The worst signings in Premier League history

Profile Picture: Josh Powell

March 11th, 2021

Some Premier League signings can be fairytale stories. Jamie Vardy, for instance, came from non-league football to Leicester City, and proceeded to break a litany of goalscoring records and guide the club to the most unlikely league title of all-time. Others are big money-moves that pay off for the game’s richest clubs – think Virgil Van Dijk, who cost Liverpool £75 million, but helped finally end their wait for a Premier League crown.

Others are simply disasters. And to be honest are hilarious.

Not everyone is cut out for the Premier League, so here are the five worst signings ever made.

5. Alexis Sanchez, Arsenal to Manchester Utd in 2018 | Swap deal for Henrikh Mkhitaryan

Incredibly this seemed like a massive coup at the time. Alexis Sanchez had scored 24 goals in the 2-16-17 Premier League season for Arsenal, netted a goal in their FA Cup Final win, and was shortlisted for Player of the Year. The following season he scored seven goals in the opening half of the campaign before dramatically moving to Old Trafford in the January transfer window.

This was massive at the time and sent loyal Gooners into meltdown. But Arsenal had the last laugh.

Sanchez made 45 appearances for United over the course of 18 months and scored just five times – averaging a goal every nine-and-a-half hours of football.

The kick in the gut for United fans was a blow to the bank balance as well, as Sanchez was on nearly £400,000 a week and had £1.1 million in annual bonuses. Even when they shipped him out on loan to Inter Milan in 2019, he was costing the Red Devils £200,000 a week.

He left in August 2020 on a free transfer.

4. Andriy Shevchenko, AC Milan to Chelsea in 2006 | £39.5 million

This was a British record fee at the time and was a power move by Chelsea owner Roman Abramovich, who had been trying to get Shevchenko to join the Blues for years. The Russian striker was nearly 30 years old, but had been firing on all cylinders for Milan, scoring 24, 17, and 19 league goals in his last three seasons.

That red-hot form disappeared in London.

Shevchenko played 48 times for Chelsea, but scored just eight goals – an average of a goal every six games. He was constantly picking up injuries while Didier Drogba was in unreal form alongside him, meaning Shevchenko was shuffled to the back of the pack.

Jose Mourinho and Abramovich never saw eye to eye on the signing, and it eventually cost "The Special One" his job in 2007. Shevchenko went back to Milan on loan in 2008 and eventually returned to Dynamo Kyiv in 2009 on a free transfer.

3. Mario Balotelli, AC Milan to Liverpool in 2014 | £18 million

Liverpool had just lost Luis Suarez, so there was a big hole to fill in Brendan Rodgers’ team. Balotelli had already lit up the Premier League with his antics at Manchester City, but he was still only 24 years old and had just scored 26 goals in 43 Serie A games for Milan.

But Mario was simply shocking at Anfield. He played just 16 league games under Rodgers and scored just once. Rodgers publicly criticized him and said Balotelli was the last available choice to replace Suarez, before Rodgers himself got the boot.

Balotelli was sent back to Milan on loan and when he returned to Liverpool, Jurgen Klopp was the man in charge. Klopp had no interest in Balotelli, so he left for Nice on a free transfer.

2. Bebe, Vitoria Guimaraes to Manchester United in 2010 | £7.9 million

Bebe had never played at a level higher than the Portuguese Third Division, and once had even appeared for Portugal in the Homeless World Cup. But for some reason former Man Utd assistant Carlos Queiroz recommended the striker to Sir Alex Ferguson, and without ever bothering to see him play, Fergie shelled out nearly £8 million for him.

Bebe made just two league appearances for United, totalling a whopping 74 minutes of action.

They quickly discovered he wasn’t up to scratch and he had loan spells at Besiktas, Rio Ave, and Pacos de Ferreira before eventually signing for Benfica in 2014.

Incredibly United managed to sell him for £3 million!

1. Danny Drinkwater, Leicester to Chelsea in 2017 | £34.1m

Drinkwater had been a key part of Leicester’s title winning team a year earlier, so it was no surprise that Chelsea forked out more than £34 million to snap him up in the summer of 2017. But things did not go to plan.

Drinkwater played just 12 times in his debut season under Antonio Conte, then in the next season played in the Community Shield under Maurizio Sarri before never being seen in a Chelsea kit again.

He got shipped out on loan to Burnley, but injured his ankle after getting into a fight at a nightclub and only made one appearance there. He was then loaned to Aston Villa where he made four appearances including a 6-1 hammering by Man City, but was sent back to Chelsea again after head-butting a teammate at training.

He is now on loan at Turkish club Kasimpasa, but this is his fifth season with Chelsea, and he is still reportedly on £100,000 a week. Ouch.

Dishonorable Mention: Ali Dia, Free transfer to Southampton in 1996

I didn’t include Dia on this list as it wasn’t catastrophic financially nor did it cost anyone a job, but the story is remarkable. A man phoned manager Graeme Souness pretending to be the World Player of the Year George Weah. The caller recommended his cousin Ali Dia, claiming he had just scored two goals for Senegal and had played at PSG before moving to Germany. Souness bought him in on a trial – not realizing that the caller had made it all up, and Dia was a 31-year-old college student.

Dia was incredibly named on the bench for a league game against Leeds, and because of an injury to Matt Le Tissier, Dia came on after 32 minutes. It took less than an hour for Souness to realize his mistake and Dia was subbed back off, never to be seen on a pitch again.