Man Utd's 10 biggest transfer sale mistakes

Stuart Telford

• 16 Oct 2023 02:30 CDT
• 7 min read

Manchester United are one of the most successful clubs in football history with a record 20 English league titles as well as being three-time European champions, but they haven't always got things right in the transfer market.

From the Busby Babes to the Class of '92, United have a rich history of promoting players from their youth academy, and they have invariably been supplemented with some stunning transfer business.

But for every Wayne Rooney there has been a Paul Pogba; the former was signed for €37 million and went on to become United's all-time record goal-scorer, while the latter is their record signing who has twice left on a free transfer to Juventus.

FootballTransfers looks at Man Utd's 10 biggest transfer sale mistakes…

Jaap Stam - €25.8m (Lazio, 2001)

Years before the Nemanja Vidic and Rio Ferdinand partnership, Jaap Stam was the defensive fulcrum upon which United's continental treble in 1999 was built. The Dutchman was a colossus at the back, widely regarded as one of the best centre-backs in the world.

But he made the cardinal error of crossing Ferguson into his third season at Old Trafford, lifting the lid on United's approach to sign him from PSV Eindhoven in 1998 and criticising some opposition players in his autobiography.

Ferguson sold him to Lazio, replaced him with a 35-year-old Laurent Blanc, and later admitted Stam was his biggest mistake as a manager. "When I think of disappointments, obviously Jaap Stam was always a disappointment to me," he wrote in 2013. "I made a bad decision there."

David Beckham - €37.5m (Real Madrid, 2003)

United's Class of '92 boasted Ryan Giggs, Paul Scholes, Nicky Butt and the Neville brothers Gary and Phil, but none developed as big a profile in English football as David Beckham did at Old Trafford.

A goal from the halfway line against Wimbledon delighted Ferguson; Beckham's subsequent relationship with Spice Girl Victoria did not.

Beckham's celebrity lifestyle rankled with the Scot, and after a dressing room row which saw Beckham's head cut by a flying boot, he was allowed to leave for Madrid.

The €37m fee was relative peanuts for the most marketable player in world football at the time, and it wasn't until three seasons later that Ronaldo really started exploding into the player he would eventually become wearing Becks' old No.7 jersey.

Roy Keane - Free (Celtic, 2005)

Long-time club captain Roy Keane fell foul of Ferguson's judgement in 2005 after criticising some of the club's younger players in an analysis video for MUTV, and was released in November of that year, joining Celtic in December.

Keane may have been 34 at the time, but United struggled to replace him, with Kleberson, Eric Djemba-Djemba and even converted forward Alan Smith all tested in his old position in front of the United defence. None worked.

Gerard Pique - €5m (Barcelona, 2008)

If Man Utd had a Class of '92, then Barcelona had a Class of '87 - named after the year they were born in rather than the year they broke through - which starred Lionel Messi, Cesc Fabregas and Gerard Pique. While Messi stayed at Camp Nou, Fabregas and Pique were poached by Arsenal and Man Utd respectively.

But for four years at United, Pique found himself on the bench watching on as Rio Ferdinand, Mickael Silvestre and then Nemanja Vidic dominated the central defensive positions. Frustrated with his first-team opportunities, Pique returned home for just €5m in 2008.

More than 600 games, eight La Liga's, three Champions League's and a World Cup and European Championship with Spain later, and Pique goes down as one of the greatest centre-backs of his generation. United stole Pique in his youth; Barca stole him back on the cusp of his prime.

Cristiano Ronaldo - €94m (Real Madrid, 2009)

Cristiano Ronaldo had wanted to leave a year earlier, but was persuaded by Sir Alex Ferguson to stick about for another season, and still fetched the Red Devils a then world record €94m when he did eventually join Real Madrid in 2009.

But there is no escaping the fact that Ronaldo blossomed into one of the greatest players of all-time at the Bernabeu, scoring a barely fathomable 450 goals in 438 games with Real, as well as contributing 131 assists.

Four of his five Ballon d'Or wins were won with Los Blancos, as were four of his five Champions Leagues. United fans can't help but wonder what might have been.

Paul Pogba - Free (Juventus, 2012 & 2022)

Paul Pogba might go down in history as the worst piece of transfer business ever done by any club, let alone Manchester United. Signed as an academy player from Le Havre in 2009, Pogba was promoted to the first team in 2011, and promised significant minutes.

When Rafael - a full-back - was paired with Park Ji-sung in midfield in a defeat to QPR in 2012, Pogba decided to try his luck at Juventus instead. He blossomed into one of the most potent midfielders in the world in Turin, and was bought back for a then world record €105m in 2016.

But Pogba struggled to recapture his form at Old Trafford. At Juve he had been at the point of midfield with Andrea Pirlo and Claudio Marchisio behind him; at United he was used in multiple different midfield roles by five different managers.

The Red Devils took their eye off his contract situation, and he returned to Juve on free once again in 2022.

Wilfried Zaha - €3.8m (Crystal Palace, 2015)

Wilfried Zaha goes down as a significant transfer mistake on Man Utd's part. An England U21 winger at the time, United did well to acquire Zaha from Crystal Palace ahead of the competition in 2013, but then never gave him a chance.

He was loaned straight back to Palace twice, with a spell at Cardiff in between, and made a sum total of four appearances with United before being sold back to his first club for just €3.8m in 2015.

Zaha was then one of the Premier League's most exciting wingers for several years, with Arsenal wanting to sign him for several years before he joined Galatasaray in 2023.

To rub salt in the wound, Zaha scored in Galatasaray's 3-2 Champions League win at Old Trafford in October 2023.

Memphis Depay - €16m (Lyon, 2017)

Some may expect to find Memphis Depay on a list of worst Man Utd signings rather than sales, but the Dutchman goes down as a wasted talent at Old Trafford and has proved in the seasons since that he can cut it at the top level with Lyon, Barcelona and the Netherlands.

Memphis arrived from PSV Eindhoven in May 2015, and while seven goals and six assists in 53 games was underwhelming return, he was only given until January 2017 to prove his talent. He subsequently did, and United tried to buy him back before he joined Barcelona.

Romelu Lukaku - €74m (Inter, 2019)

— Football Transfers (@Transfersdotcom) August 21, 2022

Romelu Lukaku's Chelsea struggles may be seared into the minds of English football followers, but the Belgian was Man Utd's top-scoring striker for consecutive Premier League seasons in 2018 and 2019, and Ole Gunnar Solskjaer's decision to let him leave for Inter was a strange one.

Lukaku scored 23 and 24 goals in back-to-back Serie A seasons with Inter, lifting the Scudetto in the second of those seasons, while United laboured with Anthony Martial, Edinson Cavani and Marcus Rashford variously leading the line, and brought Ronaldo back, well past his sell-by date, in 2021.

Chris Smalling - €15m (Roma, 2020)

Chris Smalling was one of the most underrated centre-backs in English football for most of a decade after joining United from Fulham in 2010, and was an England regular who won the Premier League at Old Trafford in his first season and then again in Ferguson's last, in 2013.

Admittedly more of a destroyer than a centre-back who would help build up play, Smalling was nonetheless a snip for Roma at €15m in 2020 having impressed on loan the previous campaign, and Harry Maguire's travails in recent seasons have thrown into sharper light what United had.

Trending

What are the most expensive transfers of all time? The 50 highest fees in history

Osimhen CONTACT made as €81m price confirmed

Premier League managers: Full list of current bosses