The Premier League was founded in 1992 when the old First Division took the decision to break away from the English football league in order to capitalize upon a lucrative television rights deal. Since then, 46 different teams have played in the Premier League over 23 seasons. The wealthiest and most watched league in the world, the most recent television deal for the 2016-2019 seasons was worth $7.64 billion.
In the 23 years since its inception, some of the world’s finest players have graced the Premier League and some colossal transfer deals have taken place. Last summer, Premier League clubs parted with an estimated $1.4 billion over the transfer window, with a reported $170 million going to agents. Angel Di Maria is currently the most expensive Premier League import, costing Manchester United $88 million to prize the Argentine from Real Madrid.
Unsurprisingly, in over two decades of doing business, there have been some dreadful transfer deals in the Premier League. The criteria by which one defines a truly terrible signing is not exactly concrete, but one tends to equate the financial outlay committed by the team with the respective performances and abilities of the player. Further considerations include cost relative to the team and also the potentially detrimental effect the player had at the club once signing.
15 Bruno Cheyrou
Bruno Cheyrou had the unfortunate tag of being the "new Zidane" placed upon him by then manager Gerard Houlier, who signed him for Liverpool in 2002 for $7 million. Players described as the "next *insert name of world class player" very rarely live up to the status of the various aforementioned players, and so it proved with Cheyrou in relation to his compatriot Zidane. Following four successful years at Lille, including a goal against Manchester United in the Champions League, Cheyrou was hot property, and it was Liverpool who eventually secured his services. Despite struggling to ever find genuine form in England, Houlier persevered with his man. However, as soon as Houlier was replaced by Rafa Benitez, Cheyrou was loaned back to France, before eventually leaving the club on a permanent deal.
14 Jose Bosingwa
In all honesty, there is a whole host of recent QPR signings who could make this list, the likes of Shaun Wright-Philips, Anton Ferdinand, Djibril Cisse, Samba Diakite, Andy Johnson and Park Ji-Sung all proved very expensive mistakes, but Bosingwa wins it as the worst of a bad bunch. Bosingwa may have been a free agent when he joined QPR from Chelsea but he penned a three-year deal worth $96,000 a week. Upon his signing back in 2012, manager Mark Hughes claimed “He has a winning mentality,” it didn’t show. Bosingwa epitomised all that was wrong with that QPR team. Following a series of half-hearted performances he was fined two weeks wages for refusing to sit on the subs bench. Bosingwa sealed his fate as a terrible signing when he was seen to be laughing as he exited the field in the game in which QPR were relegated from the Premier League.
13 Steve Marlet
In 2001, newly-promoted Fulham FC spent a club record $17 million fee on French striker Steve Marlet. The extortionate price was never justified, as Marlet scored 11 goals in 54 games at Craven Cottage before being released and joining Wolfsburg on a free transfer four years after joining the club. Marlet's fee was deemed so excessive that Fulham's owner at the time, Mohammed Al Fayed, took Jean Tigana, who signed Marlet, to court. Al Fayed accused Tigana of paying an exorbitant fee for the Frenchman in order to take a cut of the deal himself, but the charges were eventually dropped.
12 Ali Dia
The name you will forever see crop up on lists of this kind, in the often divisive environment of football, there is general unity on the view that Ali Dia is the worst player to ever play in the Premier League, even though he only managed to play for 53 minutes. Graeme Souness signed Dia having never seen him play, following a recommendation made by Ballon d'Or winner George Weah to sign the Senegalese striker. Souness obliged and signed Dia on a one-month contract, the call turned out to be a hoax made by a friend of Dia's. He played just once for Southampton, coming on as a 32nd minute substitute before being subbed back off after 85 minutes, once Souness realized he could not in fact, play football.
11 Marco Boogers
Harry Redknapp signed Marco Boogers from Sparta Rotterdam back in 1995, for the considerable sum of $2 million. After a decade in the Netherlands, Boogers joined West Ham United despite the fact Redknapp had never seen his new striker play. In only his second outing for the Hammers as a second-half substitute Boogers was almost immediately sent off following a horror tackle on Gary Neville. The Sun newspaper then reported that Boogers had returned to Holland and was hiding in a caravan, although West Ham's PA has stated that was not the case. Either way, Boogers played only twice more, costing West Ham $500,000 per appearance as he played only four games for the Hammers before returning to Holland on a free transfer.
10 Andy Carroll
Some transfer fees appear extortionate and as terrible deals only with the benefit of hindsight, however, the transfer of Andy Carroll from Newcastle United to Liverpool for a fee in excess of $50 million was not one of them. There was shock among fans when the Reds parted with such a substantial fee for the target man. Carroll had enjoyed an impressive start to the 2010-11 season, although he'd played the previous campaign in the Championship. Carroll is undoubtedly a talented footballer, who is a nightmare for defenders when at his dominant best, but the eighth most expensive player in football? That is what he became in 2011, and he could never justify that price tag at Anfield, he scored 6 goals in 44 games before heading to West Ham for just over $20 million.
9 Bosko Balaban
Bosko Balaban cost Aston Villa over $9 million in 2001 when he signed from Dinamo Zagreb. It was hoped that the Croatian international would score the goals to fire Villa out of mid-table obscurity and into the midst of a battle for a European spot. He did not. He started two games for the club in a single season at Villa Park before being loaned back to Dinamo Zagreb, and eventually sold to Club Brugge. Balaban went on to score goals for almost every team he played for but his career did not work out in the Premier League, and at almost $5 million a start, he is surely one of the worst pieces of business in Premier League history.
8 Afonso Alves
When Middlesbrough signed Afonso Alves he had scored 45 goals in 39 games for former club Heerenveen in Holland, joining compatriots Romario and Ronaldo as the third Brazilian player to become the top scorer in the Netherlands, as well as just missing out on the European Golden Boot, finishing second to Francesco Totti. It is little surprise that there were high hopes over the $25 million man when he joined Boro in January 2008. His first season went okay as Alves notched six goals in 11 games but in his first full season the following year, he failed to live up to the lofty expectations and costly transfer fee that had been put upon him. He scored just four times in 31 games as Middlesbrough were relegated and Alves moved to Qatar in a $10 million move, as Boro lost $15 million on the striker in just 18 months.
You may notice a theme emerging here; buying a player having never watched them play is not a good idea. However, even the great Sir Alex Ferguson is not exempt from this error of judgement and in 2010 Manchester United parted with over $10 million to sign the 19-year-old. Bebe had only joined his current team five weeks earlier, on a free transfer, and hadn't made a single appearance for them, making the move seem a little bizarre to say the least. In four years at Old Trafford, Bebe played two games, before returning to Portugal.
6 Massimo Taibi
Sir Alex Ferguson has brought some of the finest players on the planet to Manchester United; Eric Cantona, Cristiano Ronaldo, Nemanja Vidic, Peter Schmeichel, the list goes on. However, when you spend 27 years at one club, even the most successful manager of all time is bound to pick up the odd dud, and Ferguson's second on this list and his worst signing was goalkeeper Massimo Taibi. The Italian shot-stopper signed for United in an $8 million deal from Venezia, and was tasked with replacing the formidable figure of Peter Schmeichel. Any goalkeeper would struggle to live up to such a task, although Taibi failed in spectacular fashion. A series of blunders, most notably against Southampton, saw Taibi quickly replaced. He played four times for the club before returning to Italy only a year later.
5 Andrea Silenzi
Andrea Silenzi was the first Italian to ever play in the Premier League, and quite possibly the worst. Silenzi signed for Nottingham Forest for $3.5 million and was handed a $80,000 a week contract, making him one of the best paid players around at the time. He made 20 appearances for Forest, only seven starts and failed to score a single league goal. The Italian striker was loaned back to Italy and when he refused to return from his loan deal, manager Mike Bassett tore up his contract, costing the club a reported $6 million, a truly terrible deal.
4 Jimmy Bullard
Jimmy Bullard signed for Hull City from Fulham in a deal worth around $7.5 million in January 2008. Flying in the league, the signing of Bullard seemed to signal the club's rapidly growing status in English football. However, although undoubtedly talented, Bullard's combination of ongoing injury troubles and off-field antics made him a dreadful signing for the Tigers. Bullard was injured in his debut and would not feature for the rest of the season. At times in his Hull career he showed what he was capable of on his day, but those occasions were all too infrequent. He only managed 23 appearances for the club before his $70,000 a week contract was ripped up for breach of club policy. Not only was Bullard a very expensive mistake for Hull City on the pitch, he also sullied the legacy of club legend Ian Ashbee off it.
3 Tomas Brolin
Most footballers suffer from inconsistency throughout their careers but few make it an art form in the spectacular fashion in which Tomas Brolin did. A rare creative force, Brolin made his name for Parma and the Swedish National Team. He won four trophies at Parma between 1992 and 1995, whilst being the joint top scorer at Euro '92 and making the World Cup All-Star team as Sweden finished third at the 1994 World Cup. In November 1995, Brolin signed for Leeds United for $9 million, the fact he was voted the second worst player to ever grace the Premier League in 2007 gives some measure of the decline of Brolin's career after joining Leeds. A tubby looking Brolin made 19 appearances for Leeds over two years before leaving the club, he could never revive his career and retired at the tender age of 28.
2 Savio Nsereko
It is difficult to understand quite why West Ham were willing to shell out $14 million for Savio Nsereko in 2009. The Ugandan-born winger had played a total of 23 games in his career and scored three goals prior to the move. His deal worked out as costing the Hammers $14 million per start, as he started only a single game for the club, with a further nine substitute appearances before departing only seven months after he had joined the club. Nsereko never looked like a $14 million player and has not since, he is currently plying his trade in Bulgaria for First Division side Beroe.
1 Winston Bogarde
Winston Bogarde has been back in the news over the last week as he gave his version of events on what happened during his time at Chelsea. A Dutch international, Bogarde boasted the likes of Ajax, AC Milan and Barcelona on his CV when he joined Chelsea in 2000. Weeks after signing, Claudio Ranieri became Chelsea manager and deemed Bogarde surplus to requirements. Having signed a four-year deal worth $80,000, Bogarde stated he was astonished Chelsea offered him such a lucrative deal and he wouldn't be able to get a similar contract anywhere else. Despite various attempts to out him, Bogarde stayed resolute, seeing out his contract and earning over $15 million in four years at Chelsea, playing just nine games. Bogarde once said "I may be one of the worst buys in Premiership history but I don't care," well, we agree Winston, and you top our list of the worst signings in Premier League history.