Tottenham Hotspur are a club that has lost its way in recent years, in the relentless pursuit of silverware.

Chairman Daniel Levy would even admit his failures whilst striving for such a goal, which led him astray from the progression he was earning. He told a recent fan forum: "I had gone through a period where we'd almost won. With Mauricio we went through some very good times. We didn't quite get there but we came very close and we had a change in strategy. The strategy was 'let's bring in a trophy manager'.

"We did it twice and look you have to learn from your mistakes. They're great managers but maybe not for this club. For what we want, we want to play in a certain way and if that means it has to take a little bit longer to win maybe it's the right thing for us. That's why bringing Ange in was from my point of view the right decision."

Whilst his managerial moves were questionable across that period, so too has his transfer business, naturally seeking to back each of his new appointments in an effort to push them on towards that trophy-winning goal.

Although there have been some truly terrible acquisitions before Mauricio Pochettino joined the club, many of the more financially draining ones have come following the heavy modern-day injection of ridiculous fees. As such, they likely would litter a list consisting of their worst-ever buys.

Who is Spurs' worst-ever signing?

Whilst many might rush to laud Tanguy Ndombele as easily their most torrid deal, given he still remains their record signing at £63m and is currently out on his third loan since joining in 2019, there are others who might rival the underperforming Frenchman.

For example, if the £60m Richarlison is to continue his barren run in front of goal – having scored just five times to for the club to date – there is every chance he could end up leaving a similarly torrid legacy in north London.

Then, whilst not quite as lucrative gaffes, the likes of Davinson Sanchez, Roberto Soldado and Sergio Reguilon have also drained the club respectively whilst failing to live up to the billing of their initial purchases.

Another who falls into this category is Moussa Sissoko, who joined from Newcastle United as a dynamic right midfielder set to perfectly facilitate Pochettino's full-back-dependant system.

Having impressed on Tyneside, despite his 31 goal contributions across 133 games marking a hardly outstanding return, there was hope he might provide an injection of physicality both out wide and in the engine room alongside some much-needed goals.

However, the latter was definitely in short supply, as he would then score just five times, assisting a further 16 before his eventual departure. In fact, pundit and former Celtic man Chris Sutton would lambast their business, speaking harshly about the 71-cap dud: "Sissoko was a bad buy. And Pochettino's questioning him now.

1

Tanguy Ndombele (Lyon)

£63m

2

Richarlison (Everton)

£60m

3

Brennan Johnson (Nottingham Forest)

£47.5m

"That was a really odd move I think to virtually everybody in the country looking from the outside thinking why on earth have they signed Sissoko? He downed tools last season. How can you trust him? That's a massive disappointment. A lot of money wasted."

Then, the nadir of his Lilywhites career inarguably came in the Champions League final, when his thoughtless decision to physically instruct his teammates saw him concede a penalty within two minutes. Pointing as he stood facing Sadio Mane, a right-footed delivery struck his outstretched arm, and Mohamed Salah would give Liverpool the lead in the biggest game in the north London outfit's history.

Although his actual fee does not amount to even half of Ndombele's, the significant underperformance combined with his equally expensive wages suggests that, pound for pound, the 34-year-old is certainly within the conversation for worst-ever Spurs signings.

How much did Spurs sign Moussa Sissoko for?

Whilst Sissoko's contribution was not completely useless, it was the fee attached to his name that held such huge expectations and therefore made him such a poor signing.

Having already made himself a mini hero before joining, as he reportedly turned his phone off to snub a move to Everton, it quickly became the Toffees who arguably benefitted from that move, having avoided spending £30m on such a disappointment.

He would explain his reasoning behind such a move in 2016: "It’s simple. I spoke with Everton in the past, but they didn’t make an offer to Newcastle when I wanted. And then Tottenham came. And so when they came, I wanted to join this club directly. Because, like I said, it’s a big club. So in my head, everything was clear. I wanted to sign here, that’s why I came here."

How much did Moussa Sissoko earn?

To make matters worse, the current FC Nantes midfielder was handed an equally lucrative deal that truly stretched the Lilywhites' finances.

He would earn a ludicrous £80k-per-week across his five years in north London, which amassed another £20.8m too on top of his initial transfer fee. Therefore, overall Sissoko would drain the club of £50.8m.

Given he was signed with the intention of finding the net with regularity as well as injecting energy, his tally of five meant that Pochettino actually paid £10m for every goal scored.

What is Moussa Sissoko's market value now?

Having enjoyed a brief stint with Watford following the conclusion of his contract, it would quickly become a short stay as the Hornets fell to relegation. As his stock plummeted, he would seek some kind of late renaissance with a return to his homeland, where he now features for FC Nantes.

However, time has not been kind to the 6 foot 2 enforcer, whom Transfermarkt now values at a lowly €2.5m (£2.1m).

It is a testament to their vast overpayment that, according to the website in question, the peak of his valuation came during 2019 and only reached €25m (£21.6m).

Why is Moussa Sissoko worth that much?

The reasoning behind such a low valuation is easy to outline, given his declining powers alongside his increasing age.

Sissoko is reaching the twilight years of an admittedly very solid career, and whilst hardly laden with silverware, he can look back on some key moments with fondness.

However, of late he has even been struggling to shine in Ligue 1, with his 6.45 average match rating simply showcasing that he has shown little to merit any kind of higher value.