7 stars who made humiliating transfers including Henderson and 3 Man Utd flops

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Jordan Henderson has joined an unwanted list of players who have been humiliated by transfer moves (Image: Francois Nel/Getty Images)
Jordan Henderson has joined an unwanted list of players who have been humiliated by transfer moves (Image: Francois Nel/Getty Images)

It has been a humiliating week for Jordan Henderson, with the former Liverpool star set to rip up his contract with Al-Ettifaq after just six months in Saudi Arabia.

Henderson left Anfield in the summer after being tempted by the riches offered by clubs in the Middle East state. But playing in the Saudi Pro League has taken its toll on the England midfielder, who is now returning to Europe.

The 33-year-old will now join an unwanted list of players who have been forced to make humiliating transfers after a matter of months with a new club. That list has grown in recent years, with clubs more willing to splash out on signings.

Seven stars stand out for the most humiliating moves. And here, Mirror Football looks at all seven and how their moves went so badly wrong.

1. Jordan Henderson

We start with the most recent addition to the list, in Jordan Henderson. The midfielder is returning to Europe with his tail firmly between his legs having pledged to help lead a social revolution when he moved to Saudia Arabia in the summer.

Marcel Sabitzer completes Man Utd transfer after last-minute deadline day dash eiqrtihriqdhinvMarcel Sabitzer completes Man Utd transfer after last-minute deadline day dash

But with Al-Ettifaq enduring a miserable season mostly playing in front of embarrassingly low crowds, he will now rip up his contract. Henderson is set to move to Ajax, with his reputation in tatters.

2. Angel Di Maria

7 stars who made humiliating transfers including Henderson and 3 Man Utd flopsAngel Di Maria proved to be a disaster after moving to Old Trafford for a British record fee (Getty Images)

Angel Di Maria arrived at Manchester United for a then-British record fee in the summer of 2014. Having been handed the club's iconic No.7 shirt, hopes were high the Argentine could lead the Red Devils to trophy success.

But injuries and a loss of form led to a miserable debut season at Old Trafford for Di Maria, who was widely judged to be the worst signing of the season. He was shipped off to PSG after just a year with United.

3. Jadon Sancho

7 stars who made humiliating transfers including Henderson and 3 Man Utd flopsJadon Sancho last played for Manchester United in August and is now on loan at Borussia Dortmund (Visionhaus via Getty Images)

Heralded as one of England's brightest young talents when he joined United in the summer of 2021, Jadon Sancho failed to ever live up to the hype. Though he was a regular under Ole Gunnar Solskjaer, the winger found chances harder to come by under Erik ten Hag.

Relations between the Dutchman and Sancho deteriorated beyond repair in September when the winger was banished from United's first-team squad after a falling out. With Sancho refusing to apologise, he was shipped back to Borussia Dortmund on loan.

4. Romelu Lukaku

7 stars who made humiliating transfers including Henderson and 3 Man Utd flopsRomelu Lukaku proved to be a massive flop at Chelsea (Getty Images)

The last big-money buy of Roman Abramovich's reign as Chelsea owner was a club-record move for Romelu Lukaku. But the Belgian quickly proved to be one of the worst signings in Premier League history.

Boss Thomas Tuchel never really looked like he wanted the striker, who scored just eight top-flight goals on his return. With little chance he would have a future at Stamford Bridge, Lukaku was sent back on loan to Inter Milan and is currently on loan at Roma.

5. Alexis Sanchez

7 stars who made humiliating transfers including Henderson and 3 Man Utd flopsAlexis Sanchez left Manchester United wishing they hadn't won the race to sign him (PA)

United beat rivals Manchester City to sign Alexis Sanchez in January 2018, though they were soon wishing they had not won that race. The attacker failed miserably to replicate his stunning form with Arsenal at Old Trafford.

After scoring just five goals in 45 appearances for the Red Devils, Sanchez was frozen out and sent on loan to Inter Milan. That move was turned permanent in 2020, with the Chilean later admitting that he knew joining United was a mistake on his very first day with the club.

6. Robbie Keane

7 stars who made humiliating transfers including Henderson and 3 Man Utd flopsRobbie Keane endured a miserable six months at boyhood club Liverpool (GETTY)

The stage was all set for Robbie Keane to fulfil a boyhood dream when he joined Liverpool from Spurs in 2008. The Irishman had been a Reds fan since childhood and was signed having been a regular goalscorer at Tottenham.

Man Utd deadline day live updates as Sabitzer completes loan moveMan Utd deadline day live updates as Sabitzer completes loan move

But he failed to bring those performance levels to Anfield, scoring just seven goals. The ultimate humiliation came in January 2009 when Liverpool sent him back to Spurs for a fee £8million less than what they had paid six months earlier.

7. Leonardo Bonucci

Leonardo Bonucci had established himself as one of the world's best defenders by the summer of 2017, playing in two Champions League finals for Juventus. AC Milan decided to steal the defender from their Serie A rivals that year.

But the move proved to be a disaster, with Bonucci widely criticised for his performances as Milan finished in a disappointing sixth place. The defender returned to Juve after just a year at the San Siro, winning two more Serie A titles.

Jacob Leeks

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