After Mauricio Pochettino revealed that his current 32-man squad will need to be cut down to 25, we look at the seven players who should be the first out of the door at White Hart Lane.
In the five years since he arrived at White Hart Lane from Sheffield United, Naughton has failed to nail down his position.
He has predominantly been used as cover for both the right-back and left-back slots. Being right-footed, it would appear as though he would prefer to operate as a right-back but if Kyle Walker is fit, he will play ahead of Naughton. Furthermore if, as expected, DeAndre Yedlin moves to White Hart Lane, then Naughton will get even less game time.
It's extremely likely that one of either Dawson or Younes Kaboul will be sold this summer but I think that the latter is more valuable to Spurs.
Dawson's main problem is the fact that he is too slow. Former manager Andre Villas-Boas exposed Dawson's lack of athleticism by operating with a high defensive line and even though Pochettino will play slightly deeper, he requires his defenders to not only play with high energy but also to be able to pass the ball effectively. Dawson can do neither.
Even though Kaboul has had his injury problems, back in the 2011/2012 campaign he was one of the best centre-backs in the league along with Ledley King and if he can stay injury free he is a better all-round defender than Dawson.
He was the first of last summer's big money buys and was Tottenham's record signing until the arrival of Roberto Soldado, but despite all of the hype surrounding his transfer, he had a largely disappointing first season in English football.
Although he initially looked dangerous, as the winter months came around and the teams near the bottom were up for the fight, Paulinho was not. Even though he is a box-to-box midfielder, he is not a big enough goal threat. He isn't as defensively solid as Sandro or Moussa Dembele and isn't as creative as the likes of Christian Eriksen or Erik Lamela.
Paulinho didn't show enough fight to force his way back into the team when he was replaced in the first tea picture by Nabil Bentaleb under Tim Sherwood. With Pochettino's determination to give young players a chance, Paulinho should expect to compete with Tom Carroll also.
Paulinho would still command a transfer fee in the region of £15-£20 million pounds so Tottenham should cash in now before his value plummets.
Tottenham have too many holding midfielders with the likes of Sandro, Dembele, Bentaleb and Carroll all operating in that role. It also appears as though Pochettino is intent on bringing Morgan Schneiderlin to White Hart Lane, limiting the amount of game time Capoue would receive.
He featured only 12 times last season in the Premier League, two of those games were the 5-0 against Liverpool and the 5-1 defeat against Manchester City, both at White Hart Lane, even though he did score in the latter.
There's no doubt that Capoue is a solid holding midfielder but if Tottenham want to break into the top four, he is not at the same level as their rivals with the likes of Nemanja Matic, Yaya Toure and Steven Gerrard all more effective.
Chadli has largely struggled since his move. He scored only one league goal in 24 appearances last season and doesn't have the required turn of pace to be a fully effective Premier League winger.
Lamela has had a good pre-season and is expected to play a big role this season which will limit the amount of opportunities Chadli will receive. He could be used as a make weight in a potential deal for Schneiderlin or Depay.
With the arrival of Ben Davies from Swansea, combined with Danny Rose's new contract, Assou-Ekotto will be the third-choice left back. Having spent the majority of his time at White Hart Lane as the undisputed number one, he won't be willing to play third- fiddle. He looks certain to leave the club after eight years of service.
Even though the likes of Ryan Mason and Christian Ceballos will probably leave on loan, another player who should be sold is South African centre-back Khumalo. He has failed to make a single appearance for Tottenham since his arrival three years ago and there won't be many fans outside of White Hart Lane whp know who he is.
He has proved to be a decent acquisition in England's lower leagues, featuring for Reading, Preston North End and Doncaster Rovers. At the age of 27, he should be in the prime of his career and has to leave White Hart Lane in order to fulfil his potential.
Who do you think Tottenham should sell? Are any of the above still good enough to play for Mauricio Pochettino? Let us know in the comments below.
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