#5 Ben Chilwell

After Liverpool’s defeat in the Europa League final in 2016, it was clear that the Reds needed a new left-back. Ahead of the 2016/17, Liverpool attempted to sign Leicester City’s Ben Chilwell when he was still a promising player yet to break into the first team.
There are two theories on why a deal for the Foxes full-back collapsed. According to the first one, Liverpool offered to pay £7m including add-ons for Chilwell but Leicester demanded £10m. As was the case with Teixeira, Klopp and co were unsure if the player was worth the asking money.
The second theory is that Liverpool were unwilling to match the player’s demands at that time and this theory is further cemented by the fact that Chilwell signed a new contract at Leicester shortly after the transfer to Liverpool failed.
Klopp opted against signing a left-back that season and played James Milner as Liverpool’s first-choice left-back for the entirety of the season.
Although a transfer for Chilwell failed, what it shows is the brilliance of Liverpool’s scouting department. Chilwell became a key starter for Leicester during the 2017/18 season and he is now England’s first choice left-back.