The Spurs chairman has overseen some big-money departures during his time in north London, including the sales of Gareth Bale, Kyle Walker, and Luka Modric among others.
He has also opened the purse strings at times to sign the likes of Christian Romero, Richarlison, Tanguy Ndombele, and Moussa Sissoko, but to name a few.
Whilst not every transfer has been perfect, he has played some blinders in the market and one player he pulled off a masterclass with was right-back Kieran Trippier.
His compatriot’s move to Manchester City in 2017 opened up a space in the starting XI and Trippier, who currently plays for Newcastle United, grasped his opportunity with both hands as he nailed down the position as his own.
The gem, who was previously dubbed “underrated” and a “warrior” by England manager Gareth Southgate, averaged a superb SofaScore rating of 7.25 in the 2017/18 campaign as he played 24 matches in the top-flight and made 3.0 tackles and interceptions per match.
Trippier recorded the third-highest and fourth-highest average ratings within the Spurs squad in those seasons respectively and this shows that he was one of the club’s top performers during that period of time.
He was then sold to LaLiga giants Atletico Madrid for a fee in the region of £20m in the summer of 2019 and this meant that Levy raked in a profit of roughly 471% on the initial £3.5m outlay to bring him to North London from Burnley back in 2015.
Tottenham enjoyed two fantastic years of service, along with another two as a squad option before his final years, from the England international and then made an enormous profit on him to conclude his time at White Hart Lane.
From a footballing and financial point of view, it was a terrific deal from start to finish and one that Levy can look back on as a success.