A fresh-faced and seemingly re-energised Mourinho arrived in North London in November 2019 to a huge amount of fanfare.
Levy was reportedly wowed by what the Portuguese boss had described as his ‘brand new methods’ which would take Spurs from the nearly-men they were under Pochettino to perennial winners.
He departs less than two years later in almost exactly the same manner he did from Manchester United and from his second spell at Chelsea – beleaguered, rattled, irritable and completely and utterly out of ideas.
He has gone from being “in love” with the squad he inherited upon his arrival to seemingly falling out with each and every one of them, alienating some of the most talented players at the club.
Mourinho himself may have recently described the situation as “same manager, different players.”
But in reality there is a trend following him everywhere he goes – and it is not a positive one for the Portuguese coach.
The truth is that even from the start he just did not seem a good fit for Spurs.
The fans were highly suspicious of a man who was such an icon at their bitter rivals Chelsea, and one who had failed so miserably in his last few months at United.
His name was never sang inside the stadium when supporters were still allowed in, and a flag of Pochettino loomed large for weeks following his dismissal.
Although results were ok at the beginning the spectators were never truly won over, and one can only imagine the toxic atmosphere there would have been inside the ground had they been permitted this season.
The treatment of two of Spurs’ most exciting players – Dele Alli and Gareth Bale – is also a massive mark against Mourinho’s name, and surely any manager worth his weight in gold would be able to get more out of the two than he did.
And by the time he began to even fall out with the ever-professional Toby Alderweireld, it was clear that the damage was way beyond repair.
Tactically, despite his promises to Levy, Mourinho also appeared yesterday’s man.
Even at the start of this campaign – when Spurs were briefly top of the Premier League heading towards Christmas – they were desperately over-reliant on moments of magic from Harry Kane and Son-Heung Min.
And they never once played anything remotely resembling the attractive, free-flowing, high-pressing football that we saw under Pochettino.
Mourinho was one of the highest-paid managers in the world at Spurs, yet it is hard to think of one single way in which the team improved during his spell, and that is perhaps the most damning part of it all.
Spurs are currently in the process of opening up season ticket renewals – and Levy may well have felt the only way to fill the 62,000 seater stadium was to get rid of Mourinho now before it was too late.
That being said, Mourinho is not the only person to blame for the mess Spurs find themselves in.
The cracks were beginning to show long before Pochettino was given his marching orders, and the reinvestment the team so desperately needs has yet to happen.
A number of key members of the squad need to take a good long look at themselves and their attitudes, and some are simply no longer good enough for a side who should be at least challenging for the top four.
But ultimately, try as he might, Mourinho has very few excuses as to why he was unable to get a squad with such talent doing better, and his results record is simply shocking.
Where both he and Spurs go now is anybody’s guess, especially with the shadow of the European Super League threatening to completely transform football as we know it.
But the history books will look back at Mourinho’s brief reign at Spurs as one of the most catastrophic errors ever made.
Levy was right – his decision will be remembered forever.
Not, however, in the way he would have wanted.