Mauricio Pochettino faces a defining moment as the Tottenham boss aims to joins the managerial elite by masterminding a famous Champions League triumph against Juventus on Wednesday.
Long regarded as one of the sport's brightest young managers, Pochettino can use this season's Champions League to reach the rarified air inhabited by the likes of Pep Guardiola, Jose Mourinho and Diego Simeone.
Like his former Argentina team-mate Simeone, Pochettino is coveted by some of Europe's biggest clubs.
But while Simeone has defied the odds to lead Atletico Madrid to La Liga and Europa League titles, as well as reaching two Champions League finals, Pochettino is still waiting for his breakthrough moment.
Despite earning plaudits throughout his nine-year managerial career with Espanyol, Southampton and now Tottenham, the 46-year-old has failed to lead any of his clubs to a major trophy.
Clearly, silverware isn't the only measure of a manager and no one would doubt Pochettino overachieved at Espanyol and Southampton given the lack of financial backing available.
Although Tottenham have greater resources than either of Pochettino's other teams, they largely steer clear of the huge fees paid by their top four rivals in the Premier League.
Since arriving in north London 2014, Pochettino has deftly navigated those constraints to turn Tottenham into a genuine top four force after years of underachievement.
But the crucial black mark on Pochettino's CV remains his failure to push Tottenham across the finish line when they have been on the brink of landing a trophy.
Having reached the League Cup final in 2015, Pochettino's side slumped to a disappointing 2-0 defeat against Chelsea, while in 2016 a late-season swoon allowed Leicester to coast to the Premier League title.
A vital loss at West Ham cost Tottenham dearly last season when they were unable to keep pace with eventual champions Chelsea, who also knocked out their rivals in the FA Cup semi-finals.
Tottenham's struggles in away games against their main rivals have been a constant problem throughout Pochettino's reign, dooming them to also-ran status in this season's title chase.
But Tottenham's Champions League exploits over the last few months suggest any inferiority complex is being eroded at last.
- Football is a joy -
That certainly seemed the case when they crushed European champions Real Madrid 3-1 at Wembley with a vibrant display that showcased the best of Pochettino's high-tempo philosophy.
That impressive result came after a draw in Madrid and recovering from two goals down to draw 2-2 in the last 16 first leg against Juventus was another step in the right direction.
With Tottenham hoping to reach the Champions League quarter-finals for the first time since 2011, eliminating the Italian champions would be another step towards the top table for Pochettino.
His appetite for success is driving him on and, after admitting he once thought of quitting management by the time he was 50, the Argentine now plans a long career on the bench.
"When I started as a manager I was 36, I said, 'Okay, I will be a manager and my limit is 50'," Pochettino said.
"Now, I don't know if I will be longer like Roy (Hodgson) or (Sir Alex) Ferguson or Wenger or maybe I will stop before.
"When I watch football and the manager always criticises everyone and sees the phantom and tries to defend himself and fight with you and fight with the fans and fight with this. That is no life.
"I want to improve and try to enjoy doing my job but if I am going to suffer or create drama in my life, I would prefer to go away.
"Football is a joy. The most quiet I am is when we are going to compete. It's not a drama. For other people it's different but for me football is not a drama - it is a joy."