As Jordan Henderson prepares to put the final touches to his move to Ajax after ending his three-year contract with Al-Ettifaq within six months, it is hard to think if any transfer moves have turned out worse.
Upon taking the decision to leave Liverpool, Henderson made the choice to depart a club that is challenging on all fronts and looks rejuvenated this season at the top of the Premier League under Jurgen Klopp.
The 33-year-old also soiled his reputation by moving to a nation where homosexuality is illegal, with the midfielder previously a big advocate for LGBTQ+ rights during his time at Anfield.
He also endured a dismal time on the pitch at Al-Ettifaq, with Steven Gerrard's side languishing in mid table in the Saudi Pro League, while they have regularly played in front of just a few hundred fans.
Reports also broke on Wednesday that Henderson has not even received a penny of his mouth-watering £350,000-a-week wages at Al-Ettifaq, having deferred payments in the last six months, with sources claiming there is a belief that Henderson will never be paid what he is owed.
In light of Henderson's failed stint in Saudi Arabia, Mail Sport takes a look at some of the other worst transfers of all-time.
Jordan Henderson is set to leave Al-Ettifaq just six months after joining from Liverpool
Henderson's move to Saudi Arabia will go down as one of the worst transfers of all-time
Philippe Coutinho - Liverpool to Barcelona for £105m, rising to £142m - 2017
After a stunning five-year spell at Liverpool, where Philippe Coutinho proved himself as one of the best attacking midfielders in the world, he moved to Barcelona with huge expectations.
However, the transfer was a disaster from the start as the Brazilian was continually blighted by injuries and failed to replicate his form from Anfield.
After a difficult 18 months, he moved on loan to Bayern Munich and even had a hand in knocking Barcelona out of the Champions League, scoring twice in their 8-2 humbling of the Catalan giants in the competition's quarter-finals.
He failed to impress enough in Germany to earn a permanent move and played just 30 times across the following two seasons before joining Aston Villa, who have since loaned him out to Qatari side Al-Duhail.
Philippe Coutinho's move from Liverpool to Barcelona for a potential £142m was disastrous
Eden Hazard - Chelsea to Real Madrid for £88m, rising to £150m - 2019
Like Coutinho, Eden Hazard moved to LaLiga after consistently being one of the best players in the Premier League.
But, the Belgian never really settled with Real Madrid - where he is still their record signing - and in another parallel to Coutinho, he consistently struggled with injuries.
He also failed to cope with the huge expectations placed upon his shoulders as Los Blancos tried to fill the void of Cristiano Ronaldo, who joined Juventus in the previous summer.
Across four years in all competitions, Hazard managed just 76 appearances, 44 of which were starts, scoring seven goals and adding 11 assists.
His final campaign in 2022-23 saw Hazard play 10 times before his contract was mutually terminated, with the attacking midfielder announcing his retirement from the game last October at the age of 32.
Eden Hazard was Real Madrid's record signing in 2019, but ended up retiring four years later
Antoine Griezmann - Atletico Madrid to Barcelona for €120m (£107.7m), sold back two years later for €40m (£34.4m) - 2019
Barcelona signed Antoine Griezmann at the peak of his powers in 2019 after activating his €120m (£107.7m) release clause at Atletico Madrid.
However, the move was made when the club was an absolute mess under controversial president Josep Maria Bartomeu, with Griezmann signed without any thought of where he would play, while Barcelona's players were reportedly against the move.
Antoine Griezmann endured a dire spell at Barcelona after being bought for €120m (£107.7m)
He returned to Atletico Madrid two years later for €40m (£34.4m) and has shone ever since
The Frenchman struggled and his huge contract reportedly ultimately led to the club being unable to renew Lionel Messi's deal in the summer of 2023.
They eventually decided to cut their losses with Griezmann, and loaned him back to Atletico with an obligation to buy for €40m (£34.4m), €80m less than Barcelona had signed him for.
He has since starred for Diego Simeone's side and recently passed Luis Aragones to become the club's record goalscorer.
Mario Balotelli - AC Milan to Liverpool £16m - 2014
Signed as Luis Suarez's replacement, Mario Balotelli was supposed to be the low-risk masterstroke punt from then-Liverpool boss Brendan Rodgers.
However, the Italian failed to fulfill his potential and scored just one Premier League goal, while his time at Anfield was marred by off-field problems.
He returned to AC Milan on loan after one season, before joining Nice on a free transfer the following year.
Meanwhile, Suarez netted 25 times for Barcelona in his inaugural season, and Liverpool finished sixth and were knocked out in the Champions League group stage.
The signing of Mario Balotelli from AC Milan didn't pay off for Liverpool boss Brendan Rodgers
Fernando Torres - Liverpool to Chelsea for £50m - 2011
In one of the most dramatic transfers of all-time, Fernando Torres' move to Chelsea seemed as if it could be one of the top flight's greatest-ever deals.
After scoring 81 goals in 142 games for Liverpool, Torres moved for a then British-record £50m transfer and looked set to take Carlo Ancelotti's side to the next level.
However, Torres completely flopped at Stamford Bridge and joined the long list of Chelsea's big-name striking additions to fail to replicate their previous form.
Although the Spaniard did score 45 times for Chelsea - including a goal against Barcelona in 2012 which secured their place in the Champions League final - those 45 strikes came across 172 appearances, while he became increasingly meme-able following several hilarious misses.
One blunder against Man United, when he rounded David de Gea, before somehow putting his effort wide with the goal gaping, has gone down in folklore.
Fernando Torres was another name in the long list of strikers to flop after joining Chelsea
Paul Pogba - Juventus to Man United for £89m - 2016
Paul Pogba has shown signs of being one of the most talented midfielders of his generation but, unfortunately for Man United fans, this was rarely on display at Old Trafford.
Not only did he leave the club once for free as a teenager, going onto excel at Juventus, but he left again for nothing in 2022 after six largely disappointing years having been signed for £89m.
Pogba's second spell at the club was marred by various injuries and continued speculation about his future, although he did shine during 2018-19 with 16 goals and 11 assists.
However, given United spent £89m on Pogba and let him leave twice for free, the Frenchman is a prime example of the club's dreadful record in the transfer market over recent years.
Paul Pogba left Man United on a free transfer twice, while they signed him for £89m
Alexis Sanchez - Arsenal to Man United for free (swap deal with Henrikh Mkhitaryan)
How can a free transfer be so bad? Well, this bizarre deal with Arsenal which happened via a swap deal with Henrikh Mkhitaryan came after Man United had beaten off serious competition to sign one of the best players in the Premier League.
Alexis Sanchez had 125 goal contributions in 166 games for the Gunners, but was frankly awful after his move to Old Trafford.
Following five goals in 18 months, he was shipped off to Inter Milan, who he ultimately joined on a free transfer after United paid him off.
Despite Alexis Sanchez joining Man United on a free, his move was an absolute disaster
But it wasn't only the on-pitch performance which made this deal a flop. United fought so hard to sign Sanchez that they handed him wages which were reported to be almost £500,000-a-week.
As a result, several other players were put on mega-deals, such as David De Gea's £375,000-per-week which impacted the whole club's salary structure.
Sanchez summed the move up best when reflecting in 2020 as he said: 'I realised a lot of things. After my first training session, I got home and told my family and my agent – can I not rip up my contract and go back to Arsenal?' It never got much better...
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Tanguy Ndombele - Lyon to Tottenham for £63m - 2019
Signed with such high hopes after Tottenham chairman Daniel Levy took the rare decision to sanction an extremely high transfer fee, Tanguy Ndombele has been a complete failure in north London.
The French midfielder - who is the club's record signing - failed to nail down a regular spot in the team under five different permanent managers and, having broken into the France sided before his move from Lyon, Ndombele has added one cap in the past five years.
His low point came in January 2022 after he was booed off the pitch by Spurs fans when they were 1-0 down to Morecambe in the FA Cup.
Ndombele has spent the past three seasons out on loan at Lyon, Napoli and Galatasaray respectively, and the 27-year-old has no future at the club.
Tottenham's £63m move for Tanguy Ndomble has proven to be nothing short of a disaster
Romelu Lukaku - Inter Milan to Chelsea for £97.5m - 2021
Romelu Lukaku's return to Chelsea in the summer of 2021 from Inter Milan was meant to be a triumphant story for a striker who had matured and developed since his unsuccessful first spell at the club ended seven years earlier.
Despite a bright start, Lukaku's form quickly dipped and he attracted the ire of Blues boss Thomas Tuchel following a fateful interview with Sky Italia.
In the interview, Lukaku spoke about how much he missed Inter, explained he was 'not happy' with his situation in west London, while he moaned Tuchel was not playing to his strengths.
He never recovered, and after eight league goals, Lukaku has spent the past two seasons on loan at Inter and Roma, all the while with two-and-a-half years still to run on his reported £325,000-a-week contract at Stamford Bridge.
Romelu Lukaku's return to Chelsea for £97.5m has failed to live up to expectations
Carlos Tevez - Boca Juniors to Shanghai Shenhua for £9m - 2016
Carlos Tevez's move to Shanghai Shenhua came right at the time of the ill-fated Chinese Super League boom.
While the £9m transfer fee didn't set tongues-wagging, the £630,000-a-week wages handed to Tevez certainly did, with the Argentine becoming the highest-paid player in the world.
It was hoped the striker would help his new side win the league for the first time, but instead Tevez scored just four goals in 20 games during his one season in China, working out at just over £8m per goal.
Carlos Tevez's stint as the world's highest-paid player in China at Shanghai Shenhua was awful
His fitness levels significantly dropped in China - where he was accused of being overweight - while he also seemed disinterested, and Tevez later described his stint there as a 'holiday'.
Shenhua fans didn't take to Tevez, booing him when he played, while they also dubbed him 'homesick boy'.
The Argentine took a parting shot at the club when going back to Boca as he said: 'They (Chinese players) are not as naturally skilled like South American or European players (and) even in 50 years, they still won't be able to compete'. A disaster all round.
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