Jose Mourinho, Tottenham Hotspur
Jose Mourinho looks on during Spurs FA Cup match against Southampton. Will Oliver/Shutterstock.

Jose Mourinho has rarely been considered the optimist among his managerial peers, but he has a right to be disgruntled with his fortunes—or lack thereof—during his first term as Tottenham Hotspur chief.

The Special One’s reputation appeared at an all-time low when he was relieved of his duties at Manchester United in December 2018. It was his first such dismissal–that is, if leaving a club “by mutual consent” is considered to be a different strain of departure.

Expectations might have been lowered in north London as a result, but exceeding the 14th position that Spurs occupied when he took the reins won't be the only measurement of success. The task of succeeding Mauricio Pochettino at Tottenham was massive, not least because Mourinho took over in November, midway through the campaign and without a summer transfer window to stamp his imprint on the squad.

It's the task of doing more with less—as Pochettino did for years—that is more necessary now than ever before. Spurs announced on Tuesday that Son Heung-min is to undergo surgery on a fractured arm this week, robbing the side of its second-most reliable scorer after England captain Harry Kane, who was already sidelined until May.

In typical Mourinho fashion, the manager told reporters the situation “couldn’t be worse.” Indeed, the Portuguese is yet to see a fully fit squad during his three months in charge, but Spurs were nonetheless unbeaten in seven games before their loss to RB Leipzig–only their sixth in 21 outings under his tutelage—a record not to be sniffed at considering the setbacks.

The absence of Tottenham's best finishers was only too noticeable during the 1-0 defeat at home to RB Leipzig on Wednesday. Spurs trail in their Champions League last-16 meeting after the first leg, and it's clear the void in attack isn't going to be solved overnight.

While he may sound despondent in his quotes to the media, one could imagine it's the kind of challenge Mourinho would relish, as it would be a feat in itself if Spurs were to clinch a Champions League quarter-final slot next month.

Despite the in-season woes, and chairman Daniel Levy’s historical reluctance to spend vast sums in the transfer market, there’s a growing confidence that Mourinho will be backed in the summer. Perhaps not to the extent he was at United, Real Madrid or Inter Milan, but enough still to resurrect the top-four contention in the Premier League that became commonplace under his predecessor.

Spurs did already smash their transfer record to sign Tanguy Ndombele from Lyon last summer—prior to Mourinho's arrival—but the January moves for Benfica's Gedson Fernandes and PSV winger Steven Bergwijn were encouraging expenditures. The club also completed the permanent signature of Giovani Lo Celso last month following a successful first half of the season on loan.

Granted, those transfers come with the caveat that Christian Eriksen was sold to Inter Milan for a cut-price $22 million, but even that situation was handled well by the manager as the Dane neared the end of his contract and appeared more than prepared to leave North London.

Regardless of injuries hindering his plans, supporters will expect solutions between now and May. That’s the reason one hires a manager of Mourinho’s pedigree, to find answers where others would remain staring blankly at the chalkboard.

Jose delights in proving his doubters wrong, and there’s maybe no greater opportunity to do so than with the odds piled against him at the “smallest” club he’s managed since leaving Porto.

The 2004 Champions League triumph with the Dragons remains his biggest feat for that reason, a prime example of achieving beyond his means in a competition regularly ruled by the same titanic powers.

His 20 major trophies speak volumes, that much is granted. But as with any tactician at a top club, some of that must be attributed to the players he inherited and the size of the teams managed.

Even in a down year compared to recent seasons, Spurs have the opportunity to lift several trophies. Tottenham are due to face Norwich City in the fifth round of the FA Cup in March, presenting them with a second chance at silverware–their most realistic one at that.

Between the FA Cup, Champions League, and the single point distancing them from fourth-place Chelsea in the Premier League, there’s cause for optimism, particularly with a figure like Mourinho in the dugout, and particularly with 5th-place potentially grabbing a 2020-21 UCL spot after Manchester City's two-year UEFA ban.

There’s been a sense for some time now that Mourinho’s talents as an elite-level manager are waning. But a chance has arisen to remind the world of his ability to thrive, in what could end up being perhaps not the most glittering, but the most impressive campaign of his career to date.