Tottenham Hotspur, for all their efforts to banish their silverware stagnation, have come unstuck on more than one occasion.
In fact, Daniel Levy even recently took ownership for some of the questionable decisions clearly motivated by a desire to get their trophy-dodging monkey off their back, speaking at the recent Fan Forum: "I had gone through a period where we'd almost won. With Mauricio we went through some very good times. We didn't quite get there but we came very close and we had a change in strategy. The strategy was 'let's bring in a trophy manager.
"We did it twice and look you have to learn from your mistakes. They're great managers but maybe not for this club."
Such admittance to failures of the past is admirable, but made far easier when Ange Postecoglou has already returned the feel-good factor to north London. It was always bound to be well-received, given the positivity that the Australian's tenure is bringing.
Therefore, the 62-year-old businessman cannot be allowed to be completely expunged for his past failures, which have doomed the fanbase to years of ridicule.
One such example is his appointment and subsequent treatment of Jose Mourinho, hiring the legendary Portuguese tactician with the record of having won a trophy with every club he had overseen. Then, despite the rocky nature in which they reached the EFL Cup final in 2021, the decision to sack the now-AS Roma man before playing it was ludicrous.
Admittedly, his was a tenure that hardly screamed of forging a dynasty in N17…
Who did Jose Mourinho sign for Spurs?
The signings of the 60-year-old were enough to suggest that the former Chelsea boss had little plans of sticking around for the long haul, as he sought to acquire proven talent to perform instantly.
Stars like Pierre-Emile Hojbjerg, Giovani Lo Celso and Sergio Reguilon were all proven in their own right, and yet the latter two struggled to impress in their first few years. Even the loan acquisition of Gareth Bale, bringing him back to north London seven years after his world record departure, screamed of that 'win-now' mentality that Levy mentioned.
However, arguably the biggest disappointment of all these names was the signing of Matt Doherty, who marked a shrewd initial capture from Wolverhampton Wanderers.
The Republic of Ireland international had shone at Molineux for many years, but able to capitalise on a dwindling contract, he was brought in for just £15m. Republic of Ireland boss Stephen Kenny lauded the move initially, clearly unaware of the misfortune that was to come. He noted: "It's certainly an interesting move for Matt, who has been a tremendous servant for Wolves. He is one of the best full-backs around, he will be very much in the frame to play.
Giovani Lo Celso (Real Betis)
€32m (£27.7m)
Steven Bergwijn (PSV Eindhoven)
€30m (£25.9m)
Sergio Reguilon (Real Madrid)
€30m (£25.9m)
Matt Doherty (Wolverhampton Wanderers)
€16.8m (£14.5m)
Pierre-Emile Hojbjerg (Southampton)
€16.6m (£14.3m)
Joe Rodon (Swansea City)
€12.10m (£10.4m)
Joe Hart (Burnley)
Free
"His number of assists, plus he's goalscoring full-back, if your full-back is scoring and creating goals it's a real asset. I think it's great value and a great deal for Tottenham."
However, provide offensively he did not, with first-team opportunities limited despite having recorded eight goal contributions from right-back in the league for the Old Gold the year prior.
Just two Premier League assists all season merely scratched the surface of his mediocrity during that debut term, with the 31-year-old's lack of defensive awareness hardly blending well with Mourinho's steadfast and solid system. Journalist Gareth Davies would outline his surprise at just how bad the flop managed to be under such a defensive boss: "Almost impressive at this point that no matter the opposition, no matter the situation, Matt Doherty is absolutely useless."
Therefore, it was a surprise to see the defender very nearly survive through the tenures of another two permanent coaches before meeting his north London end.
Why did Matt Doherty leave Spurs?
The manner of Doherty's exit was extraordinary, and only emphasised the torrid lack of forethought shown by the club.
Having been lambasted in snide fashion by Antonio Conte earlier in the season, describing a system without the full-back as "the right way to start the game", it seemed set for him to spend the rest of the 2022/23 season on loan with Atletico Madrid.
With all the paperwork signed as the former Bury loanee headed to Spain, Spurs realised that with Djed Spence also leaving temporarily for Rennes they had used up their eight outgoing loan slots.
As such, they had to agree to mutually terminate his contract, and he was unveiled as a new Red and Whites player soon after on a free transfer.
How has Matt Doherty played since leaving Spurs?
It is fair to say that, since departing England, Doherty has hardly recaptured the form that saw the Lilywhites first seek to sign him.
After all, he would make just two La Liga appearances for the Madrid outfit, neither of which were starts, before moving once again.
Having spent ten years of his career with Wolves, it only made sense for him to return to the Midlands during their fiscal hour of need. With Julen Lopetegui frustrated regarding the lack of transparency of their finances, the 37-cap ace marked a shrewd free transfer for them to bolster a threadbare squad that was somewhat gutted over a tough summer window.
However, it's fair to say that his performances in the league have been nothing short of abysmal, with a 6.40 average Sofascore rating suggesting that it has been far from the romantic return he likely envisioned.
Even journalist Dean Jones highlighted his surprise with the lack of minutes Doherty is managing for a relegation-threatened side. Speaking to GIVEMESPORT, he said: "You felt at that point, there must be a specific plan for him within this team. If he was going to return, he knew where he was fitting in, but he hasn’t had that many minutes. I think that that is quite a surprise, to be honest."
Whilst Mourinho's tenure already feels long-forgotten given the bulk of his acquisitions are far from the first-team, this is one that marked a particularly frustrating deal due to the manner of his exit.
Allowed to leave for free due to a lack of faith from the manager, the hope will be that under Postecoglou they can remove such foolish moves from their repertoire and seek to build towards a brighter, more incisive future with the former Celtic boss spearheading such a charge.