Despite failing to win the English top-flight since 1961, Tottenham remain one of the country’s traditional “big clubs” and the chance to play for them has been difficult to turn down for many footballers over the years.
A vast array of players have enjoyed impressive careers with Spurs, but there are also those who have joined the Londoners only begin a gradual journey downhill.
From established strikers who suddenly can’t score to once-promising young stars who fail to live up to their billing, Tottenham have had their fair share of disappointments. Here are 14 of the most notable examples.
1. David Bentley
Appearances for Spurs: 62
Clubs played for since: Birmingham (loan), West Ham (loan), FC Rostov (loan), Blackburn (loan)
In the summer of 2008, David Bentley made the next major step of his career by leaving Blackburn Rovers for Tottenham, where Juande Ramos’ side looked ready to build on their League Cup success of the previous season.
Things didn’t work out, however, and Ramos was gone after just eight games and no wins. Bentley had failed to replicate his Blackburn form until new manager Harry Redknapp’s second game in charge against Arsenal at the Emirates.
Bentley scored a stunning goal against the club he left as a youngster, and many believed he would kick on in a Spurs shirt from there. Unfortunately, that didn’t happen.
Once dubbed the next David Beckham, Bentley ended up playing a bit-part role for Tottenham before leaving on a series of loans. He eventually retired in June 2014 at the age of just 29, telling Sky Sports: “I’ve fallen out of love with the game.”
2. Roberto Soldado
Appearances for Spurs: 76
Clubs played for since: Villarreal, Fenerbahce
Of the seven players who Spurs bought with the money garnered from the sale of Gareth Bale to Real Madrid, only two – Christian Eriksen and Erik Lamela – are still in north London. Even more so than Paulinho, who somehow eventually found himself at Barcelona, Roberto Soldado was the biggest flop of the ‘Magnificent Seven’.
Brought in to be the main replacement for Bale’s goals, Soldado scored just 16 times over two seasons with Tottenham, including six strikes in the Premier League. His below-par performances forced Spurs to turn to young striker Harry Kane, so things did eventually work out quite well for the club.
The same can’t be said for Soldado, who has struggled for goals at both Villarreal and Fenerbahce since leaving England. He scored nine goals in the Super Lig last season, a far cry from his tally of 24 La Liga strikes during his final campaign at Valencia.
3. Vincent Janssen
Appearances for Spurs: 36
Clubs played for since: Fenerbahce (loan)
Having finally found a lethal frontman in the shape of Kane, Tottenham sought a striker who could offer both cover and competition for their talisman ahead of the 2016/17 season.
In came Vincent Janssen from AZ Alkmaar, the young Dutchman who had scored 27 goals in 34 Eredivisie appearances the season prior, breaking into the Netherlands national team in the process.
But Janssen failed to convince either Mauricio Pochettino or the Spurs supporters he was worth a place in the starting line-up. He also struggled to provide adequate back-up for Kane, who continued to make most other strikers average.
It’s fair to say Janssen truly was average, though, scoring only two Premier League goals and being shipped off on loan to Fenerbahce after one miserable season in England. Now back at Tottenham, deemed surplus to requirements and having recently undergone foot surgery, his future is up in the air.
4. Lewis Holtby
Appearances for Spurs: 42
Clubs played for since: Fulham (loan), Hamburg
Midway through the 2012/13 season, Spurs agreed to sign Schalke 04 midfielder Lewis Holtby on a free transfer the following summer. But the club jumped at the chance to bring the deal forward to January, paying £1.25m to do so, according to the Guardian.
Highly rated from his time in Germany, Holtby impressed just enough during his first few months in England – despite failing to score – to ensure Tottenham had completed a shrewd piece of business.
It soon became clear that the youngster didn’t possess the sufficient quality to make it at Spurs and he was loaned to Fulham – where he was relegated with the Cottagers – after just a year at White Hart Lane.
Another loan to Hamburg followed, and the Bundesliga club eventually took him back to Germany permanently. Now playing in the German second tier, Holtby has done little to suggest he can resurrect his once promising career.
5. Steven Pienaar
Appearances for Spurs: 18
Clubs played for since: Everton, Sunderland, Bidvest Wits
In January 2011, Steven Pienaar had to choose between Tottenham and Chelsea for his next club after an impressive three-and-a-half years with Everton.
Upon joining Spurs, the South African claimed he chose Redknapp’s side because of their “ambition” and style of play. Sadly for Pienaar, he didn’t get to experience Tottenham’s style very often.
Perhaps it was because he played in the same position as Gareth Bale, but Pienaar never really found his feet in north London. A loan return to Goodison came about the following January, which soon became permanent.
And despite initially winning his place back in the Toffees’ line-up, the winger soon began to fall out of favour and his game time reduced, playing just six times in 2015/16 before being sold to Sunderland. Now retired after a short spell back in South Africa, Pienaar may still regret joining Spurs in the first place.
6. Sergei Rebrov
Appearances for Spurs: 75
Clubs played for since: Fenerbahce (loan), West Ham, Dynamo Kiev, Rubin Kazan
For a certain generation of Tottenham fans, Sergei Rebrov is the archetypal big-money flop who preceded a number of similar strikers, some of whom are mentioned in this article.
Rebrov remains the all-time highest scorer in the Ukrainian Premier League with 123 goals in 261 games, but he lost his scoring touch at Spurs, finding the net just 15 times between 2000 and 2002.
Later spells with Fenerbahce, West Ham and Rubin Kazan were equally disappointing, although he scored a few more goals with former club Dynamo Kiev before retiring.
7. Kevin Wimmer
Appearances for Spurs: 31
Clubs played for since: Stoke City, Hannover
Brought in as cover at centre-back in the summer of 2015, Wimmer impressed when called upon to stand in for the injured Jan Vertonghen for a couple of months in 2015/16.
It seemed Tottenham had bought wisely until the Austrian fell out of favour and was barely used the following season, making just 10 appearances in all competitions.
Wimmer joined Stoke City on loan for the 2017/18 campaign but struggled to cement a place in the team and was subsequently sent to train with the Under-23s because of a lack of fitness, according to the Telegraph.
He is now on loan at Hannover in Germany, having failed to capitalise on his big break at Spurs.
8. Giovanni dos Santos
Appearances for Spurs: 33
Clubs played for since: Ipswich (loan), Galatasaray (loan), Racing Santander (loan), Mallorca, Villarreal, LA Galaxy
Yet another player once tipped to achieve great things, Giovanni dos Santos filled Tottenham fans with excitement by scoring a hat-trick in his final appearance for Barcelona before moving to White Hart Lane.
But the Mexican endured a torrid time at Spurs, playing just 33 times over four years with Redknapp unwilling to give him an extended run of games.
“If he could pass a nightclub as well as he can pass a ball he would be alright,” said Redknapp at the time, as quoted by the Mail. Little changed and Dos Santos was soon sold permanently after a few loans.
The Mexican has somewhat resurrected his career with modest success on the international stage and with LA Galaxy. But there is a lingering sense of what-could-have-been for the talented winger.
9. Emmanuel Adebayor
Appearances for Spurs: 113
Clubs played for since: Crystal Palace, Istanbul Basaksehir
This is a bit of a strange one because Emmanuel Adebayor actually experienced a year-long upswing in fortunes when he arrived at Tottenham on loan from Manchester City in August 2011.
His City career had petered out badly, and he wasn’t hugely convincing during a loan spell with Real Madrid – despite scoring twice in a Champions League quarter-final against Spurs.
But Redknapp’s gamble paid off. Adebayor scored 17 goals in 33 Premier League appearances in 2011/12, which was enough to tempt Tottenham into buying him permanently.
However, his numbers and application soon began to dwindle. It took until the summer of 2015 for him to leave after a final two-goal campaign. And although he has done reasonably well in Turkey, the former Arsenal striker no longer holds his underrated status of old.
10. Sebastian Bassong
Appearances for Spurs: 71
Clubs played for since: Wolves (loan), Watford, Norwich
A debut goal against Liverpool on the opening day of the 2009/10 season made it look as if Spurs had made the right choice by luring Sebastian Bassong from Newcastle United.
Alas, it wasn’t long until the centre-back was warming the bench, his defending clearly not up to scratch for a team with Champions League aspirations.
Bassong is currently without a club after leaving Championship side Norwich City at the end of last season. Make of that what you will.
11. Kyle Naughton
Appearances for Spurs: 74
Clubs played for since: Middlesbrough (loan), Leicester (loan), Norwich (loan), Swansea
When Tottenham completed a double swoop for Sheffield United youngsters Kyle Naughton and Kyle Walker, it was the older of the two, Naughton, who was expected to break into the team at right-back.
Part of Naughton’s failings relates to being compared to Walker, who has gone on to achieve huge success with Manchester City since leaving Spurs.
Now a regular for Swansea City, Naughton is back in the division his quality matches: the Championship. He did a decent job filling in at left-back for Tottenham from time to time, but he was never quite good enough to play on his preferred side.
12. Bobby Zamora
Appearances for Spurs: 18
Clubs played for since: West Ham, Fulham, QPR, Brighton
After scoring 83 goals in 136 appearances during his first spell at Brighton, Bobby Zamora earned the first big move of his career to Tottenham.
But in 16 Premier League games for Spurs he failed to score a single goal, managing his only strike for the club in the League Cup before being sold to West Ham United.
Zamora enjoyed decent runs of form with the Hammers and Fulham but never became the player he was expected to turn into at Tottenham.
13. Fernando Llorente
Appearances for Spurs: 31
Clubs played for since: N/A
After Janssen’s failure to provide the necessary level of competition for Kane, Spurs moved for Swansea striker Fernando Llorente, who had scored 15 goals in 33 Premier League appearances in Wales since joining from Juventus.
The Spaniard was expected to add not only a back-up option but the experience Tottenham’s young squad needed to challenge for trophies. Instead, he resembled an inexperienced, sheepish striker low on confidence and unable to give Kane a run for his money.
With just one Premier League goal for Spurs to date, Llorente’s once discreetly flourishing career appears to be on the wane.
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