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Manchester United had to work late into the night to finalise the signing of Monaco striker Radamel Falcao but eventually completed a season-long loan for the Colombian.
Despite details of the move emerging early in the day, United had to have an extension past the 11pm deadline to ensure the necessary documents were correctly filed with the Premier League.
They eventually announced Falcao's signing, which has an option to make the move permanent, at 1.30am, a deal which took United's summer spending past £150million.
By that time, Arsenal had confirmed United striker Danny Welbeck had joined them, for a reported fee of £16million, after Falcao's arrival made his chances of regular first-team football even more remote.
Show all 17 1 /17Manchester United's worst signings Manchester United's worst signings Luis Nani Perhaps harsh given some of the other names on this list, but Nani never lived up to the huge potential and talent he so clearly has. At his best he is up there with the very top players in the world, but the Portuguese winger, rather than replacing national team-mate Cristiano Ronaldo when he was sold, drifted into anonymity. He can dribble, cross and has a venomous shot with either foot, but Nani never scored more than 10 goals in a season and continued to frustrate Manchester United fans right until his last appearances for the club.
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Manchester United's worst signings Liam Miller Miller was supposed to be the next Roy Keane when he arrived at Old Trafford after a dominant breakout season at Celtic. But in two years at the club he managed just nine league appearances and was largely confined to playing in cup competitions. He left to Leeds and then Sunderland but never reached close to the level he was supposed to. Has spent the last four years plying his trade in Australia.
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Manchester United's worst signings Anderson Anderson looked brilliant in his first couple of years for the club, combining talent on the ball and the ability to drive a team on from midfield with a real bite and competitive desire in his play. He suffered from injury and then began to pack on the pounds - rumours of a party boy spirit certainly didn't endear him to Fergie. His excessive weight meant injuries became more frequent and when he got onto the pitch he was well below his best. Bought for £26m, left for free in January window.
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Manchester United's worst signings Gabriel Obertan Like David Bellion (more on him later), Obertan arrived as an extremely raw but extremely quick winger - the comparisons that he could be molded into Thierry Henry were inevitable. Obertan never had the talent required at Old Trafford and while his pace is always a threat, Obertan never worked out how to use it. Just three goals in five years in England for United and Newcastle is proof enough of that.
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Manchester United's worst signings Juan Sebastian Veron The most talented player on this list by a mile, Veron never settled in Manchester and was unable to adapt to the English style of play. Showed his quality in bursts, especially in some memorable Champions League performances, and had a good career after he left England, but the mammoth price tag (£28.1m in 2001) means he was an abject failure at the club.
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Manchester United's worst signings Massimo Taibi It was always going to be hard following Peter Schmeichel however not quite as hard as Taibi made it look. United paid £4.4m for him in 1999 which in the end worked out at just over £1m per first team appearance. Taibi had a disastrous opening four games for the club, flapping at a free kick on debut and allowing Sami Hyypia to score as well as conceding five against Chelsea and committing one of the worst goalkeeping blunders of all time as he allowed a tame Matt Le Tissier shot to roll straight through his legs - something he blamed on his spikes. They were to be his only four games for the Red Devils.
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Manchester United's worst signings Bebe Just a year after being homeless Bebe was inexplicably bought by Sir Alex Ferguson for £7m. He was said to be raw and one for the future, but in reality he was just bad. Appeared only seven times in red and looked completely out of his depth on every occasion - even though he managed to bag two goals. Somehow United managed to sell him to Benfica for only a small loss, after the Portuguese impressed during a loan spell in his native country.
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Manchester United's worst signings William Prunier Prunier had come through the Auxerre youth system with Eric Cantona however he did not share quite as an illustrious Man United career, managing just two first team appearances for the club. Ferguson brought him in on a trial with the intention of evaluating him in a few reserve team matches however he was hit with an injury crisis and Prunier was thrust into the first team. His club debut came against QPR where he was reasonably impressive however his second appearance did not go so well. United conceded four goals in a humiliating defeat by Tottenham and Prunier was singled-out for blame. He wasn't offered a permanent deal by Ferguson and returned to Europe.
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Manchester United's worst signings Pat McGibbon The Northern Irish defender was labelled as one of the stars of the youth team however he managed just one appearance for the club in what looked like an easy League Cup tie against York City in 1995. Unfortunately for McGibbon he was sent off and Manchester United crashed to a shock 3-0 defeat. He spent the next two seasons on loan before leaving for Wigan in 1997, still not having played a full 90 minutes for the club.
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Manchester United's worst signings Laurent Blanc Perhaps a controversial inclusion given that Blanc is a European Championship and World Cup winner and was voted the fourth best French footballer of all time; however Blanc was far from a success at Manchester United. Joining in 2001, as his illustrious career was drawing to a close, Blanc was signed to replace Jaap Stam but failed to fill the gap left by the big Dutchman's acrimonious departure. United finished the season third, their worst ever in the Premier League, and failed to win any trophy for the first time in four seasons. To blame Blanc entirely for this would be unfair but the Frenchman certainly did not enhance his reputation with his performances at Old Trafford.
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Manchester United's worst signings Jordi Cruyff Having a legendary father widely regarded as one of the best to play the game must be quite a hard act to follow, however Jordi did have the advantage of growing up and learning football in Barcelona and even broke into their squad while his father was manager. His United career was not successful, he failed to establish himself as a first team regular and made only 55 appearances in four years. Despite playing during one of the club's most successful periods he picked up only one winner's medal. He scored a paltry eight goals during his time at the club and eventually was shipped off to Alavés.
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Manchester United's worst signings Eric Djemba Djemba According to the chants the Cameroonian was 'so good they named him twice', unfortunately this proved to be painfully ironic for United fans as the midfielder signed as Roy Keane's heir failed to establish himself at the club. He managed only 20 league appearances for the club and within 18 months he was on his way to Aston Villa where he similarly failed to impress. Off the pitch he was known for his ridiculously excessive spending and reportedly had a fleet of ten 4x4 cars and 30 different bank accounts. By the age of 26 he was playing his football in Qatar.
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Manchester United's worst signings Kleberson Kleberson's performances at the 2002 World Cup led to his coach Phil Scolari declaring him the driving force behind Brazil's win and Ferguson signed him for £6.5m at the same time as Cristiano Ronaldo. However his career took a slightly different path to the Portuguese winger and the Brazilian, who had been signed as a replacement for the equally unsuccessful Juan Sebastian Veron, managed only 20 appearances for the Red Devils before being sold to Besiktas.
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Manchester United's worst signings Ralph Milne The man Ferguson himself labels as his worst ever signing despite only setting him back £170,000 is almost totally unheard of, largely because he failed to impress at United, contributing almost nothing on the pitch. In some ways he was the second coming of George Best unfortunately this was restricted to his activities off the pitch and Milne recently admitted he squandered most of his money on alcohol, women, and gambling. United was to be his last professional club in England.
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Manchester United's worst signings David Bellion The signature of Bellion was a controversial one with Ferguson allegedly tapping him up while still under contract at Sunderland. A £2m out-of-court settlement was reached but in the end Ferguson must have wished he hadn't bothered as the Frenchman scored only four goals in 24 appearances before eventually being shipped off to Nice having failed to establish himself as a first team regular.
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Manchester United's worst signings Diego Forlan There is no doubting Diego Forlan's class, the Uruguayan was the winner of the Golden Ball for the best player in the 2010 World Cup as he helped his team to a highly respectable fourth place and he scored an enormous amount of goals in the Spanish league for Villareal and Atletico Madrid before his move to Inter Milan this summer. However his time at United was not a success. It took him an incredible eight months and 29 games to score his first goal for the club and in his three years at Old TRafford he managed only 17 in 63 appearances. He even struggled with celebrating his goals - he took his shirt off after scoring against Southampton and was unable to put it back on in time for the restart. The arrival of Wayne Rooney coincided with his departure from the club.
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Manchester United's worst signings Dong Fangzhuo The first Chinese player to feature for United was signed in January 2004, however due to work permit restrictions he was unable to actually play for the Red Devils until 2006 and it wasn't until over three years after his signing that he made his debut for the club, at the end of the season, with the title already won. He made a substitute appearance in the Champions League and played an entire League Cup game as United lost to Coventry City but that was it. Dong failed to be given a squad number for the 2008-9 season with his number being given to Rafael da Silva and his contract was mutually terminated by the club so that he could find first team football elsewhere.
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And the presence of the Colombia international at the club's training complex late on Monday also spelled the end for Javier Hernandez, who earlier in the day joined Real Madrid on loan with a view to a permanent move.
United will pay Monaco between £5million and £6million for Falcao and will cover his wages, although they insist reports they will pay the 28-year-old almost £350,000 a week are wide of the mark.
Falcao was said to be desperate to leave Monaco (Getty Images) The delay on confirming a deal which had been in the pipeline all day sparked rumours Falcao had failed a medical on the serious knee injury which kept him out of the World Cup but United insisted throughout that was not true.
"I am delighted Radamel has joined us on loan this season," said manager Louis van Gaal.
"He is one of the most prolific goalscorers in the game.
Van Gaal will hope he can kick-start a stuttering beginning to the season which has seen United take just two points from three Premier League matches, scoring only two goals, without even taking into account their embarrassing Capital One Cup exit to League One MK Dons.
Van Gaal also needed reinforcements in defence after the loss of key personnel over the summer and they confirmed £14million Ajax defender Danny Blind had signed a four-year contract.
"Louis van Gaal is a tremendously talented coach, I have worked with him at Ajax and also for the Netherlands national team and I cannot wait to work with him at the biggest club in the world," the Holland international told manutd.com.
United's rebuilding has already seen them acquire midfielder Ander Herrera, defenders Luke Shaw and Marcos Rojo and British-record signing Angel di Maria.
Tom Cleverley looked to be moving to Aston Villa and then his preferred destination of Everton but the latter could not meet United's asking price.
However, United duo Nick Powell and Tom Lawrence both moved to Leicester on loan and permanent deals respectively while Michael Keane joined Burnley on a four-month temporary deal.
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