Red glum
Manchester United are renowned for growing their own, with the Class of '92 forming the foundation of their most successful period in club history. They've also been pretty savvy in the transfer market in the Premier League era, with Eric Cantona (£1.2m), Steve Bruce (£800k), Roy Keane (£3.75m) and Cristiano Ronaldo (£12.2m) particular highlights over the years.
They can't all be bargains, though, and as with every club there's a certain amount of wastage. It didn't take long for this lot's scarf-wielding smiles to disappear – 25 of the worst to pull on the United shirt...
William Prunier
Prunier only joined on trial at Manchester United, but saw his status quickly upgraded amid an injury crisis in late 1995. In just two games for the club the French defender made a name for himself... but not in a good way.
After a commendable outing against QPR, Prunier put in a shocking display as United lost 4-1 to Spurs on New Year’s Day 1996 – a performance which has gone down as one of the worst in Premier League history. Fergie did actually offer him the chance to extend his trial, but Prunier headed to Copenhagen instead.
Henrikh Mkhitaryan
Great things were expected of the Armenian when he arrived at Old Trafford from Borussia Dortmund for £30m as the Bundesliga Players’ Player of the Season.
However, he struggled to translate his German form into the Premier League and joined Arsenal just 18 months later. He didn't do much better there.
Matteo Darmian
The Italian defender joined Parma this summer after four seasons at United, making a combined 14 Premier League appearances in the previous two campaigns.
United forked out a reported £12.7m for his services but Darmian struggled to convince fans he was of the required standard before falling out of favour under Jose Mourinho.
Fred
The Brazilian is the only player on this list who still has the opportunity to put things right this season, but so far he's failed to suggest that a turnaround in fortunes is on the way.
United shelled out £52m to bring the midfielder in from Shakhtar Donetsk in summer 2018, but the 26-year-old’s performances have rarely impressed. He, like most of his team-mates, must up his game soon if he wants to work his way off this list.
Nick Powell
United moved swiftly to bring in promising teenager Powell from Crewe for £6 million after the 18-year-old showed signs of great potential in League Two.
Sir Alex Ferguson himself called Powell an “exceptional talent” after securing his services, but he failed to live up to his billing as a future star and appeared just nine times for the club before heading back to English football’s second tier, where he now plays for Stoke.
Victor Valdes
It’s impressive in itself that Valdes features on this list, given that he arrived on a free transfer with a glittering CV to his name after his time at Barcelona.
The Spaniard didn’t get along with United boss Louis van Gaal and made a total of two appearances for the club, until their Dutch boss announced that the goalkeeper would never play for him again after he'd refused to feature in an under-21 game.
Radamel Falcao
Yes, he was only a loan signing. But given the Colombian’s track record with the likes of Porto, Atletico Madrid and Monaco, and the fact that the Red Devils paid a £6 million fee to bring him in for a season, he proved to be a huge flop.
Falcao had only just returned from a serious knee injury when he got started at Old Trafford, and his struggles to return to full fitness were evident as he scored four goals in 29 games, leading United to politely decline the option to make his move permanent for £43.5 million.
Bastian Schweinsteiger
Louis van Gaal signed a winner in Schweinsteiger: eight Bundesliga titles, a Champions League, a World Cup, over 100 German caps. But when he switched from Munich to Manchester in summer 2015, Schweini was nearly 31 and clearly past his best; when Mourinho replaced Van Gaal a year later, the midfielder’s time was up.
The Portuguese coach wasted no time in letting everyone know how he felt about Schweinsteiger’s presence at United and sent him to train with the U23s, something the manager later admitted he could have handled better. Even so, by the end of March, Schweinsteiger had hopped across the pond to sign for MLS side Chicago Fire.
Mark Bosnich
“Mark Bosnich was a terrible professional,” wrote Sir Alex Ferguson in his autobiography. “We played down at Wimbledon and Bosnich was tucking into everything: sandwiches, soups, steaks. He was going through the menu.”
Bosnich – the only player Fergie signed twice for United – was far from a bad goalkeeper. Earmarked as Peter Schmiechel's successor, in 1999/2000 he played 23 league matches as United finished 18 points clear and became the first English side to win the Intercontinental Cup. But the following summer Fabien Barthez arrived, and within six months Bosnich was booted out again.
Gabriel Obertan
Obertan wasn't a big financial loss – indeed, a presumably delighted United recouped their £3m outlay when Newcastle gave him a five-year contract in 2011 – but he was a dead loss on the pitch: his 14 league appearances over two years included just four starts.
Even the man who sold him to Fergie, former Old Trafford centre-back Laurent Blanc, expressed dignified puzzlement: “I was surprised,” confessed Blanc. “They certainly hope to advance him, something that Bordeaux and Lorient have failed to do.”
Dong Fangzhuo
Dong arrived in Manchester as a 19-year-old, having barely kicked a ball in professional football. He cost the princely sum of £3.5m from hometown side Dalian Shide but was involved in just a single Premier League match during his four-year association with United – a drab 0-0 draw with Chelsea at Stamford Bridge in May 2007, with United having already secured the Premier League title and with both Ferguson and Mourinho fielding weakened teams ahead of the FA Cup final.
That solitary appearance came more than three years after he originally signed for the Red Devils due to work permit issues, and he was sold back to Dalian in 2008. His career petered out thereafter, with short spells in Poland and Armenia the highlights.
Wilfried Zaha
Palace winger Zaha was a man in demand this summer, now older and wiser after a difficult time at Manchester United.
Zaha was Alex Ferguson's leaving present for David Moyes: United paid £10m for him in January 2013, then let him stay at Selhurst Park on loan until the summer. He and Moyes made their debuts with a Community Shield win, but Zaha only made three more appearances before a January loan to Cardiff. He returned to Palace, the club he'd joined aged 12.
Zoran Tosic
Tosic joined United in the January transfer window in 2009 for a fee of around €7m but featured just twice before being loaned out to Bundesliga side FC Koln 12 months later. He had initially been expected to make the transfer from Belgrade giants Partizan with team-mate Adem Ljajic, but work permit issues meant that Ljajic’s move was delayed – and ultimately never happened, with United cancelling the deal before he arrived at Old Trafford.
Tosic is now back at Partizan following seven successful years at CSKA Moscow – and will face United in the 2019/20 Europa League group stage.
Diego Forlan
“He came from Uruguay, he made the Scousers cry”, warbled the United masses after Forlan scored a couple against Liverpool at Anfield in December 2002, helping his side towards the Premier League title. Sadly for the striker, that was about all he did in his two-and-a-half-years in England.
Signed in January 2002 for the best part of £7m, the (later) two-time European Golden Shoe winner failed to net in 18 appearances in his first campaign. Things improved the following season but Forlan didn’t reach double figures for goals in all competitions at Old Trafford and was moved on to Villarreal in summer 2004. There, he became the striker United hoped they’d bought three years before.
Kleberson
Summer 2003 was a strange time at Old Trafford. David Beckham left, as did Juan Seba Veron: beloved by Fergie but derided by most. In came David Bellion, Eric Djemba-Djemba, Tim Howard, Kleberson and a scrawny Madeiran kid called Cristiano Ronaldo.
In fairness to United’s scouts, Kleberson had been outstanding in his native Brazil, leading unfashionable Atletico Paranaense to their only national title in 2001 before playing five times in Brazil’s run to 2002 World Cup glory. In all, Kleberson played 32 times for his country, which is twice more than he managed in two seasons at United before being shunted to Turkish giants Besiktas in 2005.
Juan Sebastian Veron
Veron was unlucky to be the avatar of Fergie's initially unpopular decision to turn away from 4-4-2. He had won the UEFA Cup with Parma in 1999 then the Italian double with Lazio in 2000, but struggled to justify his £28m fee – then an English record – amid the hurried clatter of the Premier League.
Predictably he was better in the Champions League, but injury also took its toll and he was shuffled out to Chelsea (for £15m) after just two years. Before that, he inspired perhaps Fergie's angriest outburst, in a press conference full of journalists questioning Veron's worth: “I'm no' f*****g talking to you. He’s a f*****g great player, and youse are all f*****g idiots.”
Angel Di Maria
Di Maria signed for United in the summer of 2014 for the thick end of £60m, and was handed the hallowed No.7 shirt previously worn by the likes of David Beckham, Bryan Robson, Cristiano Ronaldo and Eric Cantona. Unfortunately for United supporters, Di Maria was more Neil Webb than George Best and left after just one season and 32 appearances in all competitions.
He's been largely excellent since joining PSG; much like Memphis Depay, Di Maria joined United at a difficult time, but the money paid compared to the impact he made means he makes this list comfortably.
Eric Djemba-Djemba
Upon signing Djemba-Djemba from Nantes in summer 2003 for £3.5m, Sir Alex Ferguson said the Cameroon international midfielder “looks like a United player in every sense”. Fergie got so much right during his 26 years but he couldn’t have been more wrong about the man signed to be the long-term replacement for Roy Keane.
Memphis Depay
Dutchman Depay was sensational for PSV before his move to Old Trafford in the summer of 2015 – and has been excellent since leaving for French side Lyon, too. So why didn’t he live up to his £25m transfer fee? He may have been the right player for the wrong manager... or rather, managers.
His compatriot Louis van Gaal was heavily criticised for a ‘boring’ style which wasn’t particularly conducive to accommodating players like Memphis, who isn’t known for his defensive contribution. Van Gaal tried him through the middle but Depay's opportunities were further limited after the appointment of Jose Mourinho in the summer of 2016: just four appearances later, he was sent to Lyon.
Massimo Taibi
As if losing Peter Schmeichel to Sporting wasn't bad enough, summer 1999 got even worse for the newly-ennobled Fergie when his first-team goalkeepers Mark Bosnich and Raimond van der Gouw picked up injuries. As the deadline loomed, the manager picked up Vicenza's Massimo Taibi for £4.5m. That would work out at more than a million quid per appearance.
Bebe
Let's just call the signing of Bebe a strange one all round. With a single third-tier season behind him, he’d only joined Vitoria de Guimaraes five weeks before his move to United was confirmed, with the Red Devils apparently signing him on the recommendation of assistant manager Carlos Quieroz.
But Quieroz has since denied ever having heard of the player before the move materialised, while Sir Alex Ferguson admitted Bebe was the only player he'd ever signed without watching him at all – even on video. Nobody seems to want to take responsibility; perhaps someone should ask Jorge Mendes, who became his agent days before the move.
Bebe played seven times for United in his first season, including twice in the Premier League, but never kicked a ball for the first team again. Although frequently loaned out, he remained on United's books until July 2014.
Alexis Sanchez
Surely, pound-for-pound, Manchester United's worst signing of all time? The Chilean spectacularly failed to replicate the form he showed at Arsenal after completing a move to Old Trafford in January 2018, before being dispatched on loan to Inter Milan this summer.
During a season-and-a-half with United, Sanchez scored just five goals in 45 games, earning a reported £500,000 per week in the process. We’re no mathematicians, but that ain’t value for money.
