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5 Players Tottenham Hotspur Shouldn't Have Let Go in the Premier League Era

Sam RookeJun 24, 2016

Buying players is never a sure thing, and every club has signings they wish they could take back. 

The same can be true of players moving the other way.

A simple fact of life for every football club not called Real Madrid is there is always a bigger fish. 

Players are inevitably drawn upward, and while Tottenham Hotspur generally benefit from this force, they are also occasionally victimised by the truly elite clubs. 

Players such as Dimitar Berbatov, Luka Modric and Gareth Bale have been begrudgingly allowed to leave in recent years, so those players do not find a place on this list. 

Pat Jennings provides the archetype of a player Spurs should not have sold. 

The legendary goalkeeper was allowed to join Arsenal after 13 years and 472 league appearances for Tottenham and went on to play eight further seasons at Highbury. 

He is perhaps the only player universally popular among both Spurs and Arsenal fans, which is no mean feat.

This list is confined, though, to the Premier League era.

Teddy Sheringham

1 of 4

Teddy Sheringham is a player who has the strange honour of twice leaving Tottenham. 

His first departure, to Manchester United in 1997, is not included on this list. 

Spurs were reluctant sellers in that case, but Sheringham forced through the move and went on to win numerous trophies with United, including the Premier League, FA Cup and Champions League.

He returned to Tottenham after four seasons and hit 13 goals in each of the next two campaigns. 

Sheringham was 37 and apparently beyond his best, so manager Glenn Hoddle made the decision to release him. 

He joined Portsmouth in 2003 and led them to a 13th-place finish, ahead of Spurs on goal difference. 

Forty goals, for both Pompey and then West Ham United, followed before he moved to Colchester United at the age of 41. 

In the years after his departure, Robbie Keane and Jermain Defoe emerged as the club's main strikers. 

How that energetic duo could have benefited from his nous and experience.

Stephen Carr

2 of 4

Stephen Carr was twice named in the PFA Premier League Team of the Year at Tottenham and bridged the gap between Sol Campbell and Ledley King as club captain. 

An excellent servant and a reliable full-back for the better part of a decade, Carr's move to Newcastle United in 2004 left a hole in Spurs' back line that went unfilled until Kyle Walker's emergence five years later.

Carr was plagued by a knee injury but was still able to play regularly after moving to St James' Park and retired nine years after leaving Spurs. 

He was warmly welcomed when he returned to White Hart Lane with both Newcastle and Birmingham City, but Spurs would have been better off if Carr had remained at the club.

Mounir El Hamdaoui and Frederic Kanoute

3 of 4

The departures of both Carr and Sheringham could have been judged as bad moves at the time, but some sales only look bad in hindsight. 

Mounir El Hamdaoui and Frederic Kanoute's fall into that category. 

At Spurs, Kanoute was often stuck behind Keane and Defoe or shoehorned into an ungainly three-man forward line. 

He struggled to express himself in his two seasons at Tottenham but went on to great success after joining Sevilla in 2005.

He struck 137 goals in seven seasons as he became one of Spain's most feared strikers. 

So successful was he that Spurs were routinely linked with big-money moves to bring him back to England. 

El Hamdaoui's story was similar. 

After failing to make an appearance in one-and-a-half seasons at White Hart Lane, the Moroccan striker returned to the Eredivisie and quickly recovered his scoring touch. 

Spurs were breaking into England's elite in the late 2000s while El Hamdaoui was lighting up Dutch football.

They could have certainly found use for his talents.

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David Ginola

4 of 4

David Ginola is among the most beloved Tottenham players of the last several decades. 

The French wing wizard was a rare source of joy for Spurs fans in the club's darkest period since relegation in the 1970s. 

Between 1996 and 2005, Tottenham finished in the top half of the Premier League once. 

It was an abject period, and Ginola's brilliance shone through the gloom.

He was the lone throwback to the club's glory days, and his sale by George Graham was unforgivable. 

Ginola was 33 at the time of his move to Aston Villa in 2000, but his output mattered in a team producing little of value beyond his joyful touches. 

Perhaps retaining Ginola wouldn't have carried the club forward, but given that seven more seasons would pass before the club won another trophy after his departure, it is evident his sale didn't help. 

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