Walking out of Chelsea with the club hovering precariously above the relegation zone, Mourinho's squad was in turmoil, the culture was toxic, and fans labelled some of the stars 'rats'. It was fast-becoming one of the worst title defences of all time and as much credit as Mourinho had in the bank, it had all gone so badly wrong.
After a period of stabilisation under trusted interim boss Guus Hiddink - where they rallied to finish 10th - enter Antonio Conte, stage right.
The Italian got straight to work, bringing a passion, energy and desire that was a major void of the end of the Mourinho era. Fans and players alike were having fun again and soon they couldn't stop winning.
Antonio Conte (right) finds himself trying to clear a mess left by Jose Mourinho (left) again
Tottenham failed to kick on under Mourinho and have not been able to improve since his exit
That is the hope for Tottenham now. To win and win and win and never stop.
In reality this is a seismic task for Conte as he looks to clear up another mess from Mourinho - with successor Nuno Espirito Santo barely being able to dip a toe in the water having been sacked after 17 games.
'I hate to say it but what a signing this is,' former Chelsea captain John Terry said.
'The players will love Antonio and his staff. Be ready to go to work Harry (Kane).'
Tottenham need a culture change as well as a playing identity. Tottenham need misfiring stars to believe in themselves again and Tottenham need a team that fans can rally behind.
If his clear-up of Mourinho's bitter end at Chelsea is anything to go by, Conte will hope history repeats itself in north London.
One of the first things Conte is likely to implement is a change in formation.
When he turned up at Chelsea he stuck with a 4-2-3-1 - the formation used by Nuno Espirito Santo in his doomed 17-game spell at Spurs - system but soon realised it was flawed for his philosophy.
It took Chelsea going 3-0 down to Arsenal for Conte to say enough is enough. Off came Cesc Fabregas, on came Marcos Alonso and Chelsea's 3-4-3 future under the Italian was born.
'It's not easy to adapt to new methods, a new philosophy, and also to work very hard,' Conte said at the time. Tottenham's players best be equally receptive or risk finding themselves frozen out.
Conte has an obsession with maximising the role of wing-backs and both Alonso and Victor Moses can attest that Conte was the best thing to happen to their careers.
Emerson Royal (left) and Sergio Reguilon (right) are set to flourish based on Conte's record
Both were viewed as average to good players but under the tutelage of Conte, and with him trusting them both implicitly, they became some of the best full-backs in the country.
That should come as music to the ears of Emerson Royal and Sergio Reguilon.
The former Barcelona and Real Madrid players both boast blistering pace and have typically looked more comfortable attacking than they have defending.
Ben Davies, as he often does for Wales, is more likely to slot inside as a centre back option, Matt Doherty has work to do after falling out of the side and so Reguilon and Emerson can expect significant roles under the Italian.
There are examples at Inter Milan, too. Achraf Hakimi stepped up to be one of Europe's finest wing-backs under Conte while Ashley Young breathed new life into his career with the help of the Italian.
But lets focus on Chelsea, his title-winning 2016-17 season and how Alonso and Moses elevated.
The duo combined for 10 goals and seven assists in 2016-17. While this season is still in its infancy, Reguilon and Emerson have combined for zero goals and two assists.
Marcos Alonso (right) became a league-leading talent as Conte rid Mourinho's woes at Chelsea
Nuno's approach simply stunted the potential of both Emerson and Reguilon and Conte will likely have looked at them both and seen huge potential he can harness.
There are other elements that will be demanded of his wing-backs, it will be exhausting, they will need to become fitter than ever before - Conte will make sure of that.
Stories emerged at Chelsea of Conte overhauling the food options after training and before matches and while there was initial discontent the results showed a fitter and healthier squad which soon found themselves winning.
Apply themselves in the correct way and Tottenham's full-backs could be about to get the shot in the arm their career has been crying out for.
It's fun in the beginning, getting Mourinho as your manager.
The sarcasm can be seen as funny, club photographers capture big smiles in training, but eventually his cold nature is impossible to defrost and the winter of discontent is plain for all to sea.
Axed on the lead-up to the Carabao Cup final Mourinho, who was not the most popular appointment, can take the fun out of it and Conte, while being equally explosive when his reins come to an end, will inject some passion and energy into a club that is sleep-walking down the table.
Having Nuno follow Mourinho was another appointment few fans found themselves able to get behind. Nuno's manner is much more reserved, rarely does he expand on his points and he's a far cry from some of the box-office managers that run the Big Six clubs.
Passion is the buzzword around Conte (middle) and he can channel the spirit he had at Chelsea
Bringing in someone of Conte's stature will immediately excite players, Harry Kane chief among them, and a new manager means a fresh chance to make an impression.
At Chelsea Mourinho left with the Blues one point above the relegation zone. The players looked incredibly poor. The culture was not right. Standards had slipped.
'Palpable discontent' was how then-director Michael Emenalo described it. Conte had a lot of work to do.
Conte prides himself on trying to create a familial atmosphere at the clubs he is at, one where everyone is seen pulling in the same direction for greater good. He's big on team-building and is one of the master man-managers in the game.
Winning helps but it is no surprise that his first interview as Tottenham boss specifically included the word 'passion'.
'My coaching philosophy is simple,' Conte told SpursTV. 'To play good football, attractive football for our fans with passion. Fans deserve to have a competitive team with a will to fight.'
There has been a culture issue at Tottenham since the final days of Mourinho's Spurs tenure
HAZARD SHOWS SON CAN SHINE
The first thing to note is that Hazard, under Mourinho, was a unanimous Player of the Year in the 2014-15 title-winning season.
But his form dramatically declined the following season and Hazard was labelled as one of three 'rats' who contributed to Mourinho's demise, and ultimate sacking.
His stock among supporters had plummeted, he was booed for supposedly downing tools and patience was wearing thin. His form, too, had massively dropped off.
What Conte did immediately when he came in - and Hazard has had gripes since about Conte's methods - was make Hazard believe he was the best in the world again.
The Belgian flourished alongside Diego Costa and finished 2016-17 with 17 goals and seven assists, coupled with a Premier League winner's medal and Chelsea's Player of the Year award.
The upturn is something that Son Heung-min can look at and become excited about.
Son Heung-min (centre) has struggled to click into gear but Conte can revive him once more
As much as Conte's principles are predicated on defending and tightening up at the back, creativity and flair remains important.
If he elects to play a 3-4-3 then Son can occupy a familiar wide role, likely out left of Kane, and he would form a key part of what would be a three-pronged attack.
Say Conte differs slightly and goes for the 3-5-2 he liked so much at Inter Milan, Son alongside Kane would likely be devastating.
Having just signed a new five-year deal at the club Son is a piece that Conte can build the rest of the puzzle around.
His relationship with Kane has looked non-existent this season and so both players' stats have suffered as a result.
In 13 games so far this season, Son has four goals and just two assists.
In 2020-21 his stat-line read 51 games, 22 goals and 17 assists.
Son works hard which will endear him to Conte and as one of the most passionate players in the squad he is sure to become a favourite of the Italian.
When Hazard looked to be channeling in the wrong direction Conte breathed new life into him and put him back on the right path. Don't be caught by surprise if Son gets the same treatment.
Conte's passion revives out-of-form players and attackers can flourish as part of his systems
ULTIMATE GUIDE TO DEFENDING
When he posed for the cameras upon arriving at Chelsea, Conte said: 'The coach must be a tailor to find the right suit for his team.'
It became a popular soundbite amid the discontent sewed by Mourinho in his final days.
Defeat at Leicester in December 2015 was a ninth loss in 16 games for Chelsea under Mourinho. Only Swansea, Norwich, Sunderland and Aston Villa sat below them in the table.
Mourinho was left 'ashamed' and said they had 'no chance' of making the top four. Roman Abramovich had heard enough and Mourinho was gone. All blame was being shoved onto his players and it was becoming desperate.
Guus Hiddink steadied the ship before Conte came in and catapulted them to the next level.
Much of that success in clearing up Mourinho's mess was down to defensive solidity and after the switch to a back three at Arsenal, they conceded just 24 goals in the league for the remainder of the campaign.
For context, Spurs have already shipped 16 goals in the Premier League this season.
Mourinho (left) has been viewed as a defensive manager but not in the mould of Conte (right)
Tottenham's defenders, just as Chelsea's did five years ago, are about to get the perfect tutor in Conte.
Cristian Romero and Eric Dier have looked less-than-convincing as a partnership and it remains to be seen who will prove the third component of a new-look back three, perhaps Japhet Tanganga, Davinson Sanchez or Ben Davies.
Remember too that no team in Serie A conceded less than his Inter Milan team in 2020-21 - en route to their first title in a decade.
Come the end of his time at Chelsea, Mourinho's team were leaking goals in near comical fashion. It got to the point where he was at odds trying to explain it.
In Conte Spurs will have a manager who has a track record of making average defenders play beyond their believed capabilities and much of his focus on the training ground will be in drilling a shape and a defensive identity that has brought him success wherever he has gone.
The period which many view as the moment they won the league saw Conte's Chelsea take 10 clean sheets from 13 matches. The sense was growing that this defence could not be breached - it was a champions mentality.
Cristian Romero (left) and Eric Dier (right) will get a masterclass in defending from Conte
UNLEASH THE ATTACK
In the season Mourinho won the league title at Chelsea in 2014-15, Chelsea scored a total of 73 goals.
Under Conte, a new-and-improved Chelsea scored an impressive 85 goals, only Tottenham, ironically, beat them out to top spot in that ranking that season.
Mourinho was cutting in his criticism and attackers soon stopped responding. Conte can be harsh but often he is the one backslapping, whooping and hollering his players to make them feel like the best in the world.
And so it is no surprise Kane is enthused by the 52-year-old's arrival given his proven track record of success.
Diego Costa, before it ended sour over text, thrived under Conte and the Italian took an out-of-shape Romelu Lukaku at Inter Milan before turning him back into a £98m talent.
Kane will be key. The striker has been frustrated by the club's lack of ambition and tried to leave the club in the summer as a result.
But Conte's arrival is certainly viewed as a positive by the Tottenham striker.
Harry Kane (left) is excited to play for Conte (right) and it is no surprise given his track record
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