Tottenham Hotspur are set to be on the hunt for a new left-back in the next transfer window. The North London side have been weak in that position all season. Danny Rose looks set to leave the club, Ben Davies has struggled to stay fit whilst Ryan Sessegnon is seen as an attacker for the time being.
One name that has reportedly been put forward as a potential option for Tottenham is Leicester City defender Ben Chilwell.
The Express reported in February that he was being monitored, as Tottenham’s need for a left-back became clear.
It would be an eye-catching signing for Tottenham if they could secure the England international. But they will surely wish they could have lured him away when they first showed interest back in January 2016.
As reported by The Mirror, Arsenal, and Tottenham were set to make a move for the player, after he had impressed on loan at Huddersfield Town and in an FA Cup match with Spurs.

At the time, the talented youngster was reportedly (The Telegraph) on just £800-a-week at the King Power Stadium and his Premier League debut was nearly one year away, coming in December 2016.
Leicester, however, had big plans for the player and even rejected a £3.5 million offer from Arsenal for his services, as reported by The Telegraph.
Back then, it was conceivable that Tottenham could lure Chilwell away. Now, it seems very unlikely.
The Leicester star is England’s number one left-back and the Foxes have outperformed Tottenham this season. As reported by The Sun, Leicester now value Chilwell at £60 million, a fee Tottenham will surely be unlikely to splash out on a left-back.
It seems Tottenham’s best chance to sign Chilwell was back in 2016 and it passed them by.
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