The Premier League's Greatest What Ifs: 15 Transfers That Could Have Changed History

The Premier League has housed some of football’s greatest names. Yet its history is also built on near-misses – handshakes that never became signatures, flights that never took off, and teenagers who slipped through the net.

Fifteen deals. Fifteen sliding doors. Here are the transfers that almost rewrote English football.

Blackburn’s Parallel Universe: Keane, Zidane… and Lewandowski?

Roy Keane to Blackburn Rovers (1993)

Roy Keane should have been a Blackburn player. Not in theory. In practice.

In 1993, the Irish midfielder agreed a deal with Kenny Dalglish, shook hands, and went back to Ireland believing he was heading to Ewood Park. “I did shake hands… and I said, ‘Listen, I’ll come’,” Keane later recalled. The contract, he said, was “basically agreed”.

Then Manchester United called. Keane made what he describes as his “mistake” – telling Blackburn he would sign, then choosing Old Trafford instead. Seven Premier League titles later, four as captain, it became one of the most consequential U-turns in English football.

Zinedine Zidane to Blackburn Rovers (1995)

Two years on, Dalglish tried to add a young French midfielder to his title-winning side. Zinedine Zidane, then at Bordeaux, visited Blackburn’s training ground with Christophe Dugarry. They met owner Jack Walker.

Tim Sherwood remembers the moment – and the line that has echoed through history. Walker reportedly asked: “Why do you want to sign Zidane when we have Tim Sherwood?”

Blackburn walked away. Three years later, Zidane lifted the World Cup and the Ballon d’Or.

Robert Lewandowski to Blackburn Rovers (2010)

Fifteen years after turning down Zidane, Blackburn were back in the frame for another future great. Robert Lewandowski, still at Lech Poznan, had held successful talks. A proposal was in place. The move was ready to be sealed.

Then a volcano erupted. Literally.

The Eyjafjallajokull ash cloud shut down European airspace and Lewandowski never boarded the plane to England. “I could not fly to Blackburn because of the volcano,” he later said. He joined Borussia Dortmund instead, then Bayern Munich, then Barcelona – and became one of the most prolific forwards of his generation.

Blackburn Rovers, who once had Keane almost signed and Zidane in the building, were denied Lewandowski by an Icelandic volcano. Few clubs have come closer to a dynasty without ever starting one.

United’s Near-Misses: Shearer, Ronaldinho, Haaland, Bellingham

Alan Shearer to Manchester United (1996)

Manchester United wanted the most lethal striker in England. Alan Shearer listened.

In 1996, the Premier League’s all-time top scorer sat down with Sir Alex Ferguson and Newcastle boss Kevin Keegan on the same day. “At one point I was going to go to Manchester United,” Shearer admitted. “I was 90 per cent certain I was going to go there.”

Then Keegan called again. The pull of his boyhood club won. Shearer chose Newcastle for a world record £15 million, scored 148 Premier League goals for them and turned down a place in what became Ferguson’s treble-winning juggernaut.

Ronaldinho to Manchester United (2003)

Seven years later, United closed in on another superstar. Ronaldinho had decided to leave Paris Saint-Germain and Old Trafford looked like his next stop. Ferguson even said: “We are just about there… We are very close.”

The deal never landed. Barcelona moved faster. Sandro Rosell made his pitch: if he became president, would Ronaldinho join? The Brazilian said yes.

He went on to win the Ballon d’Or in 2005 and the Champions League in 2006, dazzling at Camp Nou instead of the Stretford End. United, denied Ronaldinho, turned to a teenage winger from Sporting Lisbon. His name was Cristiano Ronaldo.

Erling Haaland to Manchester United (2019)

The Haaland saga had a different twist. In 2019, Ole Gunnar Solskjaer flew to Austria to convince his former Molde striker to join United from Red Bull Salzburg. He knew the talent. He had already urged the club to sign Haaland 18 months earlier.

“The summer before I came, I rang the club and said, ‘You have to sign this boy, he is going to be absolutely top class’,” Solskjaer later revealed. United waited. By the time they moved, Borussia Dortmund were in the race – and won it.

Haaland eventually arrived in Manchester, but in sky blue. Two Premier League titles and three Golden Boots later, the regret at Old Trafford is obvious.

Jude Bellingham to Manchester United (2020)

Bellingham’s visit to Carrington felt like a statement. United rolled out the greats: Ferguson, Bryan Robson, Eric Cantona. Solskjaer was there too. The club pitched its history, its pathway, its prestige.

“We all spoke to him and we sold it as well as he could,” Solskjaer recalled. Robson added: “After that meeting we thought he was coming to us.”

He didn’t. Bellingham chose Borussia Dortmund, then Real Madrid. Another generational talent slipped away, another “almost” that now looks seismic.

Wenger’s Arsenal: The Nearly Team Before the Nearly Teams

Few managers in modern football have sat closer to greatness than Arsene Wenger. He saw it, shook hands with it, sometimes even put a shirt on it – then watched it walk away.

Zlatan Ibrahimovic to Arsenal (2000)

At 17, Zlatan Ibrahimovic flew from Malmo to London. Arsenal had a No 9 shirt with “Ibrahimovic” on the back. He posed for photos in it. The move seemed inevitable.

Then came Wenger’s condition: a trial first. Ibrahimovic was stunned. “Zlatan doesn't do auditions,” he later said. He walked.

He would not reach the Premier League until 2016, when he joined Manchester United instead, by then a global superstar with a career built on the swagger that first took him out of London.

Yaya Toure to Arsenal (2003)

That same summer, a 20-year-old Yaya Toure arrived from Beveren for a trial. He even played in a pre-season friendly against Barnet in July 2003. Wenger wanted to sign him.

But the work permit dragged on. Toure grew impatient and chose Metalurh Donetsk, where he could move without passport complications. “Yaya Toure had an agreement with us,” Wenger later said. “It’s not because we did not want to sign him… He preferred to go to Metalurh Donetsk.”

Toure would eventually dominate midfields for Manchester City, winning three Premier League titles between 2010 and 2018. Arsenal had him in their shirt, briefly, before watching him transform a rival.

Cristiano Ronaldo to Arsenal (2003)

The one that still haunts Wenger.

In 2003, a 17-year-old Cristiano Ronaldo and his mother visited Arsenal’s training ground. Wenger hosted them, showed them around, and even handed the teenager a Gunners shirt with his name on the back. “We were very close,” Wenger said later.

The deal broke on the rocks of the transfer fee. Manchester United paid it. Ronaldo left England with three Premier League titles and five Ballons d’Or to his name. Wenger has since called missing out on him his biggest regret.

Aaron Ramsey to Manchester United (2008)

This time it was Arsenal who stole in. Manchester United announced they had agreed a fee with Cardiff City for Aaron Ramsey, describing him as “one of his country’s brightest prospects”. It looked done.

Ten days later, Ramsey was an Arsenal player. The teenager had been flown out to meet Wenger during Euro 2008. “I felt like he really wanted me,” Ramsey said years later. Lunch, a clear vision, and a personal touch swung the deal.

He stayed 11 years, won three FA Cups, and wrote his own chapter in north London – not at Old Trafford, where his arrival had once been taken for granted.

Kylian Mbappe to Arsenal (2016)

Wenger was still chasing the next great forward in 2016. Kylian Mbappe, then 17 and yet to sign his first professional contract with Monaco, was his target. Wenger flew to the south of France, visited the family home, and tried to bring him to London. “I took a plane… I was at his home with his parents. I tried to convince him to come to Arsenal,” he said.

Mbappe stayed put for another year, then chose Paris Saint-Germain. He became a World Cup winner with France and a superstar in Ligue 1 before eventually joining Real Madrid. The Emirates never saw him in red and white.

Liverpool, Chelsea, and the One That Stayed

Steven Gerrard to Chelsea (2005)

Some transfers would have shaken the league to its core. Steven Gerrard to Chelsea was one of them.

Fresh from dragging Liverpool to Champions League glory in Istanbul, Gerrard was the obsession of Jose Mourinho, who dreamed of a midfield of Claude Makelele, Gerrard, and Frank Lampard. Liverpool’s captain even handed in a transfer request in July 2005.

“I was thinking, ‘I’d love to play for Jose Mourinho’,” Gerrard later wrote. “Jose turned my head.”

The move seemed inevitable. Then came the backlash, the family talks, the pull of Anfield. Gerrard reversed course, signed a new four-year deal, and stayed another decade. The Premier League kept one of its defining one-club icons. Mourinho’s fantasy midfield never existed.

Kylian Mbappe to Liverpool (2017)

Liverpool, too, had their shot at Mbappe. In 2017, Jurgen Klopp and the club hierarchy went all out. They met Mbappe and his family on a private jet, flying in circles while Klopp made his case. “Liverpool really pulled out all the stops,” he later said. There was talk, food, a full charm offensive.

Mbappe still chose PSG. Liverpool built a Champions League and Premier League-winning side without him, but the thought of the French forward in Klopp’s high-octane attack lingers.

West Ham, Bolton, and the Almost-Icons

Andriy Shevchenko to West Ham United (1999)

Long before he arrived at Chelsea, Andriy Shevchenko spent a trial spell in east London. West Ham, under Harry Redknapp, arranged a reserve game against Barnet. The 17-year-old Ukrainian scored twice.

Redknapp and assistant Frank Lampard Snr liked what they saw. The problem was the price. “He was like £1 million,” Redknapp later recalled. “I remember talking to Frank Lampard Snr. after and saying, ‘That is too much money’. He was only 17 at the time, so we didn’t take him.”

Shevchenko went on to win the Ballon d’Or in 2004 and become one of Europe’s deadliest strikers. West Ham walked away at £1 million.

Rivaldo to Bolton Wanderers (2004)

If Lewandowski to Blackburn sounded improbable, Rivaldo to Bolton bordered on fantasy. But in 2004, it came close.

Chairman Phil Gartside said he had a fax in his pocket confirming Rivaldo wanted to come. The World Cup winner and Ballon d’Or holder had agreed terms financially. “It’s just a case of getting together with him to put pen to paper,” Gartside said after a win at Everton.

Rivaldo himself spoke of wanting the challenge of pushing Bolton into Europe for the first time. It never happened. The Brazilian signed for Olympiacos instead, and the Premier League never saw him in white.

The One That Got Away… Twice: Mbappe

Mbappe’s name threads through this list like a warning to every recruiter in England.

Arsenal tried. Liverpool tried. Both managers flew, met the family, made their pitch. Both were turned down. Mbappe chose PSG, then Real Madrid, bypassing the Premier League entirely despite the league’s financial might and global pull.

He is the modern symbol of a theme that runs through every era of this story: even the richest, most powerful clubs cannot sign everyone. Some of the greatest players in history walked through their doors, shook their hands, heard their offers – and still said no.

Football history is often told through the players who arrived. The trophies they lifted. The goals they scored.

But these 15 almost-transfers remind us of the other side of the game: the phone call that changed a mind, the ash cloud that grounded a flight, the trial that never should have been requested, the fax that never led to a signature.

How different would the Premier League look if just three or four of these deals had gone through?