With Trent Alexander-Arnold’s move to Real Madrid now confirmed, we look at five of the most controversial free transfers in English football history. Featuring financial disputes, protracted chases, betrayals of trust and more…
5) James Milner
Comfortably the least controversial on the list. Since joining from Aston Villa for 2010, James Milner had proven himself to be the ultimate squad player for Manchester City, capable of featuring out wide, in the middle of the park or even at full-back.
However, the dependable Yorkshireman aspired to be more than a useful utility man, seeking more starts than he had been awarded by Roberto Mancini and, more recently, Manuel Pellegrini.
Milner’s situation had a number of clubs on high alert. A versatile 29-year-old with international experience, a winning mentality and a professional attitude attracted interest from across Europe, but Liverpool won the race for his signature on a free transfer.
Milner would complete his medal collection at Anfield, coming off the bench to play a part in Liverpool’s 2019 Champions League triumph and collecting a Club World Cup winner’s medal in addition to further league and domestic cup success.
4) Paul Pogba
Back in 2011, a young French player was making waves in Manchester United’s academy. One month shy of his eighteenth birthday, Paul Pogba was first drafted into the United senior squad for an FA Cup Fifth Round tie. His potential was undeniable: by the end of the following season, he had moved from the under-18s up to the first team, featuring seven times across all competitions.
It looked as though Pogba was being primed to become the next young star to come through at Old Trafford, but those hopes were shattered when he turned down a new contract, joining Italian giant Juventus on a free transfer.
Sir Alex Ferguson was openly critical of Pogba’s behaviour around the move, claiming he had disrespected the club. For his part, Pogba suggested that the legendary manager’s lack of faith in his ability was a key factor behind the departure, pointing to his lack of game time during a midfield injury crisis.
Pogba delivered on that early promise in Turin, lifting the Serie A title in each of his four seasons with The Old Lady. In 2016, he made a sensational return to United – but this time, the transfer was for a world-record fee. His second stint in Manchester also proved tumultuous, characterised by flashes of brilliance, inconsistent form and frustrating injuries.
3) Trent Alexander-Arnold
“Somewhere I want to stay for the rest of my career is Liverpool…I want to become captain one day. That’s definitely a dream of mine.”
Those were the words of a 20-year-old Trent Alexander-Arnold in October 2018. The West Derby boy made 33 appearances for his beloved Liverpool the previous season, and made his England debut that summer.
The academy product fast became one of the first names on the teamsheet, an integral part of a side that lifted every major honour across a four-year period. A buccaneering presence down the right with an extensive passing range, he was often considered one of the world’s great full-backs, though questions were occasionally asked of his defensive qualities.
As his contract ran into its final year, Trent’s future became the subject of intense speculation, with a transfer to Real Madrid the most likely outcome. Rather than table a transfer offer, the Spanish giants opted to sign the England star on a free transfer at the end of the 2024-25 season (though they may yet pay a nominal fee in order to acquire him ahead of the Club World Cup).
The loss of a homegrown talent, the lack of financial remuneration for the club and the protracted nature of the transfer was the source of much debate and consternation amongst the Liverpool fanbase – and will likely rumble on for a few weeks yet!
2) Steve McManaman
Trent isn’t the first Liverpudlian to controversially leave Anfield for the Bernabeu.
Steve McManaman went from the club’s brightest prospect to one of the league’s most influential creators. He won the FA Cup at 20 and the League Cup at 23, but while McManaman continued to excel individually, Liverpool struggled to compete for top honours.
Contract disputes and transfer wranglings – including a failed attempt by the club to sell the playmaker to Barcelona – ultimately saw McManaman seek a new challenge abroad. In February 1999, he announced that he was departing Merseyside for Madrid. Purportedly underpaid at Liverpool, Macca’s upcoming £60,000 a week contract made him the highest-earning British player in history (for two years).
The Bosman ruling had only come into effect in December 1995, allowing players to change clubs without a transfer fee upon the expiry of their contracts. By 1999, a number of European players had used the rule to move on a free transfer, but McManaman was the first high-profile player from England to do so.
In Madrid, McManaman became one of the country’s most successful exports. A jinky, fleet-footed winger in his earlier days, Macca’s footballing intelligence and link-up play endeared him to teammates and supporters alike. He won two titles and two Champions Leagues with Los Blancos, and is revered by Real fans to this day.
Over time, the animosity from Liverpool fans thawed, too. He was most recently named as one of the 100 Players Who Shook The Kop, ahead of local heroes Ian Callaghan, Phil Thompson and Tommy Smith, and just one place behind Kevin Keegan.
1) Sol Campbell
One of the greatest centre-halves in Premier League history, opinions of Sol Campbell are often shaped by what side of North London you hail from.
To Tottenham Hotspur fans, Sol was one of the club’s greatest homegrown talents (albeit one who started his career at West Ham); the resolute club captain who led the team to their first trophy in eight years.
Towards the end of the decade, the centre-half had grown increasingly disillusioned for a number of reasons at White Hart Lane and, with his contract running down, was considering his options. Recently, Campbell claimed on The Overlap podcast that the Spurs hierarchy attempted to use a post-match assault charge as leverage in negotiations (the false charge, which claimed that Campbell had broken the arm of a match steward, was later dropped).
Unbeknownst to Spurs fans – and indeed, most of the football world – one of the options up for consideration was Arsenal. The 26-year-old, at the peak of his game and one of the country’s most sought-after defenders, took advantage of the Bosman ruling to join Tottenham’s fiercest rivals without so much as a penny changing hands.
Campbell was branded ‘Judas’ by apoplectic supporters: those bitter feelings still runs deep in some sections today. From Sol’s perspective, it proved to be an astute career move: he added two Premier League and two FA Cup winners’ medals to his collection during his six years at the club, and was an integral part of Arsene Wenger’s backline during the famous Invincibles season of 2003-04.