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Jack Grealish & The €100M Club of Disappointment | Seven Star Signings Who Failed Expectations

  Hassan Afolabi August 8, 2025

Jack Grealish & The €100M Club of Disappointment | Seven Star Signings Who Failed Expectations

Jack Grealish is on the verge of ending his time at Manchester City following his inability to sustain any long-term good performances at the club he joined in a £100 million move from Aston Villa in 2021.

Aside from the Englishman, there have been several others who secured big-money moves but failed to meet expectations. Many of these are stars who moved to replace another departed star, with most being associated with La Liga clubs.

As the English winger sets out for the continuation of his adventure elsewhere, we take a look at five other stars who also moved for 100 million deals but failed to live up to expectations.

7 Star Signings Who Failed Expectations

7. Eden Hazard to Real Madrid

Jack Grealish & The €100M Club of Disappointment | Seven Star Signings Who Failed Expectations : Eden Hazard

The worst in the list. Eden Hazard signed for Los Blancos in a €120 million deal from Chelsea in the summer of 2019, with the expectation that he would be their replacement for Cristiano Ronaldo, who left the previous summer.

The move failed woefully as the Belgian failed to make any telling impact in his four years in the Spanish capital—just earning handsomely and costing them more in add-ons to Chelsea—while much of their success came without him contributing any quota.

Hazard scored seven goals and provided nine assists in 76 games before his retirement ahead of the start of the 2023–24 season.

6. Ousmane Dembélé to Barcelona in 2017

Jack Grealish & The €100M Club of Disappointment | Seven Star Signings Who Failed Expectations : Ousmane Dembele

Maybe because of the enormous amount of money received from PSG in the Neymar deal, Barcelona quickly splashed out the cash and brought in young Ousmane Dembélé as the Brazilian's successor.

The Frenchman spent the majority of his time at the club on the injury sidelines, although glimpses of his brilliance were obvious in the short time he was available. But at the time, he could not lock down a starting spot due to his inconsistencies.

When the sun finally started to shine on him, Dembélé was already in the final six months of his contract and was keen on leaving the club. He reached an agreement to sign a contract so that the club could earn a consolation fee from his move to PSG in the summer of 2023.

5. Philippe Coutinho to Barcelona in 2018

Jack Grealish & The €100M Club of Disappointment | Seven Star Signings Who Failed Expectations : Philippe Coutinho

In their attempt to sign Neymar Jr.'s replacement, Barcelona found themselves paying €135 million to Liverpool to secure the services of another Brazilian, Coutinho, in the winter window of 2018.

The midfielder forced a move away from Anfield to fulfil his dream of playing for the Catalan giants, but that ended up as a decision he would regret in his career.

Although he failed at Barcelona, he did enjoy collective success and rekindled his glow during his loan stint at Bayern Munich while still in the books of Barça. Things didn't quite go well for him individually at the club.

He was sold to Aston Villa for less than €20 million in 2022.

4. Antoine Griezmann to Barcelona in 2019

Jack Grealish & The €100M Club of Disappointment | Seven Star Signings Who Failed Expectations : Antoine Griezmann

Although the numbers were satisfying, the Frenchman never reached the level he or Barcelona had hoped for when his release clause of €120 million at Atlético Madrid was triggered in the summer of 2019.

In his two full seasons at Barcelona, Antoine Griezmann faced constant criticism for his inability to influence games as much as he did at his former club. His time at the club also coincided with a period of title drought, as Barcelona didn't win a league title and fell hard in Europe.

He featured in 102 games, scored 35 goals and assisted 16 others across all competitions before his two-year loan to Atlético Madrid, which included an obligation to buy for €40 million if some appearance-based clauses were activated.

In an attempt not to activate the clause, Atlético Madrid resorted to playing Griezmann only in the final 30 minutes of their games, and subsequently finalized an agreement for a permanent move for just €20 million in 2022.

3. João Félix to Atlético Madrid in 2019

Jack Grealish & The €100M Club of Disappointment | Seven Star Signings Who Failed Expectations: Joao Felix

Young João Félix saw himself heading to Atlético Madrid in a €127 million move after his breakthrough season with his boyhood club, Benfica, where he scored 20 goals and eight assists across all competitions.

He was signed on a seven-year contract as Antoine Griezmann's replacement, but struggled to live up to expectations due to inconsistencies, injuries, and tactical issues, as his style did not align with the demands of Diego Simeone's physical setup.

After three and a half years, he was loaned to Chelsea and then Barcelona before signing for the latter in a €52 million deal, finally bringing an end to a mismatch of five years.

2. Romelu Lukaku to Chelsea in 2021

Jack Grealish & The €100M Club of Disappointment | Seven Star Signings Who Failed Expectations : Romelu Lukaku

Romelu Lukaku's famous #Lukwhosback hashtags following his return to Chelsea in the summer of 2021 ended with both parties regretting their decision to reunite.

The Belgian arrived in a €113 million move from Inter on the reputation as one of the best strikers in the world after leading them to the Serie A title in his final season, finally dethroning Juventus after ten years.

Lukaku started well on his return, but his influence soon waned and he was faced with harsh criticism, leading to his return to Italy on loan at Inter and then Roma, before sealing a permanent move to Napoli for just €30 million in the summer of 2024.

1. Jack Grealish to Manchester City in 2021

Jack Grealish & The €100M Club of Disappointment | Seven Star Signings Who Failed Expectations

After helping them gain promotion back to the top flight, Jack Grealish spent two more seasons with Aston Villa before his €115 million British transfer record to Manchester City.

He enjoyed a successful first season with the Etihad landlords, but eyebrows were raised over his productivity. Grealish only managed six goals in 39 games across all competitions.

Unfortunately, that number would be his best at the club as he failed to reach that in his next three seasons, even going over a year without scoring for the club at some point. He eventually lost his spot in the starting XI, and now the club considers him no longer a part of their plans going forward.

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