Britain’s Last Four Transfer Record Signings: Were They Successes or Failures?

Liverpool have made their Premier League title intentions well and truly clear this summer with a series of eye-catching signings that have shaken the English top flight to its very core. The Reds surprisingly romped to the title last season, finishing ten points clear of perennial runners-up Arsenal to secure their second crown in five years. Now, however, they have made their move and are looking to secure a stranglehold on the league for years to come.

After breaking the British transfer record to bring in Bayer Leverkusen’s Florian Wirtz for £116 million, they’re on the brink of adding Hugo Ekitike, Eintracht Frankfurt’s rising star, for £79 million. Wirtz’s technical brilliance and knack for unlocking defences promise to reshape Liverpool’s midfield, while Ekitike’s predatory instincts could solve their current striking woes, led by Darwin Nunez.

Online live betting sites have responded to the acquisitions in kind, slashing odds on Liverpool claiming the title for a second straight year. While Bovada’s live betting odds won’t be available until the first match of the 2025/26 season kicks off at Anfield on August 14th, their outright markets are up and running, and it’s the Reds that are currently the 11/5 frontrunners.

Time and again, sky-high transfer fees have been viewed as statements of ambition, yet not all of these gambles have led to triumph. Britain’s last four record-breaking transfers paint a fascinating picture of varying degrees of success, but were they shrewd investments or cautionary tales?

Moises Caicedo: Brighton to Chelsea – £115m

Before his seismic move to Chelsea in the summer of 2023, Moises Caicedo was Brighton’s midfield metronome, combining defensive authority with calm, precise passing. The Ecuadorian was pivotal in Brighton’s rise to European contention, averaging three tackles and 1.5 interceptions per game during the 2022/23 season, and becoming one of the most sought-after players on the planet in the process.

Chelsea and Liverpool were locked in a race for his signature, but eventually the Blues succeeded, forking out £115m to secure his services. Early stumbles—marked by patchy form and frailty under scrutiny—invited sceptics to question the outlay. Yet he has since regained his form, starring throughout the 2024/5 campaign as the Blues secured a top-four finish; he also won the Conference League, and shockingly romped to a 3-0 victory over PSG in the recent Club World Cup final.

OMG JOÃO PEDRO! +240 looking pretty good in the 1st half 👀

CHELSEA UP 3-0! #FIFAClubWorldCup
pic.twitter.com/oRPGcflpQq

— Bovada (@BovadaOfficial) July 13, 2025

Since then, Caicedo’s stock has risen sharply. His combative energy in key matches helped solidify Chelsea’s midfield. While it’s premature to label him a runaway success, his upward trajectory suggests a promising return on investment. Could this record-breaking gamble pay off long-term? Only consistency will answer that.

Enzo Fernandez: Benfica to Chelsea – £106.8m

Chelsea’s spending spree under Todd Boehly was kicked into a higher gear in January 2023 when they smashed the transfer record to land Enzo Fernandez. Fresh from a World Cup triumph with Argentina—where he was crowned Best Young Player—Fernandez arrived with sky-high expectations. At Benfica, his 2022/23 campaign dazzled; he racked up seven goal contributions in just 17 games while orchestrating play with surgical precision.

He had only arrived in the Portuguese capital six months prior, with The Eagles paying just €18m to sign him from River Plate. The transfer to Stamford Bridge secured an unprecedented mark-up, but since arriving in West London, Fernandez has wasted no time winning over fans.

Filling a leadership vacuum, he was named vice-captain and quickly became Chelsea’s go-to man under pressure. His midfield mastery shone during the Club World Cup, where he dictated tempo and showcased his game-controlling abilities. Chelsea won the tournament, which would lead some to call him a success; however, the Blues are yet to fully translate their spending into Premier League dominance.

Fernandez’s impact suggests they’ve struck gold. At just 24, he looks poised for a decade of consistent excellence.

Jack Grealish: Aston Villa to Manchester City – £100m

Jack Grealish was the jewel in the Aston Villa crown. Boyhood Villans fan, academy product, England international, and captain: what wasn’t to love? Known for his mesmerising dribbling, audacious creativity, and a knack for drawing fouls, Grealish virtually carried Villa to respectability. By 2021, he’d created more chances than any other Premier League player over two seasons, making his £100m price tag understandable—if steep—when Manchester City came calling.

Initially, Grealish struggled to adapt to Pep Guardiola’s system. The freedom he’d enjoyed at Villa was replaced by tactical constraints, and his flair appeared muted. Yet, the 2022/23 season brought redemption. He became a key player as City lifted a historic treble, headlined by their maiden UEFA Champions League success with a 1-0 win in Istanbul against Inter Milan.

However, inconsistency has clouded his influence since, with speculation swirling that City may offload him this summer at a significant loss. Did his transfer work out? His role in City’s treble is undeniable, but his diminishing shine may overshadow his flashes of brilliance.

Paul Pogba: Juventus to Manchester United – £89m

Paul Pogba’s blockbuster £89m return to Manchester United in 2016 was supposed to signal a new dawn. Having left United for Juventus on a free transfer in 2012, Pogba blossomed into a midfield superstar in Serie A, amassing 34 goals and 40 assists in 178 appearances while collecting four league titles.

Reality, however, played out differently. At Old Trafford, Pogba was a riddle. His moments of brilliance—like his match-winning display in the 2017 Europa League final—were too often interspersed with injuries, inconsistency, and tensions with managers, notably José Mourinho. By the time Pogba departed in 2022 (again, on a free transfer), United fans were left wondering what might have been. His transfer, once heralded as game-changing, ultimately left a bitter aftertaste, cementing its place as one of football’s cautionary tales.