Football FanCast has taken a look at some of Tottenham Hotspur’s worst transfers under chairman Daniel Levy in N17.

There have been a number of disasters in the transfer market under the chairman’s tenure, with millions wasted on underwhelming players as Spurs have struggled to invest wisely, time after time.

But who are the club’s worst signings? We’ve listed 10 signings Levy and the Spurs supporters would rather forget about…

10 Vlad Chiriches (£8.5m)

Romanian defender Vlad Chiriches was one of the seven players Tottenham signed in the summer of 2013 using the world record fee that had received for Gareth Bale from Real Madrid, and it would be fair to describe the majority of the signings as flops – Chiriches amongst them.

The centre-back was signed for the relatively modest fee of £8.5m from Steaua Bucharest and even had a reasonable start to life at White Hart Lane, starting 13 of the first 25 league games, but following a back injury part way through the season, he began to be frequently left out of the squad altogether.

In total, Chiriches would make just 43 appearances for the Lilywhites during his two-year stint with the side, after which he was sold to Napoli, where he would again struggle to nail down a place in the team.

9 Paulinho (£17m)

Paulinho has such a strange footballing career path behind him – a career path that includes two terrible years at White Hart Lane in the mid-2010s.

There was a lot of excitement when Spurs signed the Brazilian midfielder from Corinthians in July 2013 for a fee somewhere in the region of £17m. He had been tearing it up back home in Brazil and was generally viewed as one of the country’s next great exports when he put pen to paper to join the Lilywhites.

Unfortunately, for whatever reason, he was simply unable to replicate the form he had shown back home in the Premier League, and after two underwhelming years, he opted to join the then-burgeoning Chinese Super League.

Despite his failure at Tottenham, he has enjoyed some serious success in a top-five league after spending two seasons on loan with La Liga giants Barcelona between 2017 and 2019, helping them win the title in the 2017/18 season.

8 Jack Clarke (£9.4m)

Although not the most costly, Jack Clarke’s transfer from Leeds United to Spurs in 2019 was quite bizarre.

Clarke was a dazzling winger during Marcelo Bielsa’s reign at Leeds, and his performances earned him a move to the Premier League at the age of 18.

However, he was loaned straight back to the West Yorkshire club before returning in January, midway through Leeds’ Championship-winning campaign.

A series of loans to QPR, Stoke City and Sunderland followed, before the latter club signed Clarke on a permanent deal for an unknown fee.

Now, after making just four appearances during his Spurs career, the 22-year-old is ripping it up in the Championship with the Black Cats, and joined the second-tier side on a permanent deal in the summer of 2022.

The Englishman scored nine league goals this past season whilst providing 12 assists and was the joint-top assister in the whole division alongside Coventry forward Viktor Gyökeres.

He has also started the current campaign in fine fettle, with Clarke the joint-top goalscorer in the Championship at the time of writing, along with having one of the best conversion rates in the division.

7 Clinton N'Jie (£12m)

In the aftermath of selling Roberto Soldado to Villarreal after his terrible spell with the club and Emmanuel Adebayor not being given a squad number, Tottenham desperately needed another striker to provide cover to an increasingly important Harry Kane. Step forward, Clinton N’Jie.

The 22-year-old had just come off an impressive season with Ligue 1 side Lyon, in which he scored eight goals and provided nine assists, and so Spurs spent the £12m necessary to sign the young striker.

The expectation on N’Jie’s shoulders wasn’t huge. He was there to play second fiddle to Kane, to come off the bench and to play in some of the less important games, and yet, to say he underdelivered would be a colossal understatement.

Across his one and only season in north London, he played in 14 games, scored zero goals and provided just one assist, which surprisingly came against Manchester City, of all teams.

After his thoroughly disappointing season with the club, he was sent on loan to Marseille for the 2016/17 campaign, eventually signing for the French side a year later.

6 Vincent Janssen (£18.9m)

In search of a reliable and prolific backup for the emerging Harry Kane, Tottenham signed Vincent Janssen from AZ Alkmaar in July 2016.

Off the back of 27 Eredivisie goals in the prior campaign, expectations for the Dutchman were rather high, however, after scoring two league goals during his first season in English football, Tottenham decided to loan their expensive striker to Turkish side Fenerbahce.

Four Süper Lig goals and an injury-stricken 2018/19 Premier League campaign saw Janssen finding himself leaving north London on a permanent deal in July 2019, signing for Liga MX side Monterrey, ending a pretty dull spell in England,

5 David Bentley (£15m)

It’s hard to imagine it now, but back in 2008, there was a lot of hope and excitement around David Bentley that he could be the next David Beckham – or at least, that’s what Spurs were expecting when they spent £15m to sign him from Blackburn Rovers at the time.

Now, £15m might not seem like a lot in the era of football we’re living in, but in 2008, that still represented a hefty investment from the club, and unfortunately, this was an investment that went poorly.

In all, the former Hale End graduate would make just 62 appearances for the club, scoring five goals and providing 11 assists, which wasn’t enough to justify keeping him at the club.

Whilst still a Spurs player, he would spend time on loan at Birmingham City, West Ham United, FC Rostov and Blackburn Rovers before eventually calling time on his career in 2014 after spending a year away from the game.

4 Matt Doherty (£14.7m)

Matt Doherty was signed by Jose Mourinho in the summer of 2020 for £14.7m, which seemed to be a reasonable price for a Premier League-proven player, but the fact that he worked best as a wing-back despite Mourinho not using them only signalled how his time in N17 was going to go.

He didn’t play much under the Portuguese manager, nor did he play much under his former boss at Wolves, Nuno Espirito Santo, or Antonio Conte when they took charge.

In all, the former Wolves man made just 44 Premier League appearances for the club during his three-year stint.

He joined La Liga outfit Atletico Madrid in January 2023, but after making just two appearances in all competitions, he opted to re-join Wolverhampton Wanderers in the summer.

It was a deal that looked great on paper, but things just never worked out for the Irishman in north London.

3 Giovani Lo Celso (£41.1m)

Giovani Lo Celso initially joined Spurs in 2019 on a season-long loan, but the club were required to pay a loan fee worth £13.7m.

After the completion of a rather underwhelming loan spell, Tottenham forked out a further £27.4m to sign the Argentinian on a permanent deal.

Lo Celso made 84 appearances in total, scoring eight goals, and subsequently got shipped out on two seperate loan deals to Villarreal.

At the time of his move to Spurs, the 42-cap international had a market value of €50m (£42.9m) according to Transfermarkt, but now, almost four years on, his value has been slashed to €14m (£12.1m), despite being in his prime years.

Despite not yet shining in Spurs colours, Lo Celso remains with the club and could yet have the chance to rewrite his career at Tottenham under Postecoglou.

2 Roberto Soldado (£26m)

Roberto Soldado joined the club in 2013 during the relatively short reign of head coach Andre Villas-Boas from La Liga outfit Valencia for what was then a club-record fee.

In the previous season leading up to his mega move, Soldado netted a whopping 30 times – a tally that included four Champions League goals.

However, for whatever reason, his prolific output in front of goal failed to translate to the Premier League, with the Spain international managing just six league goals.

In his final year at Spurs during the 2014/15 campaign, Soldado struck just one league goal and ultimately left the club that summer to return to Spain with Villarreal.

1 Tanguy Ndombele (£53.8m)

Spurs signed Tanguy Ndombele from Ligue 1 side Olympique Lyon for a club-record fee in the summer of 2019.

At the time of the move, Ndombele was a young, up-and-coming 22-year-old midfielder, seemingly with the world at his feet. Tipped for big things, the Frenchman failed to deliver and subsequently found himself on the bench for much of his Spurs career.

Now, after two loan spells away from the north London club, the 26-year-old is set to return for pre-season training after winning Serie A with Napoli.

Maybe he’ll finally repay his substantial price tag by resurrecting his career under Postecoglou, but that doesn’t seem likely at present, with the Frenchman being sent on loan to Galatasaray for the season.