After Tottenham acquired Lucas Moura from Paris Saint-Germain at the end of the January 2018 window, Spurs went 18 months without making another signing. This came despite two very public - and out of character - pleas from Pochettino to then-chairman Daniel Levy.
At the end of the 2017-18 season, the Argentine pulled no punches at his final press conference heading into the summer, saying: "If we want to be real contenders for big trophies, we need to review a little bit the thing. We need to create dreams that will be possible to achieve. Maybe we are a bit disappointed and frustrated because now we are close [to trophies].
"I think Daniel is going to listen to me, of course. You need to be brave. Being brave is the most important thing and take risks. I think it’s a moment that the club needs to take risks and tries to work, if possible, harder than the previous season to be competitive again, because every season will be more difficult."
Spurs' only sign of any activity in the summer of 2018 was a derisory bid made for Jack Grealish, offering £4m plus academy graduate Josh Onomah, believing Aston Villa were on the brink of financial disaster. In fact, the West Midlands club had just received fresh investment and laughed them out the door.
Levy and Co at the time insisted the budget was there for Tottenham to bolster the squad despite their delayed move to the new billion-pound Tottenham Hotspur Stadium, but suggested at a meeting with the supporters' trust that transfers were actually quite difficult to pull off. That was an admission of failure to Pochettino, his players and the fans. It was also the first sign that this regime was not ready to make that leap to a truly club.
Pochettino's Tottenham ran on fumes for the entire 2018-19 season having made one senior signing across their last two transfer windows, failing to add to what was an already thin squad while missing the chance to shift other players when their concentration started to wane. That's why reaching the club's first-ever Champions League final was even more of a miracle, but the circumstances around Spurs getting there left Pochettino even more drained, and he intimated he would quit if they did indeed become kings of Europe.
Shortly prior to their famous comeback against Ajax in the semi-finals, Pochettino again warned that there was no point in Spurs investing so much in a new stadium if they were going to neglect the squad again: "When you talk about Tottenham, everyone says you have an amazing house, but you need to put in the furniture. If you want to have a lovely house, maybe you need better furniture. And it depends on your budget if you are going to spend money. We need to be respectful with teams like Manchester City or Liverpool who spend a lot of money.
"We are brave, we are clever, we are creative. Now it's about creating another chapter and to have the clear idea of how we are going to build that new project. We need to rebuild. It's going to be painful."
Spurs signed Tanguy Ndombele, Giovani Lo Celso, Ryan Sessegnon and Jack Clarke during the summer of 2019, but that wasn't enough to repair the damage of the previous 18 months and they have been playing catch-up in the market ever since. Every window has proven too reactive and, at times, one window too late.
Pochettino was sacked five months after the Champions League final, with the club pivoting to a 'win-now' strategy under Jose Mourinho. It didn't go as planned.