#3 Nicolas Pepe to Arsenal - €80 million
Nicolas Pepe was Arsenal's marquee signing of the 2019 summer transfer window. He was brilliant for Lille in the 2018-19 season, scoring 23 goals and providing 12 assists in 31 appearances across all competitions. But even then paying €80 million for a mercurial winger seemed a bit much.
Arsenal still decided to go for it. They made Pepe their most expensive signing by a country mile. Their second-most expensive signing is Pierre-Emerick Aubameyang who was signed for €63.75 million.
Pepe is yet to justify his price tag after two seasons at Arsenal. He scored just eight goals and provided 10 assists in 42 appearances across all competitions in his debut season in the Premier League.
Pepe did better in the 2020-21 season, scoring 16 goals and providing five assists in 47 appearances. But that's not the kind of returns Arsenal would expect from a player they've spent €80 million on.
#2 Andy Carroll to Liverpool - €41 million
Liverpool are no strangers to the hype train either. €41 million was quite a big sum in 2011. But Liverpool were ready to shell out big money in order to sign Carroll. The Merseysiders were looking to replace Fernando Torres and that was not going to be an easy task. Spending €41 million on Andy Carroll only made it tougher.
They signed him in January 2011 making him the second most expensive footballer to play for a British club, after Torres. He also became the most expensive British signing at the time.
Carroll scored just two goals for Liverpool from January up until the end of the 2010-11 season. In his first full season with Liverpool, Carroll scored nine goals and provided six assists from 47 appearances.
He did produce a few match-winning performances for Liverpool in the 2011-12 season. However, his haul of seven goals and four assists from 26 appearances across all competitions wasn't enough for the Merseysiders to retain him.
He was subsequently sent out on loan to West Ham United for the 2012-13 season. West Ham United then signed him on a permanent basis in 2013 for a sum in the ballpark of €18 million.
#1 Kepa Arrizabalaga to Chelsea - €80 million
With Thibaut Courtois securing his dream move to Real Madrid, Chelsea had to find a player who could match the Belgian's heroics between the sticks. They were ready to spend big and shelled out €80 million to sign Kepa Arizzabalaga from Athletic Bilbao.
What Chelsea got instead was a young, nervy goalkeeper with an attitude problem. Once tipped to replace David de Gea as the Spain's no.1, he is currently playing second fiddle to Edouard Mendy at Chelsea.
A slew of grave goalkeeping errors and a public on-the-field fallout with then manager Maurizio Sarri distanced him from the Chelsea fanbase. It remains to be seen if Arizzabalaga will be able to revive his Chelsea career. But for now, he is their biggest transfer flop.