Tottenham’s current squad possesses a large number of desirable players.
The likes of Harry Kane, Christian Eriksen and Toby Alderweireld have all been linked with moves up the footballing ladder while Jan Vertonghen and and Dele Alli would start for most of the Premier League’s top clubs.
If they qualify for the Champions League this season, Spurs will be confident of keeping their best players – bar a couple of potential departures – and continuing their quest for silverware.
In the past, however, talented individuals have made their names at White Hart Lane only to push to be allowed to leave when a bigger offer came in. But how did those names perform when they finally got their move?
Joined: Manchester United (£3.5m)
Appearances for new club: 145 (46)
Notable achievements: Premier League x 3, Champions League, FA Cup, Intercontinental Cup, Charity Shield
Sheringham is regarded as a Manchester United legend having joined the club as a 31-year-old, scoring the crucial equaliser in the famous Champions League win of 1999.
It wasn’t always happy times for the striker at Old Trafford with playing time limited in his first couple of seasons at the club but Sheringham did the job he was brought in to do and won three league titles in four years, before returning to Spurs.
Joined: Arsenal (free transfer)
Appearances for new club: 211 (12 goals)
Notable achievements: Premier League x 2, FA Cup x 3, Community Shield
The original “Judas”, Campbell shocked north London and the whole of the Premier League when he departed Spurs to sign for rivals Arsenal in 2001 but, looking back, the move was a highly successful one.
Campbell established himself as a crucial member of Arsenal’s defensive line for both of their title winning seasons before departing the club after five successful years. His final appearance of his first, main stay with the club was the Champions League final.
Joined: Manchester United (£18.6m)
Appearances for new club: 459 (24 goals)
Notable achievements: Premier League x 5, Champions League, FA Cup, Europa League, Football League Cup x 2, Community Shield x 6, FIFA Club World Cup
Carrick rejected the offer of a new contract at Tottenham to move to Manchester United and, over ten years later, the midfielder is still an integral part of the Red Devils’ set-up.
After 16 trophies across a decade of regular first-team football, Carrick was a key player for the Manchester club before retiring and joining Jose Mourinho’s coaching staff. He has continued that role under new manager Ole Gunnar Solskjaer.
Joined: Portsmouth (£6m)
Appearances for new club: 36 (17 goals)
Notable achievements: None
Jermain Defoe was allowed to leave Spurs in January 2008 after a struggle to earn a regular starting place, with the England international joining Portsmouth.
Defoe ended up only spending 12 months on the south coast but what a prolific time it was for the striker. It was so good that Spurs re-signed him, for significantly more money, just a year later having scored 17 goals in 36 games.
Daniel Levy would state when Defoe was brought back that the club had been keen to keep the striker. He had even been offered a new deal prior to his initial exit, but the forward sought a move for regular action.
He found it and played extremely well.
Joined: Liverpool (£19m)
Appearances for new club: 28 (7 goals)
Notable achievements: None
Robbie Keane’s time at Liverpool is a strange period in the striker’s career. A move was made in the summer of 2008 and it took a while for the Irishman to find his feet, but seven goals in all competitions from 28 games wasn’t a terrible return despite some goalscoring troubles in the league.
Rafa Benitez, however, decided to accept an offer of £12m from Spurs to sign him back just six months later, ending Keane’s short spell on Merseyside. Perhaps if Keane had stayed at Liverpool longer he could have enjoyed much success, but such a stint can only be looked at as a failure.
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Joined: Manchester United (£30.75m)
Appearances for new club: 149 (56 goals)
Notable achievements: Premier League x 2, Football League Cup, Community Shield x 2, FIFA Club World Cup
Transfer deadline day in 2008 was perhaps one of the most manic ever as Berbatov, despite reportedly being told to go to Manchester City, pushed through a late move to rivals United.
For a while it looked like the Bulgarian was a waste of money as Berbatov struggled for form but after a difficult first 18 months at Old Trafford he found his feet. The striker’s time is looked upon fondly as he netted some crucial goals, was named in the PFA Team of the Year for 2010-2011 and also got a hat-trick against Liverpool.
Joined: Liverpool (free transfer)
Appearances for new club: 20
Notable achievements: None
The most recent name on this list, Stewart left Spurs to join boyhood club Liverpool in 2014 and the 23-year-old midfielder impressed at youth level before making his competitive debut in January 2016.
However, the summer of 2017 saw him make the move to Hull City.
Having played so few games at Liverpool before his Hull move, it is harsh to judge this move one way or the other. But given Mauricio Pochettino’s knack for developing and playing youngsters there’s a possibility that remaining in north London could have been more beneficial for Stewart’s career.
Joined: Manchester City (£50m)
Appearances for new club: 89
Notable achievements: Premier League, Football League Cup x 2
Kyle Walker was one of Manchester City’s marquee signings in the summer of 2017, joining for a cool £50m. He went straight into a side that eventually won the Premier League for the second time in their history with Walker playing a major role in that success.
Walker took a while to break into the Spurs first team having to go out on loan three times before making the right back position his own. The last of those loans, to Aston Villa, saw him start to show the promise that Tottenham has signed him for back in 2009 when they paid Sheffield United £9m for both Walker and Kyle Naughton.
But such is the way of many a Tottenham player, just as he got great he left to. The chance of immediate success was just too much for him to turn down it would seem.