Sir Alex Ferguson’s 6 biggest Man Utd transfer regrets after new Karim Benzema reminder

Manchester United legend Rio Ferdinand has recalled the time Sir Alex Ferguson thought he was about to sign Karim Benzema, prior to the Frenchman’s move to Real Madrid

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Sir Alex Ferguson’s career honours as a player and manager

Rio Ferdinand has claimed that Sir Alex Ferguson failing to bring Karim Benzema to Manchester United is one of the legendary manager’s “biggest regrets”.

Ferguson – more often than not – got it spot on when it came to his transfer dealings. On three separate occasions, across as many decades, the Scot built title winning sides through a combination of academy graduates and shrewd recruitment.

But along with some high-profile misses (step forward Kleberson, Eric Djemba Djemba and Bebe), Ferguson was left ruing some of the deals he never quite managed to get over the line. Ferdinand has recalled how Ferguson told his central defender that he would be signing Benzema, after the Lyon striker had given him the runaround, only to lose out to Real Madrid.

Not quite in the realms of his old adversary Arsene Wenger, Benzema is the lastest in Fergie’s unwanted list of names that may still give him some sleepless nights.

Alan Shearer

Arguably the most famous near-miss of Ferguson’s near 30-year stint in the dugout, Alan Shearer himself admits that upon leaving Blackburn he was going to join Manchester United. The England international, well on his way to becoming the greatest Premier League marksman of all time, had also met with Newcastle.

However, Ferguson was confident he would get his man. After all, he always did. The United boss had already missed out on him once before he joined Rovers and had no intention of it happening again. “I’d actually done a deal as far as Alan Shearer’s contract was concerned, we’d come to a settlement,” the club’s former chairman Martin Edwards revealed.

Sir Alex Ferguson hoped to sign Alan Shearer after his heroics to help Blackburn win the title


Popperfoto via Getty Images)

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Fergie promised Shearer the No.9 shirt and felt it was a matter of time before he signed on the dotted line. But after three days of waiting, Shearer’s agent confirmed his client’s intention to sign for his beloved Newcastle. “At any rate, there was clearly an undisclosed agenda, and one day I’ll find out what really happened,” a furious Fergie later said.

Shearer ended his career with the solitary title he won at Blackburn and the prospect of him plundering goals at Old Trafford remains an untapped one.

Paul Gascoigne

In his own words, failing to sign the maverick midfielder was the greatest disappointment of his managerial career.

Like Shearer, Ferguson felt that United were in pole position to land Gascoigne as he looked to leave Newcastle. “For me the most disappointing of all was Paul Gascoigne. He was the best player of his era, a breath of fresh air because he played with a smile,” he later admitted.

Paul Gascoigne turned down Man Utd to instead sign for Tottenham


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“We spoke to him and the night before I went on holiday, he says, ‘Go and enjoy yourself, Mr Ferguson, I’ll be signing for Manchester United.’

“So I went on my holidays but Martin Edwards (then chairman) rang and said ‘I’ve got some bad news – he signed for Tottenham. They bought a house for his mother and father in the north east and that swung it’. I think it was a bad mistake, and Paul admits it.”


Barcelona won the race to sign Ronaldinho in 2003



So near, but so far. Having sold David Beckham to Real Madrid in the summer of 2003, United knew they needed a high profile signing to bridge the gap. Ronaldinho fit the bill, 12 months of breaking English hearts in the World Cup and on the back of a season breaking ankles in Ligue 1 with PSG.

“There was a problem with his brother, who was his agent, but Peter Kenyon, who was chief executive then, didn’t get the job done,” the former United manager said. Ironically, had Beckham gone to the Camp Nou, the Red Devils would have had a free run at Ronaldinho.

Instead they had to settle for a consolation prize of a Portuguese youngster from Sporting…wonder how he got on?

Eden Hazard

Fergie felt £34m was too steep for Lille starlet Eden Hazard…not the best decision in hindsight


AFP/Getty Images)

United were firmly in the mix to sign the tricky Belgian winger as Lille prepared to cash in on one of the most talented players in their history. Along with interest from Old Trafford, Man City and Chelsea also made it clear they wanted to sign him.

Hazard ended up at Stamford Bridge signing for £34million. And United? They ended up with Shinji Kagawa from Borussia Dortmund, a deal Fergie felt represented better value for money.

“There is a borderline in terms of what you would think is a good signing for United,” Ferguson explained during Kagawa’s unveiling. “I see some values on players, like Hazard for instance. To me it was a lot of money. He’s a good player, but £34million?”…Ooft.

Aaron Ramsey

Man Utd had announced they had agreed a fee to sign Aaron Ramsey, only for him to sign for Arsenal

They may be a daily occurrence nowadays, but there was a time when United were well known for their lack of PR disasters. That wasn’t the case in 2008 with their failed pursuit of a young Ramsey, plastering the news that they had agreed a deal to sign him on their official website, only to miss out.

“United have agreed a fee with Cardiff City to bring talented teenager Aaron Ramsey to Old Trafford,” a press release read. At the bottom of the statement, it was confirmed three other clubs had agreed a fee, no worries though, right?

Well not until the Welshman picked Arsenal of course. “I had to make a decision at the time. I flew over to see the boss [Wenger] and I knew straight away that this was where I wanted to be, I wanted to be in his plans and I was just buzzing,” he later recounted.

Jaap Stam

Jaap Stam was allowed to leave Man Utd after comments about Sir Alex in his autobiography



The outlier on this list in the fact that Ferguson’s regret stems from allowing a player to leave, rather than not signing them in the first place. Stam had established himself as one of the best central defenders in the world, but after some unflattering remarks about the boss in a 2001 autobiography, he was given the boot.

“I can say we have accepted a bid from Lazio and the rest is up to the player,” he said after leaving him out against Aston Villa. “We know that Wes Brown is going to be a marvellous player. “In my opinion he is going to be the best centre-half in the country and he has his opportunity now.”

And while Brown had a perfectly serviceable career, he never reached the heights of Stam and in the years following his departure, United endured – in Fergie terms – a relatively barren few seasons.

“When I think of disappointments, obviously Jaap Stam was always a disappointment to me,” he said in 2013. “I made a bad decision there.”

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