Biggest transfer flops of all time: Coutinho contributes to £774m down the drain

While there have been plenty of transfer bargains in football, there has also been an eye-watering amount of money wasted on players that were simply not good enough for their clubs.

Here, FootballWhispers picks out the biggest transfer flops of all time by position.

4-2-3-1
Transfer fees at time of signing Football Whispers
Striker
Joao Felix, Atletico Madrid, £109m
Left winger
Jadon Sancho, Manchester United, £73m
Attacking midfielder
Philippe Coutinho, Barcelona, £116m
Right winger
Antony, Manchester United, £81m
Central midfielder
Paul Pogba, Manchester United, £90m
Central midfielder
Arthur Melo, Juventus, £69m
Left-back
Milos Kerkez, Liverpool, £40m
Centre-back
Nathan Kilman, West Ham, £41m
Centre-back
Axel Disasi, Chelsea, £39m
Right-back
Aaron Wan-Bissaka, Manchester United, £47m
Goalkeeper
Kepa Arrizabalaga, Chelsea, £69m

*all fees from Transfermarkt

GK: Kepa Arrizabalaga

Featured in our article of Chelsea’s worst Premier League signings of all time, Kepa Arrizabalaga remains the world's most expensive goalkeeper despite Chelsea signing him in 2018.

He made numerous mistakes in his first couple of seasons with the Blues, and was quickly dropped as their number one before being loaned out to Real Madrid and Bournemouth, and eventually sold for as little as £5m to Arsenal.

RB: Aaron Wan-Bissaka

Aaron Wan-Bissaka was not actually awful at Manchester United, but he did cost a lot of money.

He failed to win the Premier League or Champions League at Old Trafford, and was sold to West Ham United for over a £30m loss.

RCB: Axel Disasi

After his first season with Chelsea, it quickly became apparent that they did not fancy Axel Disasi.

Spending a hefty £39m for him, he has recently been sent out on his third loan spell away from the club to Crystal Palace.

LCB: Max Kilman

Max Kilman is still playing for West Ham, despite being relegated from the Premier League last season.

He has never been rated by a large portion of Hammers fans, and never looked close to the £41m they paid Wolverhampton Wanderers to sign him.

LB: Milos Kerkez

Milos Kerkez of Liverpool – Photo by Alfie Cosgrove / News Images / Sipa USA / Icon Sport

Perhaps a harsh pick as he has only had one full season at Liverpool, but Milos Kerkez has not performed to the level he was doing at Bournemouth.

The left-back struggles to defend, evident by being unable to track Anthony Elanga back after he scored the opener in Liverpool's 2-2 draw at Newcastle United in their first game of the new season, and has not offered enough going forward either.

RCM: Arthur Melo

Another player who flopped at Liverpool was Arthur Melo, although he is perhaps most remembered for Juventus splashing £69m on him in 2020.

The fee was especially significant as it was in the year that Covid spread, and he was incidentally released by Juve this summer after four loan spells away from the club.

LCM: Paul Pogba

Paul Pogba had two spells at Man United, but after being released as a youngster, the Red Devils brought him back for £90m.

Unfortunately, Pogba never lived up to the hype he had at Juventus after winning World Cup 2018 with France, and he was released again by the club, resulting in a £90m loss!

CAM: Phillipe Coutinho

Phillipe Coutinho is the most expensive flop in this XI at £116m, the fee Barcelona paid to sign him from Liverpool.

It was just not meant to be at the Camp Nou, where the Brazilian managed an underwhelming 39 goal contributions in 106 appearances before being loaned out twice to Bayern Munich and Aston Villa and sold to the latter.

RW: Antony

antony
Antony is one of Man United's worst-ever players – Photo by PA Images / Icon Sport

Headlining our article of Man United’s worst Premier League XI of all time, Antony was signed for a hugely inflated fee.

He struggled for any consistent output at Old Trafford, recording just 17 goal contributions in 96 appearances.

ST: Joao Felix

Joao Felix is the second-most expensive player in this XI, signed by Atletico Madrid for £109m.

For that sum of money, they would have expected so much more than what the Portuguese delivered, who never hit double figures for goals in LaLiga.

LW: Jadon Sancho

The fourth Red Devils player in this XI and judged by us as Man United's worst Premier League signing of all time, Jadon Sancho completes our team of flops.

Like many of Man United's other signings, there was a lot of hype when Sancho arrived at Old Trafford, but he managed just 18 goal contributions in 83 appearances and was released by the club this summer.


Adam is a lead writer on Football Whispers. He is a big Arsenal fan, and also follows his local club Wealdstone, made famous by The Wealdstone Raider, who he has interviewed. Adam also follows darts, boxing, cricket and tennis, among many other sports.