Tottenham still suffering from missing out on Bruno Fernandes & Jack Grealish

Few decisions have divided a fanbase as much as when Tottenham made the decision to replace the wildly popular Mauricio Pochettino with Chelsea legend Jose Mourinho.

Nearly 18 months into Mourinho's tenure, the mood at the club has soured, and if not for the pandemic, may even have turned chaotic if supporters were allowed into Tottenham Hotspur Stadium to vent their frustrations.

But whether you think Mourinho is past it or not, a 'serial winner' or no better than Tim Sherwood, the problems run deeper at the club, as captain Hugo Lloris passionately insisted last week.

The Frenchman was critical of Spurs' basics and fundamentals. But the club can boast one of the finest training grounds in world football, one of the best stadiums in all of sport.

That brings us to the personnel at Tottenham - the chairman, the board, the manager, the players. And there are two transfers which fell apart for Spurs that might have significantly changed the perceptions of all four groups.

Tottenham were heavy favourites to sign Jack Grealish from Aston Villa in the summer of 2018, weeks removed from Pochettino insisting that the club would have to 'be brave' to make another leap forwards.

But after a summer of courtship hoping that then-Championship side Villa would sell on the cheap, Spurs only submitted their first offer for Grealish on deadline day, and it was way below the asking price (because of course it was). They ended the window with no senior signings after the manager had been so public in calling for them.

While Grealish, now one of the ten best players in the Premier League - yeah, I said it - would have undoubtedly added real quality and fresh legs to the Spurs squad (which would have been opportune given this was when Dele Alli's fitness started to fall off a cliff), it may have nudged their history the wrong way slightly in the short-term.

The squeeze on Tottenham's players over the 2018/19 season led to their remarkable run to the Champions League final in the most dramatic circumstances, and signing Grealish may have disturbed the lack of balance in the squad in order to reach Madrid.

So that takes us to the following summer, where Pochettino was backed a little more. Spurs signed Tanguy Ndombele as their long-term successor to Mousa Dembele, Ryan Sessegnon and Jack Clarke as young players to mould and Giovani Lo Celso as another option between midfield and attack.

But the turnover was too late. To bridge the gap, Tottenham would have needed two or three more starters to keep Pochettino afloat, maybe one marquee signing to ensure they could prepare for Christian Eriksen's departure.

The high-profile missed opportunity came in the form of Juventus' Paulo Dybala, though it seems there were just too many complications trying to get him out of Turin for that to have been feasible in the end. But in the same week that the deal for Dybala lived and died, Spurs were close to bringing in someone else - Bruno Fernandes.

Missing out on Fernandes, who has since almost singlehandedly saved Manchester United from falling into the abyss, is one of the biggest 'what ifs' in Spurs' modern history.

Bringing in at least one of Grealish or Fernandes as goal and creative threats would have added to or replaced the output Eriksen maintained over his stay in north London, but getting the Portugal international to sign on would have done so without upsetting the Amsterdam applecart.

Fernandes might not have been able to immediately contribute enough to keep Pochettino in a job, but he would have provided a huge number of goals, assists and immeasurable energy for whoever he was working under. At the very least, Tottenham would have had three of the best players in the Premier League (alongside Harry Kane and Son Heung-min) plus another major floor and ceiling raiser.

With Eriksen currently on his way to winning Serie A with Inter and Dele fighting just to win his place back at Spurs, Mourinho has been picking and choosing a fresh flavour of the month just trying to make up the production and ease Kane and Son's load. Steven Bergwijn has provided zero goals and zero assists in the Premier League this season, Gareth Bale looked to have turned a corner last month, Lucas Moura looked to have turned a corner last week.

But none of these players are as good as Fernandes or Grealish.

Levy was unwilling to take more of a gamble with the man that had proved his worth more than anyone else in his reign at Spurs, perhaps more than anyone in his professional career. Yet he did find the courage to take such a risk and replace him with Mourinho. History will remember Tottenham's current chairman as a man who ultimately did good for the club, but his poor track record of calculated risks will keep him from universal approval.