There's a certain irony to the fact that Tottenham Hotspur need to take their biggest gamble on a new manager at a time when chairman Daniel Levy is in desperate need of a sure thing.
Those who know the 61-year-old say that while he is not a gambler, Levy has often been willing to take a calculated risk and now, more than ever, those calculations need to be spot on as he looks to select not only the club's next head coach and director of football but also shape the way forward for Spurs.
The Spurs chairman is now set to speak to those potential managerial appointments already in jobs after the club drew up its shortlist and the eventual successful candidate needs to be a transformative one.
READ MORE: What Daniel Levy did after Tottenham loss, what Hugo Lloris said and the chairman's manager call
For Tottenham's first team needs to be ripped up and started again. Levy's recent appointments, lurching from one style to another, have all built upon the foundations of what has come before since Mauricio Pochettino's arrival in 2014 rather than creating anything new, instead merging into a messy hybrid of a club without any real direction or identity for the fans to connect with.
With the need for Levy to appoint both a head coach and director of football as well as Scott Munn's arrival as chief football officer this is a huge opportunity to Tottenham to become whatever they want to be on the pitch.
Levy listens to a select few people in the game - and occasionally doesn't - and he will need advice from those with football knowledge on what comes next. Following Fabio Paratici's resignation after his 30-month ban in Italy, later extended globally by FIFA, was upheld due to his claimed involvement in the problems at Juventus, a strong football voice in the Tottenham boardroom has been lost.
Tottenham have categorically denied suggestions from outside the club that Levy has received advice with this managerial search from the Sportsology Group, who are run by executive chairman Mike Forde, previously Chelsea's director of football operations for six years. The group were credited with helping Manchester United in an advisory role in selecting Erik ten Hag as their new manager.
Despite being shown in a recent photo with Levy, Spurs also maintain that Munn will not begin work until July 1 when his gardening leave at The City Group ends. The north London club faced a similar situation with Paratici in 2021 although his earlier involvement and influence was clear on their managerial search back then.
Due to the pressure around the club, Tottenham are faced with the awkward predicament of potentially appointing a new head coach before they name a new director of football, which is not the ideal way round for that system to work.
The aim is understood to be the club searching for both simultaneously and Spurs must make sure that they appoint two people to those roles who are aligned in their football beliefs and both must be given free licence to implement their philosophy as they see fit, not be guided by others, and not simply build upon what has come before.
That is where the gamble lies, particularly when it comes to the age category and experience - or lack of - when it comes to many of the more exciting managerial candidates around.
football.london understands that Paratici had former Spain and Barcelona boss Luis Enrique, ex-Bayern head coach Julian Nagelsmann with whom contact has already been made, Brighton manager Roberto De Zerbi and Porto boss Sergio Conceicao among his shortlist to replace Antonio Conte.
Post-Paratici Spurs have also been looking at a range of relatively young candidates in an attempt to replicate what they did in pushing the club on with a fresh identity with Pochettino in 2014, something that has been replicated and taken on with silverware at Arsenal with Mikel Arteta.
Some of those candidates looked at and researched include Nagelsmann, De Zerbi, Feyenoord coach Arne Slot, Burnley manager Vincent Kompany, Leverkusen's Xabi Alonso, Sporting's Ruben Amorim as well as an older but no less dynamic candidate in Celtic boss Ange Postecoglou.
Critics might suggest there are a lot of "flavour of the month" names among those coaches and plenty of untested managers in a major European top flight league. That would be where the appointment of an experienced director of football would be key.
It's also worth noting that both Alonso and Amorim in particular use a back three, as does Nagelsmann occasionally, which would help utilise some of the current Spurs squad but might not go down too well with the fans who have grown disillusioned with the formation. Those coaches might in turn argue it's more about the system and approach than the formation that dictates what those supporters will see on the pitch.
Caretaker boss Ryan Mason, at just 31-years-old, has also thrown his hat into the ring since taking on the job as acting head coach from Cristian Stellini.
If Spurs do look to replicate the Arsenal way, who in turn are only replicating the Pochettino way with smarter recruitment, better backing and the silverware to boot, then Mason technically would be the closest thing to an Arteta clone, having been an assistant only before.
Mason is a Pochettino disciple as well, although being a decade younger than Arteta and with so little experience, it would be another big risk and whether a frustrated fanbase would simply see such an appointment, rightly or wrongly, as unambitious is another thing. Mason could well argue that he is better placed than any of the other young names currently in consideration because of his knowledge of the club and the current players.
Just how many of those current players will be at the club next season though is another matter.
A regular social media occurrence after defeats in recent seasons has been tweets or posts showing just how many Spurs players remain in their team from seven or eight years ago compared to the lesser numbers of the overhauled and triumphant opponent.
It's a Tottenham squad packed with familiar and often-criticised players. Many are the players for whom the club means the most, but they are also the first to be pointed at when things go wrong as a visible constant of seasons without reaching the next level.
One of those long-serving players, the one nobody wants to see leave, is Harry Kane. Will he want to be part of any rebuild and would he have the patience to start again with no guarantees a new set-up would work?
Either way, the next head coach and his director of football must be given the chance to create something new and that is likely to mean Levy handing over more control to Munn and those below him when it comes to on-pitch matters.
Munn is expected to be the closest thing the chairman has ever had to a number two during more than two decades at Tottenham and his arrival was announced with the clear statement that the Australian "will take charge of all footballing departments".
A radio interview with former Spurs' Head of Elite Potential Identification David Webb this week did not reflect well on Levy when he was asked whether the chairman ever said no to potential signings.
"Yes. There was cases when I was at Spurs we had players in the building that we should have potentially signed that would have helped [Mauricio] Pochettino at that time, that didn’t go through through various aspects," Webb told talkSPORT. "There were questions being raised that sometimes if we had acquired that player at that certain time it could have steered Tottenham in a different direction."
Levy needs to allow others to have their chance now in deciding on the pitch matters. For all of his success off the pitch, when it comes to the team and what they have failed to achieve on it during the past 22 years, the chairman's football decision-making has been inconsistent at best. The appointment of Munn appears to be one step towards giving a fresh voice to what comes next if Levy can truly step back and allow others to take the controls.
It's a turbulent time at Tottenham and confidence in the club and the ability of Levy to steer the ship in the right direction has fallen to a new low. There are positives to be grabbed from change though as long as that change is right. It's time for Levy to take a calculated gamble. It's time to set a new course.
READ NEXT:
- Fabio Paratici - The man who can no longer tell Daniel Levy what to do at Tottenham
- How Julian Nagelsmann would transform Tottenham and help Daniel Levy after Stellini exit
- Tottenham in Romaine Mundle contract race with first team promotion after Herbie James transfer
- The incredible list of ex-Tottenham stars playing in a remarkable fundraising match next month
Tottenham complete transfer for talented young defender and striker signs new deal with the club
