The 20 Worst Tottenham Hotspur Signings of the Premier League Era

Thomas CooperFeatured ColumnistNovember 13, 2013

The 20 Worst Tottenham Hotspur Signings of the Premier League Era

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    Danny Murphy had a tremendous career but didn't enjoy a particularly happy spell with Tottenham Hotspur.
    Danny Murphy had a tremendous career but didn't enjoy a particularly happy spell with Tottenham Hotspur.Mike Hewitt/Getty Images

    For worst Tottenham Hotspur signings of the Premier League era, you could also read most unfortunate or perhaps least successful.

    Much as critics of certain players like to diminish their contributions, only very few are genuinely bad.

    Mostly, if it does not work with a club, there have been reasons as to why the original transfer should, with hindsight, be regarded as a failure.

    Tottenham have made some terrific moves over the last 20 years or so (getting a World Cup star such as Jurgen Klinsmann, a top prospect such as Gareth Bale) and there have been some solid acquisitions, too (the likes of Scott Parker, Teemu Tainio and Mauricio Taricco).

    Along the way, though, there have been plenty more that did not work out as well as hoped. 

    Here follows (in roughly chronological order) 20 of these signings, each with a unique story as to why their respective time with Spurs will not be regarded as the happiest of their careers.

Ilie Dumitrescu

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    Romanian World Cup star Ilie Dumitrescu.
    Romanian World Cup star Ilie Dumitrescu.

    Along with Darren Anderton, Nicky Barmby, Jurgen Klinsmann and Teddy Sherringham, Ilie Dumitrescu was part of the "Famous Five" frontline Ossie Ardilies fielded to begin the 1994-95 campaign.

    Just like this adventurous system, the Romanian had a bright enough start, only to fall away when it became apparent things were not working as hoped.

    Dumitrescu and Klinsmann (and, soon after, Gheorghe Popescu) joined Spurs following the 1994 World Cup. Less of a known quantity than the German, he nonetheless came highly regarded.

    The winger's direct style was exciting but despite him scoring five times in the season's opening months, not always utilised for the good of the team. When Gerry Francis replaced Ardiles as manager, he decided to go in a different direction.

    After spending  time on loan at Sevilla, Dumitrescu briefly returned before joining West Ham United. Not for him was there to be the legendary status afforded his fellow summer arrival from USA '94.

John Scales

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    John Scales.
    John Scales.

    John Scales' injury-ravaged spell at White Hart Lane embodied a torrid time for Tottenham in the mid-'90s.

    Having proved himself as a steady, accomplished top-flight defender with Wimbledon and Liverpool, Scales should have been a smart bit of business from Gerry Francis.

    Instead, the occasional England representative was unable to replicate his contributions at those clubs during his three-and-a-bit years with Spurs.

    Scales was not helped by his team's descent into inconsistency and underachievement performance-wise. But in part, the absence of players such as himself—intended to be key members of the side—conspired to undermine Spurs here, too.

    A sad consequence of a frustrating period for the club. More injuries after he left North London ensured Scales' best footballing days had gone long ago.

Jose Dominguez

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    Jose Dominguez.
    Jose Dominguez.Graham Chadwick/Getty Images

    Someone for whom the term "luxury player" was created, Jose Dominguez had plenty of style, just not so much substance.

    As with several of the players in this article, Dominguez's fortunes were victim to tumultuous times at Tottenham. Two managerial changes made it hard for him to know whether he was coming or going amid different regimes.

    The Portuguese winger was phenomenally skillful, capable of summoning moments of brilliance that included a stunning long-range goal against Southampton in October 1997.

    Delightful as Dominguez could be, his passing and crossing were largely inconsistent, a product of a footballing brain for which moments of brilliance could not compensate for the areas he was lacking.

Paolo Tramezzani

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    Paolo Tramezzani.
    Paolo Tramezzani.

    Having worked hard to establish himself in Serie A, Paolo Tramezzani decided to try his luck in the English Premier League in 1998.

    The Italian was Tottenham's sole summer signing following the club's relegation near-miss the previous year. With Justin Edinburgh the only left-back in the squad, it was a move Christian Gross needed to make.

    Nonetheless, it was not one to get Spurs supporters too excited about.

    Unsurprisingly, things did not start well for Gross and he was soon sacked to be replaced by George Graham.

    Tramezzani had shown himself to be technically proficient early on in the campaign but would clearly need time to adjust to the ferociousness of the English game. With Gross gone and Graham less than convinced, an injury that autumn denied the player that chance and he quickly fell out of favour.

    With Ipswich Town's Mauricio Taricco brought in, Tramezzani was not long for North London.

Ben Thatcher

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    Ben Thatcher.
    Ben Thatcher.Shaun Botterill/Getty Images

    George Graham's desire to shore Tottenham up defensively saw him refashion several elements of the team he inherited.

    Steffen Freund was signed to provide tenacity in midfield, Mauricio Taricco bite and energy at full-back. Chris Perry proved to be a strong acquisition at centre-back while Neil Sullivan initially did well in goal.

    One recruit here who did not fare so well was Ben Thatcher.

    The left-back, like Perry and Sullivan, was well regarded off the back of his time at Wimbledon. The £5 million Spurs paid for him turned out to be far too much for a limited full-back.

    On his day, Thatcher's earnest, committed approach, coupled with decent production going forward, made him a solid player to have at left-back.

    Arguably though he was too eager, resulting in erratic performances and ill-discipline. After Graham was sacked, Glenn Hoddle instigated a different defensive approach that saw Thatcher soon sold off.

Milenko Acimovic

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    Milenko Acimovic.
    Milenko Acimovic.

    Milenko Acimovic's time at Tottenham was defined by a disastrous miss in a 1-1 home draw with Fulham in February 2003.

    If things had worked out well otherwise, it would not be cited so often in reminiscing over his time in the Premier League. Seeing as it did not, that miss has come to stand for Acimovic's failure to succeed.

    That is harsh because the Slovenian was a better footballer than that would suggest. The playmaker was a fine servant for his country and enjoyed good spells with Red Star Belgrade, Lille and finally Austria Vienna.

    At Spurs, though, beyond an occasional good display, he was never able to translate his talents. This was not helped by sporadic starting opportunities, but moments like that Fulham miss did not do his cause much good either.

    Had Glenn Hoddle not been sacked early in 2003-04, Acimovic might have earned the chance to rectify his slow start. Instead he was moved on to try his luck in France, not a part of the more pragmatic David Pleat's plans.

Kazuyuki Toda

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    Japanese midfielder Kazuyuki Toda.
    Japanese midfielder Kazuyuki Toda.Jamie McDonald/Getty Images

    With a good range of passing, Kazuyuki Toda was a player who, on paper, was well suited to Glenn Hoddle's aesthetically aspirational brand of football.

    Signed from Shimizu S-Pulse, the Japan international fleetingly showed signs of this in a few brief appearances in 2002-03.

    It became clear pretty quickly he was not suited to the comparatively battling nature of English football. Trying Toda was worth a shot, but this was a move that went down as a miss.

Jonathan Blondel

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    Jonathan Blondel.
    Jonathan Blondel.

    Another for the category of not suited to the English game, Jonathan Blondel had excelled in youth international football and was viewed as something of a transfer coup when Tottenham signed him in 2002.

    Perhaps the then 18-year-old was too a tad too young to be thrown almost headfirst into the Premier League.

    Regardless, despite clearly being a player with a good pass on him and the vision to make the most of it, in his few brief appearances for Spurs he struggled to contend with the combative necessities that come with life in a Premier League midfield.

    His absence from the current generation of Belgian stars currently representing their country so well suggests Blondel has found his level with Club Brugge in his home league.

Mbulelo Mabizela

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    South African defender Mbulelo Mabizela.
    South African defender Mbulelo Mabizela.

    Mbulelo Mabizela's one and only goal for Tottenham—a perfectly struck edge-of-the-box effort in a 2-1 win over Leicester City in October 2003—ranks among the finest seen from a Spurs player in the Premier League era.

    Sadly, it was to be the South African's only real moment of joy in England.

    Clearly talented, Mabizela's versatility allowed him to move between midfield and defence. The Leicester performance hinted at a quality performer at the making, yet the stars never quite aligned for him in North London in a way that would allow him to make the most of that potential.

    Glenn Hoddle had signed him but was gone before he had a chance properly to work with Mabizela. With Spurs in flux and looking to establish a modicum of stability, there was little opportunity to ease the homesick youngster into things.

    Mabizela would leave the next season, an unhappy spell in Norway contributing to a career that would end up with him back home, out of the limelight.

Helder Postiga and Bobby Zamora

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    Bobby Zamora.
    Bobby Zamora.

    One was an emerging striker fresh from success with FC Porto, the other a young forward who had made his name in English football with a goal-filled few years at Brighton & Hove Albion.

    Both Helder Postiga and Bobby Zamora came to Tottenham in the summer of 2003 with the intention of taking their respective careers to the next stage. Both had moved on by the beginning of the next season.

    The strikers had joined fellow new arrival Freddie Kanoute, as well as Robbie Keane, in a revamped Spurs attack. Glenn Hoddle was banking on the goals from his new, younger strikers taking his team forward in a way old hands Les Ferdinand and Teddy Sheringham would no longer be capable of.

    Ironically, Ferdinand and Sheringham (along with Steffen Iversen who had also left that year) scored on the opening weekend of the 2003-04 season, something neither Postiga or Zamora were able to do in Spurs' 1-0 defeat away at Birmingham City.

    Hoddle was ultimately right that those he let go were unlikely to do a whole lot more for Spurs. Unfortunately, neither Postiga or Zamora would either.

    It did not help when Hoddle was sacked early in the season. Each player's struggle for goals continued beyond August, and while briefly relieved (both grabbed a goal each in League Cup games, while Postiga scored in a league win over Liverpool), neither did enough to convince caretaker boss David Pleat to stick with them.

Stephane Dalmat

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    Stephane Dalmat.
    Stephane Dalmat.

    Stephane Dalmat takes his place on this list not because of a lack of quality, but the frustration at him conspiring to end a period with the club in 2003-04 that should have lasted longer than the few months it did.

    Joining on loan from Internazionale, he took a little time to find his feet in England. Once he had, his goal threat and thrilling ability to beat opposition players began to come to the fore in some sparkling displays.

    In a season of struggle for Spurs, on his best days Dalmat captured the imagination of supporters. His brace in a 4-1 win over Birmingham City particularly hinted at what he might do should he join the team in the long run.

    Yet there were a few too many bad days to make a deal viable. Particularly troublesome were off the pitch shenanigans which did not endear him to his teammates, notably a fight with the then 17-year-old Jamie O'Hara—as reported by the Sunday People at the time.

Andy Reid

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    Andy Reid.
    Andy Reid.

    Signed with Michael Dawson from Nottingham Forest in January 2005, Andy Reid was hailed as the greater coup in that £8 million combined deal.

    Dawson remains at Tottenham in 2013. Reid was gone within two years.

    Undoubtedly technically gifted, the Irishman never quite developed into a top-level player. Initially after joining Spurs, he performed well and notably scored a terrific long-range effort in a 5-1 win over Aston Villa.

    The following season his limited pace and combativeness were highlighted by the speed and toughness provided by Aaron Lennon and Edgar Davids respectively.

    Reid was good. It turned out just not good enough for the direction an upwards Spurs were heading in.

Grzegorz Rasiak

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    Grzegorz Rasiak.
    Grzegorz Rasiak.

    Grzegorz Rasiak's debut against Liverpool became the turning point for his brief Tottenham career.

    With a disallowed goal and a header that came off the woodwork, it was so nearly a goalscoring start for the transfer deadline day recruit from Derby County.

    Had he netted, the Polish striker might have been given more leeway than he was eventually granted by the Spurs supporters.

    Instead he looked out of his depth in the Premier League, his aerial threat not making up for a lack of quality on the ground. Compared to Jermain Defoe, Robbie Keane and Mido, Rasiak did not match.

    By February, he had moved back down a division to join Southampton.

Danny Murphy

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    Murphy celebrates a goal versus Portsmouth.
    Murphy celebrates a goal versus Portsmouth.

    In a year when the high-profile retirements of Sir Alex Ferguson and David Beckham have grabbed the headlines, Danny Murphy's recent decision to hang up his boots flew comparatively under the radar.

    Murphy had a career to be just as proud of, however. The classy midfielder was a tormentor of Ferguson's Manchester United for the best part of seven years in a successful spell with Liverpool. He was hugely influential, too, in Charlton Athletic and Fulham enjoying of their most successful periods in recent history.

    During his time at Charlton, Murphy was one of the Premier League's in-form midfielders. With this in mind, Martin Jol brought him to Tottenham as they attempted to qualify for the Champions League in 2005-06.

    Murphy's time in North London was the least successful of his top-flight career.

    His influence on younger teammates such as Michael Carrick and Jermaine Jenas was welcome, while Jol certainly was happy to call on him to come into the team. It was on one such occasion he scored in a 2-1 win over Portsmouth that helped kick-start Spurs' 2006-07 campaign.

    Understandably, infrequent appearances were not enough to satisfy Murphy. His was a luxury signing in that Spurs were better for having him as part of their squad but did not necessarily need him with others better suiting the balance of the team.

    Having been unable to usurp those in front of him in the Spurs midfield, Murphy made his way across London to the Cottagers in 2007.

Calum Davenport

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    Calum Davenport.
    Calum Davenport.

    Signed during then-sporting director Frank Arnesen's overhaul of the club's squad in 2004, Coventry City defender Calum Davenport was envisioned as a future Spurs stalwart.

    The then 21-year-old would take in loan spells with West Ham United, Southampton and Norwich City before he got his chance with his parent club at the back end of 2005-06.

    He would appear 19 times heading into the next season, benefiting from Ledley King's absence through injury.

    The 6'4" centre-back's physical attributes were sadly not matched by his footballing ones, though. Alongside Michael Dawson—still developing himself back then—they were too limited beyond defending their goal.

    Even there, Dawson was clearly the superior defender. With Anthony Gardner also around to deputise for King, Davenport was facing a battle for first-team football. He chose to try his luck with West Ham instead.

    Perhaps with time he might have proved his value to the squad. Given his failure to settle later in his football career (a situation that was admittedly made more difficult by personal troubles), hopes of Davenport becoming a Spurs mainstay were probably always going to be wide of the mark.

Kevin-Prince Boateng

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    Kevin-Prince Boateng.
    Kevin-Prince Boateng.

    One of the biggest wastes of talent in recent Tottenham history, since leaving North London in 2009, Kevin-Prince Boateng's form at Portsmouth, AC Milan and now Schalke has demonstrated what Spurs missed out on.

    Ahead of his current club's recent Champions League game with Chelsea, Boateng admitted—here via a Metro article by Massimo Marioni—that his immaturity had not helped matters.

    Still, he was not aided either by timing and situations that conspired to go against him.

    His first manager Martin Jol was gone within a few months of his own arrival. The Dutchman's replacement, Juande Ramos, handed him a run of appearances during that 2007-08 campaign but eventually decided he preferred others to the skilful Boateng.

    Ramos' apathy to the Ghanian was replicated by Harry Redknapp. Though the latter initially brought Boateng back in from the cold, he also soon decided the likes of Jermaine Jenas and Luka Modric were better suited to what he wanted.

    Underlining the whole sorry affair, Boateng came back to haunt Spurs when he scored Portsmouth's winner in their 2010 FA Cup semi-final.


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    Of the two Gilbertos to have played in North London, it is fair to say Tottenham did not get the better one. Gilberto Silva played his part in Arsenal's unbeaten season of 2003-04, as well as two FA Cup triumphs.

    Gilberto da Silva Melo scored a goal against Spurs' rivals West Ham and...that was just about it.

    In Heurelho Gomes, Sandro and Paulinho, Spurs have had better success with Brazilian recruits since the aforementioned left-back was in town between 2008 and 2009. Based on the latter, though, it would not have been surprising had they neglected to recruit from that part of South America again.

    In fairness to Gilberto, he joined midway through a season which Spurs were veering between the high of Carling Cup victory and mediocrity in the league. Settling in was hardly likely to be easy, and so it proved.

    Capped by 35 times by his country in a career that lasted the best part of 20 years, Gilberto was not a bad player. But he was clearly unprepared for the task of making it in the Premier League, fulfilling the bad and largely unfair stereotype that long surrounded the ability of Brazilians to acclimatise to the English game.

    (Honourable mentions for not-so-successful Brazilian signings go to Diego Bortolozzo and Rodrigo Defendi. Bortolozzo was on Spurs' books between 2002 and 2003 but never featured for the first team. Nor too did Defendi, an appropriately named defender signed in the Frank Arnesen era who also had unsuccessful loan spells with Udinese and Roma.)

Stipe Pletikosa

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    One-game wonder Stipe Pletikosa.
    One-game wonder Stipe Pletikosa.

    Tottenham's Croatian craze around the beginning of this decade reached its peak in 2010 when their national team's goalkeeper Stipe Pletikosa was signed on a season-long loan deal.

    Joining compatriots Vedran Corluka, Niko Kranjcar and Luka Modric, Pletikosa was signed as cover by Harry Redknapp for his first choice, Heurelho Gomes.

    Even with Carlo Cudicini still in the process of working his way back properly after suffering injuries in a motorcycle accident the previous year, it seemed a little perplexing to add another recognised goalkeeper.

    Pletikosa would state the following May that it had been "the wrong decision to come here"—via the Daily Mail.

    His only appearance came in a 4-1 League Cup defeat to Arsenal. While he served his purpose as back-up for Spurs, being third-choice keeper was a waste of international calibre talent.

Louis Saha

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    Louis Saha.
    Louis Saha.Mike Hewitt/Getty Images

    Louis Saha was by far the most baffling signing of Harry Redknapp's tenure as Tottenham manager.

    The Frenchman was brought in to strengthen Spurs' striking options in January 2012 after Roman Pavlyuchenko had been sold to Lokomotiv Moscow. Long past his best, Saha still had a goal in him, making him useful to have as back-up.

    Instead, Redknapp handed Saha the kind of game-time that he had not been willing to provide the superior Pavlyuchenko in his final season at Spurs. The Russian's replacement was lacking in movement and any real semblance of influence outside of the penalty box.

    Saha did grab a brace in the impressive 5-0 demolition of Newcastle United (his best performance) and scored as Spurs took the lead against Arsenal two weeks later. However, with his goal threat generally infrequent, it did not make up for his otherwise lack of effort.

    That hurt Spurs when they were attempting to defend their 2-0 lead in the North London derby. Saha listlessly watched on as the Gunners were allowed to build unchallenged from the back, eventually turning the pressure up and overwhelming Spurs in a humiliating 5-2 defeat.

    It beggared belief that Redknapp was choosing Saha ahead of Jermain Defoe so often, too. The latter had been largely playing understudy to Emmanuel Adebayor and Rafael van der Vaart, but when he had been called upon, he had responded with some strong showings.

    After such a strong first two-thirds to the 2011-12 season, Spurs lost costly momentum in their bid for a return to the Champions League late on. The unnecessary belief in Saha on Redknapp's part was one big reason.