The Premier League’s Greatest Almosts: 15 Transfers That Would Have Changed Everything

The Premier League has staged some of football’s greatest careers. It could have hosted even more. Behind the title wins, the dynasties and the broken records lies a parallel universe of deals that were agreed, shaken on, even photographed – and then never happened.

Here are 15 of the biggest transfers that came within touching distance, only to vanish into legend.

Roy Keane to Blackburn Rovers (1993)

Picture Roy Keane in blue and white halves, not red.

It nearly happened. In 1993, the Irish midfielder, then at Nottingham Forest, shook hands with Kenny Dalglish and agreed to join Blackburn Rovers. The contract, Keane has since said, was basically done.

He went back to Ireland. The phone rang. It was Manchester United.

Keane had already given his word to Blackburn, but he chose Old Trafford instead. Seven Premier League titles and the captain’s armband later, that handshake became one of the most consequential near-misses in English football.

Zinedine Zidane to Blackburn Rovers (1995)

Blackburn, again, standing at the door of history.

Fresh from winning the 1994/95 Premier League, Dalglish wanted to strengthen his champions. He brought Zinedine Zidane and his Bordeaux team-mate Christophe Dugarry to the training ground. They met owner Jack Walker. The move was there to be made.

Walker famously killed it with one line: why sign Zidane when you already have Tim Sherwood?

Three years later, Zidane lifted the World Cup and the Ballon d’Or. Blackburn, who could have built around him, instead became the punchline to their own sliding-doors story.

Alan Shearer to Manchester United (1996)

Alan Shearer, the Premier League’s record scorer, chose home over dominance.

In 1996, he sat down with Kevin Keegan and Sir Alex Ferguson on the same day. Manchester United or Newcastle United. Old Trafford or St James’ Park.

By his own admission, Shearer was “90 per cent” sure he would join United. The move would have given Ferguson the most ruthless No 9 of his era at his absolute peak.

Then Keegan called again. The pull of boyhood loyalties and the vision of leading Newcastle’s charge proved stronger. Shearer went home, became a local deity, and left United to win everything without him.

Andriy Shevchenko to West Ham (1999)

Before Ballon d’Ors and Champions League nights, Andriy Shevchenko was a teenager on trial at West Ham.

Harry Redknapp brought the 17-year-old Ukrainian over, lined up a reserve game against Barnet and watched him score twice. The talent was obvious. The price – around £1 million – felt steep for a kid.

Redknapp and assistant Frank Lampard Snr decided it was too much. West Ham walked away. Shevchenko’s career took him to Milan, to a Ballon d’Or in 2004, and eventually to Chelsea.

The Hammers were left with the story of the one that got away for the sake of a million pounds.

Zlatan Ibrahimovic to Arsenal (2000)

Zlatan Ibrahimovic in an Arsenal No 9 shirt exists. As a photograph, not a memory.

At 17, the Malmo striker flew to London, toured the club, posed in the famous red and white with his name on the back. It looked like a done deal.

Then came Arsene Wenger’s condition: a trial first.

Zlatan’s response was pure Zlatan. He refused. “Zlatan doesn’t do auditions,” he would later say. The move collapsed before it truly began.

He wouldn’t arrive in England until 2016, at Manchester United, with a career’s worth of goals and ego already behind him.

Yaya Toure to Arsenal (2003)

Another future Premier League powerhouse briefly wearing Arsenal colours, without ever signing.

At 20, Yaya Toure arrived from Beveren for a trial and played a pre-season friendly against Barnet in July 2003. Wenger wanted him. The club tried to secure a work permit.

Toure grew tired of waiting.

He chose Metalurh Donetsk, where he could move without passport complications. Years later, he would return to England as the heartbeat of Manchester City, winning three Premier League titles and dominating midfields in the way Arsenal had once imagined.

Cristiano Ronaldo to Arsenal (2003)

Ask Wenger for his biggest regret, and he doesn’t mention a final or a title race. He mentions Cristiano Ronaldo.

In 2003, a 17-year-old Ronaldo and his mother sat with Wenger at Arsenal’s training ground. He was shown around, given a shirt with his name on the back. The club wanted him from Sporting Lisbon.

The problem was the fee. Manchester United were willing to go further. Arsenal were not.

Ronaldo moved to Old Trafford, won three Premier League titles, and started a Ballon d’Or collection that would reach five. Arsenal were left with a shirt and a memory.

Ronaldinho to Manchester United (2003)

For a brief window in 2003, it looked inevitable: Ronaldinho in United red.

Ferguson spoke publicly about how close the club were. The Brazilian wanted out of Paris Saint-Germain, United wanted a new star, and the deal seemed all but sealed.

Then Barcelona moved.

Sandro Rosell made his promise, became president, and Ronaldinho chose Camp Nou instead. He won the Ballon d’Or in 2005, lit up La Liga and delivered the Champions League in 2006.

United rebuilt around Cristiano Ronaldo. The Premier League never saw Ronaldinho in full flight.

Rivaldo to Bolton Wanderers (2004)

Some near-misses sound like fantasy. Rivaldo to Bolton Wanderers was almost reality.

In 2004, two years after winning the World Cup with Brazil, the Ballon d’Or winner was a free agent and ready for a new challenge. Bolton chairman Phil Gartside revealed he had a fax in his pocket confirming Rivaldo wanted to join and had accepted the financial terms.

Rivaldo himself spoke of the appeal: dragging Bolton into Europe for the first time in their history.

It never happened. Talks stalled, the deal faded, and Rivaldo signed for Olympiacos instead. Sam Allardyce’s collection of big names never quite reached that level of surreal.

Steven Gerrard to Chelsea (2005)

Fresh from Istanbul and the miracle of 2005, Steven Gerrard almost walked away from Liverpool.

Jose Mourinho wanted him at Chelsea. Desperately. He pictured a midfield of Claude Makelele, Gerrard and Frank Lampard – a blend of steel, brain and goals that might have dominated Europe for years.

Gerrard even handed in a transfer request. He has admitted he was tempted by Mourinho, his head turned by the chance to join the reigning English champions.

Then came the conversations at home. The weight of Anfield, of his own story, pulled him back. Gerrard signed a new four-year deal and stayed another decade.

Chelsea built dynasties without him. Gerrard remained Liverpool’s eternal captain, his almost-move to Stamford Bridge adding another layer to an already dramatic career.

Aaron Ramsey to Manchester United (2008)

For a few days in 2008, Aaron Ramsey was a Manchester United player in all but signature.

United announced on their website that they had agreed a fee with Cardiff City for the 17-year-old, describing him as one of Wales’ brightest prospects. It looked routine: the champions moving early for a rising talent.

Then Arsenal moved faster off the pitch.

Wenger, working as a pundit at Euro 2008, flew Ramsey over, carved out time during the tournament and laid out his vision. The personal touch worked.

Ramsey chose Arsenal, spent 11 years in north London and scored the winning goal in two FA Cup finals. United’s announcement became a footnote in someone else’s story.

Robert Lewandowski to Blackburn Rovers (2010)

Blackburn Rovers and fate crossed paths again in 2010, this time with Robert Lewandowski.

Rovers had done the groundwork. They had a proposal in place with Lech Poznan, talks with the player were positive, and a visit to England was arranged so Lewandowski could see the club and the stadium.

Then a volcano erupted.

Eyjafjallajokull’s ash cloud shut down European airspace. Lewandowski never made the trip. Without that visit, Blackburn lost their advantage.

He joined Borussia Dortmund instead, then Bayern Munich, then Barcelona, and became one of the most prolific scorers of his generation. Blackburn slipped down the divisions with a story that sounds too wild to be true.

Kylian Mbappé to Arsenal (2016) and Liverpool (2017)

Kylian Mbappé’s rise looked unstoppable from the moment he broke through at Monaco. Two Premier League giants tried to get in on the ground floor.

In 2016, with Mbappé still 17 and yet to sign his first professional contract, Wenger took a plane to the south of France. He sat in the family home, tried to sell Arsenal as the place to grow into superstardom.

A year later, Jürgen Klopp took his shot. Liverpool flew Mbappé and his family on a private jet, circled in the air, talked, ate, pushed as hard as they could.

Both pitches failed. Mbappé chose Paris Saint-Germain, won the World Cup with France and dominated Ligue 1 before finally heading to Real Madrid.

Arsenal and Liverpool were left to imagine what he might have looked like in their colours, terrorising Premier League defences.

Erling Haaland to Manchester United (2019)

Erling Haaland’s Premier League story now belongs to Manchester City. It could have started in red.

In December 2019, Ole Gunnar Solskjaer, then Manchester United manager, flew to Austria to meet his former Molde striker. He had already urged United to sign Haaland 18 months earlier, before the goals at Red Bull Salzburg turned him into a global target.

United moved late. Borussia Dortmund moved decisively.

Haaland chose the Bundesliga, then crossed to City, where he has already collected two Premier League titles and three Golden Boots. Solskjaer has since recalled how he told United “you have to sign this boy”.

They didn’t. Their city rivals did.

Jude Bellingham to Manchester United (2020)

Another generational talent, another near-miss at Old Trafford.

In 2020, 17-year-old Jude Bellingham and his family visited United’s Carrington training ground. The club rolled out its royalty: Solskjaer, Sir Alex Ferguson, Bryan Robson, Eric Cantona. They talked, they sold the vision, they thought they had him.

Robson has said they left that meeting convinced Bellingham would sign.

He didn’t. He chose Borussia Dortmund, then Real Madrid, and has since become one of the most complete midfielders in the game.

United, once again, were left with the sense that they had been at the table, said the right things, and still watched the future walk away.

Football history is built not just on the transfers that happen, but on the ones that don’t. How different would the Premier League look if even two or three of these deals had gone through?