1. Mauricio Pochettino 2014-2019
Mauricio Pochettino is unequivocally Tottenham’s best manager from the last decade, if not the best ever. With an unbridled devotion to providing youth with a chance to flourish, Pochettino nourished and developed the likes of Harry Kane, Dele Alli, Christian Eriksen, to name just a few.
He was appointed manager on May 27, 2014. Less than a year later, Tottenham made it to the League Cup Final where they lost 2-0 to Chelsea. It was the first cup final Tottenham had appeared in since winning the League Cup in 2008.
Tottenham qualified for the Champions League in all but one of his five seasons in charge. His first campaign saw Spurs finish fifth in the Premier League. Tottenham finished in 3rd, 2nd, 3rd and fourth in the four subsequent seasons under his guidance. He also led Spurs to two successive FA Cup semifinals — in 2016/17 and 2017/18 — and a League Cup semifinal in the following season, 2018/19.
Of course his primary claim to fame is taking an injury-riddled Spurs side to the 2018-19 Champions League Final. Coming back to defeat Ajax in the semifinal thanks to Lucas Moura’s last-minute heroics will go down as one of the most epic moments in club history.
Pochettino was renowned for implementing an incredibly high energy press, which garnered almost immediate results. He elicited the best from his young side and will go down as one of Tottenham’s best managers of all time.
The messiah won 159 of his 293 matches at the helm, a 54 percent winning rate. That’s only one percent lower than Villas-Boas in a much larger sample size.
The only knock on his CV is falling at the last hurdle numerous times. For all his greatness, Pochettino was never able to win an elusive trophy, a regrettable blemish on an otherwise immaculate CV.
Wish he would take the current opening.