecoglou linger on whether his style of football is sustainable across four different competitions. Yet Silva has no experience of managing a team in continental competition at all while Frank's experience extends only to a handful of ultimately unsuccessful Europa League qualifying games with Brondby 10 years ago.
That's not to say that either won't be able to succeed at Tottenham. They are both clever, high quality coaches and Frank in particular will be good value for the media. It's simply saying it's as much of a gamble as some might see keeping Postecoglou is. It's also a costly one for the Australian would need to be paid off for the remainder of his contract as well as his coaching staff and then compensation paid for the new man. Postecoglou could also reasonably argue any dismissal by pointing to what he achieved in the end.
On top of that, the squad rebuild would need to start again to suit a new manager's needs. It's going back to square one and overall it's a remarkable amount of money to pay out to make major changes after finally achieving success. For all of Levy's famed business acumen, it doesn't particularly add up as a smart decision or send a great signal to any prospective managers in the future about what they will be judged on in the role.
Postecoglou wants to remain at Tottenham and believes he's got so much more to achieve with this group of players, added to with a bit of experience, and that they will build on the platform of the trophy win. It important not to underestimate how strongly the dressing room is behind the 59-year-old as well.
It's not that Postecoglou will be worried either about life after Spurs. He is a European champion and will have job offers galore. He need only look at the most recent group of managers in Antonio Conte, Nuno Espirito Santo, Pochettino and Mourinho to see that there is life and silverware available immediately after leaving Tottenham.
But Postecoglou wants to do it at Spurs. He believes that night in Bilbao will just be the beginning if the right decisions are made behind the scenes to push the club on.
Everyone is waiting to see whether season three is truly better than season two or whether the main character will be killed off before it even starts, as Postecoglou feared. The problem is the main character at Tottenham Hotspur has always been Daniel Levy and the chairman will decide whether Premier League comfort is the ultimate aim or to back a man who dared and did.
