Tottenham vs RB Leipzig is set up for Champions League magician Jose Mourinho to pull off one more trick

Mourinho hasn’t won Europe’s biggest crown for nearly a decade but this last-16 tie should bring out the best in him and his side

Tottenham Hotspur head coach Jose Mourinho (AFP)

In Diego Torres’ unflattering (though not inaccurate) biography of Jose Mourinho, the author addresses one key aspect to three drama-filled and, ultimately, poisonous seasons in Spain. Why Real Madrid hired him.

Before things descended into a political dog fight, those running the show at the Santiago Bernabeu were infatuated with Mourinho, the self-proclaimed, self-made winner. League titles in three different countries, a treble with Inter Milan and, of course, those two Champions Leagues. The European Cup had defined them as a club and who better to guide them to La Decima than the man who had it on a string.

Club president Florentino Perez and sporting director Jorge Valdano were also swayed by who he had beaten to get to that second title. In seeing off Barcelona in the 2010 semi-final, they believed he also had the codes to bring down their biggest rivals.

Of course, Mourinho knew of their infatuation and, like any good salesman, hammed it up as much as possible.

He became, in their eyes, a superstition: put your left sock on first; find a penny, pick it up; get Mourinho, get the Champions League. So they did. As Torres writes, “Continual success, successfully promoted is persuasion’s most seductive calling card.”

Yet here we are, approaching a decade on from the Portuguese’s appointment. Though Real Madrid did get their 10th, and three more after that, Mourinho is still waiting for his third.

There were three semi-finals in a row, and Tottenham’s round of 16 tie against RB Leipzig tonight will be his 15th appearance in the knockout stages. But while he was quick to remind everyone that he knows not of Spurs’ final woes after their defeat against Liverpool in Madrid last season - "I never lost a Champions League final!" – it was an inadvertent reminder it has been 10 years since success in a competition that he’ll tell you is in his blood.

It is easier to say in hindsight, but Mourinho, Real Madrid and the Champions League was doomed as a union beyond a clash of characters and philosophies. What success he had in the competition came as a gatecrasher, not as the establishment.

Porto had a previous European title to their name but were relative no-hopers in the modern era. Even an iconic club like Inter Milan could be painted as an outsider through similar lack of recent history in the competition, having last won it in 1965, and the kind of mismanagement through the 90s and 00s that had them pegged as basket cases.

Mourinho knew this, too, and it is why one of his early gripes with Real Madrid stemmed from insisting the club needed to lower their expectations. Naturally, Madristras took this as a slight. But it was more for Mourinho’s benefit. If they were to win, they had to win his way, and to do that they needed to lose that sense of belonging among the elite, which was never going to happen.

He encountered similar problems when he went back to Chelsea in 2013, failing to temper an aura of a team he had helped create. It did not help that they had claimed a Champions League trophy two years prior to his return. His gripes publicly were of players, like Eden Hazard, who thought they were too big to listen. Privately, it was a fear that the Belgian and certain others were too big to "obey”. Nor did the fans who were once his biggest advocates.

It was the successful campaign with Inter and that second-leg win over Barcelona which typified what Mourinho needs. Dominant opposition, down to 10 men through a controversial red card for Thiago Motta - the perfect cocktail of underdog and injustice. He wants his players to shed blood for him and, that night at the Nou Camp, they did. As Miguel Delaney wrote last November, some even spared teeth.

Mourinho hasn't won the European Cup for nearly a decade (Getty Images)

But the issue with Mourinho’s approach is the mentality he tries to cultivate is tough to replicate or even reinvent among top tier teams. That has especially been the case with modern players who take satisfaction from being the best rather than beating the best. That is not conducive to a tactical method that requires you to leave your strengths at the door, especially as an attacker.

The arguments that top-tier management has passed him by bear out in the anecdotes and in the numbers: a growingly frustrated figure alienating those around him and trying to hold on to former glories when his last win in a knockout tie came six years ago.

There is also a theory within the industry, one which has more than a kernel of truth, that Mourinho’s impact has diluted because so many people know what to expect from him. Thousands of stories, insights from those who have worked with him and, indeed, books like Torres’s have allowed all and sundry to piece together pages from his playbook.

Fans and players know what to expect from him too and that, certainly, has diminished the aura of the man. A once great method actor whose work has been pulled apart and reduced to a collection of catchphrases. You can imagine a punter stopping Mourinho in the street asking him to, “do the one about the first-half substitute!” A caricature now devoid of the "seduction", as Torres put it, that once made him so appealing.

However, while his three months at Spurs has been rife with those cliches – see also, “the blind faith in an out-of-sorts central midfielder” – there is a sense his shtick is going down better with a new, more receptive audience.

He has not totally won over the fans, but the players that will take him to the end of the season are listening. While talented, this squad is the least decorated he has worked with for a good 15 years. His medal haul far exceeds theirs as a whole and, just as it was at Porto and Inter, the spotlight shines brightest on the dugout for his presence than it does on the pitch.

Quite how that will manifest itself over the next two legs remains to be seen. But the ingredients are there.

RB Leipzig are legitimate challengers to Bayern Munich for the Bundesliga, sitting a point behind the league-leaders. They possess some of the most sought-after talent in Europe and are a model for the modern-day club. Spurs, by contrast, are much less slick administratively and, on the field, are shorn of Harry Kane and, now, Son Heung-Min for the foreseeable future.

It won’t be difficult for Mourinho to convince his players they are underdogs who need to trust him implicitly. More importantly, those players have no reason and no option not to do so.