In almost 25 years as Tottenham Hotspur chairman, to say that Daniel Levy wasn't known for his deep pockets would be an understatement. Unlike those around them, Spurs were often criticised for putting profit at the centre of their ambitions rather than silverware throughout his tenure.
Meanwhile, when Spurs did spend big, it didn't always go to plan. They unlocked financial freedom after selling Gareth Bale in 2012, as Real Madrid secured the Welshman for a staggering £85m fee. But what came next was transfer flop after transfer flop. It could even be argued that they only managed to replace Bale eight years later when they signed the man himself on loan from Real Madrid.
The fact is, from Roberto Soldado to Vincent Janssen as well as many in between, Levy rarely spent well in North London. So much so, that we've now ranked the worst signings that he made during his time at Tottenham.
Whilst Clinton N'Jie is far from the most expensive player on his list, he is one of the most disappointing. The 22-year-old arrived as a player full of potential in 2015, with Mauricio Pochettino at the peak of his powers. He was billed as a player destined for big things and seemed as though Spurs landed the ultimate transfer coup as a result.
In what turned into quite the trend, however, Levy guessed wrong. N'Jie went on to make just 14 appearances for the Lillywhites before leaving for Marseille just two years on from arriving. Failing to score and assisting just one goal in those 14 appearances, it's fair to say that the winger never lived up to the hype.
A more recent inclusion, Yves Bissouma, is the topic of much frustration in North London. The talent is quite clearly there. At his best, he is exactly the midfielder that Tottenham hoped to sign for just £30m in 2022. But ability isn't the issue.
There were many questions about Bissouma's discipline when Ange Postecoglou suspended the midfielder from club duties last season, forcing the former Brighton man to earn back his redemption and those concerns have only increased under Thomas Frank.
A fresh start provided Bissouma with a clean slate that he has already mudded with disciplinary issues. Frank told reporters after leaving him out of his Super Cup squad to face Paris Saint-Germain: "Bissouma isn't here because of disciplinary reasons. He has been late several times, the latest one too many."
There was a brief moment when Bryan Gil was Tottenham's longest-serving player in the summer and that just about sums up Levy's transfer struggles in North London. The Spaniard spent four years at the club despite spending much of that time out on loan and never making his mark under several managers.
Like N'Jie years prior, Gil was signed as a player for the future and has since become a transfer flop. That said, at 24 years old, it could be argued that the Spaniard never truly received a fair chance in North London and he could yet thrive at Girona. From a transfer flop at Spurs, it would only compile the Lillywhites' misery if Gil went on to become the world-beater that they thought they signed four years ago.
Some went as far as to suggest that David Bentley could be the next David Beckham and that's all the convincing that Levy needed. He and Spurs swooped in to welcome the Blackburn Rovers star in a deal worth £15m in 2008. At the time, that was no small price, either. Big things, as a result, were expected.
After five years at the club and just 62 appearances, Bentley retired at Tottenham. From Beckham comparisons, the midfielder became one of the most disappointing transfer flops of the Levy era.
When thinking about Davinson Sanchez, it's hard not to remember the time when İlkay Gündoğan left him flailing to score for Manchester City. That in itself summed up his struggles at Tottenham. It wasn't all bad, of course, but for a £37m player, many expected more.
The central defender thrived at Ajax and showed initial potential in North London, before ultimately failing to replicate the success of Jan Vertonghen or Toby Alderweireld.
Failing to replace star players has been an ongoing trend at Spurs too. They failed to replace Bale many moons ago, failed to replace Vertonghen and Alderweireld, and are yet to really replace the quality of Harry Kane. In a new era without Levy, that must change.
Paulinho is one of the most memorable Tottenham flops. Mostly because he somehow found his way to Barcelona years later. In North London, things simply didn't click for the Brazilian, who arrived for as much as £17m in 2013. One of the incomings that Tottenham welcomed with the Bale money, the midfielder was part of arguably the worst transfer window in Levy's tenure.
In a two-year spell at White Hart Lane, Paulinho made 67 appearances, scored 10 goals and assisted another seven. As impressive as 16 goal involvements may look from midfield, however, those numbers simply papered over the cracks for a player who simply wasn't good enough in the Premier League.
What was Levy thinking here? Giovanni Lo Celso, to his credit, remains a talented player. Alas, what he is not is a player worth £55m. Once again, those in North London were attempting to finally replace a key player - this time Christian Eriksen - and once again, they failed to do so. In 108 appearances, Lo Celso was involved in just 18 goals.
As Xavi Simons could be about to prove, a player worth around £55m simply must do better. But what makes Levy's deal to sign Lo Celso so much worse is that he then sold the Argentine back to Real Betis in 2024 for less than £10m.
In the space of five years, the Tottenham chief handed the Spanish club £55m for their best player, watched him struggle, and then handed him back for a bargain price.
When AZ Alkmaar sold Vincent Janssen to Tottenham in 2016, it was the advice of 'Moneyball' baseball expert Bill Beane which saw the Dutchman's price tag rise to as much as £15m. Unlike Beane's baseball stars, though, Janssen was not the genius signing that many expected. He was the total opposite.
In 46 appearances, the striker managed just six goals and four assists. He remains one of the worst strikers in Spurs' Premier League history and his presence only enhances the reputation of Harry Kane, who bailed Levy out after his transfer mistake.
If Tottenham fans thought Janssen was bad, then it may be best to avoid their verdict on Roberto Soldado. Signed for around £26m, using a large chunk of the Bale money as a result, the forward never quite got going in a Spurs shirt. More than anyone, he summed up Levy's failure to spend well when handed the chance.
If covering distance wasn't a much-needed asset for any central midfielder, then Tanguy Ndombele may well have gone down as one of the best players to have signed during Levy's reign. On a technical level, he was outstanding. He was almost a throwback to Moussa Dembele with just how press resistant he was. Physically, meanwhile, he could hold almost anyone off when he was in the mood.
Alas, that mood rarely appeared and José Mourinho's criticism was never going to help. Some Spurs fans may persist that under a different manager, Ndombele could have thrived. Mourinho was the man in charge, however, and for all his clear talent, the midfielder remains the biggest flop of the Levy era.
