Arsenal's 20 Greatest Transfer Window Signings

Tom Sunderland@@TomSunderland_Featured ColumnistJanuary 30, 2014

Arsenal's 20 Greatest Transfer Window Signings

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    As one of the most respected clubs among Europe's heavy hitters, Arsenal have remained a part of the continental elite thanks to some fine use of the transfer market over the last 30 years.

    Dating back to a time before Arsene Wenger reigned at the Emirates Stadium, a wealth of astute signings have been made by the North London outfit, helping them on the path to greatness.

    Here, we've ranked the 20 best investments ever made by the club, taking into account a number of criteria for each signing, including cost of the transfer, the context in which a move was made and the overall impact, and therefore value, that the player brought as a result.

    It's due to that last aspect, regarding value in retrospect, that some names have been left off the list, where obstacles may have blocked a player's way, regardless of how much the club's fans may adore said individual.

    For example, Tomas Rosicky's time at the Emirates has been blighted by injury, and despite the glimpses of quality and high expectations upon his arrival from Borussia Dortmund, the Czech veteran has been omitted as a result.

    However, the Gunners have had far more luck with their business in other instances, the best of which have been compiled for debate up ahead. 

    All appearances and goals statistics come courtesy of Arsenal's official club website.

Honourable Mentions

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    Nicolas Anelka

    Nicolas Anelka was seen as a major coup for Arsenal, signed from Paris Saint-Germain in 1997 as one of the most respected young talents in France; the then 17-year-old could have gone on to accomplish wonders in North London.

    But alas, it was not meant to be, and just two years after being acquired, the starlet was allowed to leave for Real Madrid, bringing in a profit in the region of £22 million. Scoring 28 goals in 90 appearances for Wenger's side, Anelka did have a swift impact with Arsenal, however.


    Theo Walcott

    Just failing to make the cut, Theo Walcott may yet find himself included on one of these lists in the years to come given his current trajectory, but he hasn't earned the right just yet.

    Signed in 2006 from the production line of talent down at Southampton, the speedster has since gone on to make more than 280 appearances for the club in total.

    That being said, that time hasn't come without its share of uncertainty, and the forward is only recently gaining prominence as a truly invaluable part of the starting XI.



    Something of an Emmanuel Eboue figure before Eboue was ever known to the Arsenal faithful, Lauren filled in as one of the most versatile and willing assets at the club's disposal during their Invincibles run.

    Able to fill in anywhere down the right flank as well as across the midfield and defence where needed, the Cameroonian will go down as one of the more unassuming heroes of the club during the early 2000s.


    Kolo Toure

    Kolo Toure came to the English top flight with no previous experience playing in Europe, acquired for a pittance from Ivorian side Asec Mimosas, but he stands as an example of the supreme scouting work that Arsenal are capable of.

    Swiftly, the malleable stalwart, capable in midfield or defence, became a staple of the team, and in only one of his seven seasons with the club, his maiden, did Toure make less than 40 appearances.

    Eventually sold to Manchester City for a big profit, Toure's no-nonsense mentality, largely from centre-back, eased the defensive needs of a side that was still recovering from some hefty departures in that area of the pitch at the time.

20. Emmanuel Adebayor

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    Transfer Fee: £3 million

    Fee Sold: £25 million

    Years Played: 2006-2009

    For more than a few, Emmanuel Adebayor will have been seen as the second coming of Nwankwo Kanu, resembling the former Gunners' fan favourite in appearance, attributes and playing style.

    However, it was a sign of the times when Manchester City came in with an offer that represented too good an opportunity for a profit for the club to pass on, Adebayor's name since becoming slightly less celebrated in North London.

    However, in terms of what the striker brought to the club during his three years there, especially considering he was a January purchase, the Gunners filled a necessary void with his scoring prowess.

    With 62 goals in 142 appearances, Adebayor was a savvy bit of business, even keeping one Robin van Persie guessing for playing time in periods.

19. Gael Clichy

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    Transfer Fee: Undisclosed

    Fee Sold: £7 million

    Years Played: 2003-2011

    One of the many French investments that Wenger opted for, Gael Clichy's eight years at Arsenal unfortunately coincided a little too closely with the beginning of the club's infamous trophy drought.

    However, a lack of silverware success, which was stopped with the FA Cup and Premier League double of the 2003-04 campaign, shouldn't obscure the individual worth that the former Cannes youngster brought to the side.

    After the sale of Ashley Cole, Clichy made for an easy transition at left-back from 2006, establishing himself as one of Europe's most consistent assets in the position for a time.

    The French international would follow Adebayor's example with a move to the Etihad Stadium in 2011, but his nominal transfer fee made Clichy's time as an Arsenal player all the more satisfying.

18. Mesut Ozil

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    Transfer Fee: £42.5 million

    Fee Sold: N/A

    Years Played: 2013-Present

    No matter how exciting his prospect may be, one can't pitch Mesut Ozil higher than a host of Gunners stalwarts after just five months in the squad.

    That being said, the well-known factor of the German breaking the club's previous transfer record almost three times over is one that sets him up for either a new era of success or one of the most tremendous falls in English transfer history.

    Thus far, his proficiency at the Emirates would appear to be pointing toward the former, and Ozil's £42.5 million acquisition is helping lay the path for what could be Arsenal's first title in a decade.

17. Nwankwo Kanu

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    Transfer Fee: £4 million

    Fee Sold: Free

    Years Played: 1999-2004

    Nwankwo Kanu will always be remembered for leading the Arsenal line during one of the club's most prolific title periods, albeit not always as the most prominent striker among their ranks.

    His 198 appearances for the club were almost equally split between starting places and bench appearances, but his 44 goals in that time speak for themselves.

    In five years with the club, Kanu won two Premier League trophies and two FA Cups, regarded by the fans as a favourite of theirs.

16. Gilberto Silva

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    Transfer Fee: £4.5 million

    Fee Sold: Undisclosed

    Years Played: 2002-2008

    Arsenal's unbeaten 2003-04 season was a feat that could only have been accomplished by a team of remarkable fortitude, an accomplishment not only of rare significance, but one that spoke so well of the outfit that collected it.

    However, any machine is a sum of its parts, and Gilberto Silva provided an anchoring presence in that setup that proved to be a critical component in pursuit of such an illustrious target.

    The Brazilian moved to North London in the wake of some magnificent performances in the World Cup that year; his six years under Wenger undoubtedly worth the £4.5 million fee paid for his services.

    By the time he departed the Emirates, Gilberto wasn't the same box-to-box presence as the one that arrived, but in a team that often boasted a thriving number of young stars, the veteran was always a calming presence—even if his sometimes aggressive style of play didn't indicate it as often.

15. Emmanuel Petit

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    Transfer Fee: £2.5 million

    Fee Sold: £7 million

    Years Played: 1997-2000

    Arsene Wenger had a major hand in bringing Emmanuel Petit to Monaco during his time on the French Riviera, and maintained his interest in the 1998 World Cup winner by drafting his talents to Highbury, too.

    The blond bombshell was one of numerous talents who saw their skill sets changed under the French tactician, his roots as a centre-back being transformed, albeit gradually, into becoming one of Europe's most revered midfield anchors. 

    He played in the Premier League for just three years before a move to Barcelona came calling in 2000, where he was responsible for £7 million of the £32 million double deal that saw both him and Marc Overmars head to the Camp Nou.

14. Sylvain Wiltord

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    Transfer Fee: £13 million

    Fee Sold: Free

    Years Played: 2000-2004

    Sylvain Wiltord was a part of the thriving French contingent that emerged at Arsenal following the successful 1998 World Cup and Euro 2000 tournaments.

    His initial four-year contract was never renewed, but 175 appearances for the club came as a crucial part of Wenger's squad, in which the forward was a very reliable option both from the bench and in the starting XI.

    Among Wiltord's 49 goals for Arsenal was the finish at Old Trafford that would sew up the North Londoners' double in 2002, writing his name into fan folklore and establishing himself as an Emirates fan favourite.

13. Marc Overmars

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    Transfer Fee: £6 million

    Fee Sold: £25 million

    Years Played: 1997-2000

    An example of the highly fruitful relationship that Arsenal have held with Dutch football down the years, Marc Overmars is another example of a player whose impact in the Premier League could have been so much more were it not for Arsenal's sensible transfer model.

    Having starred in the Ajax squad for five years, the Gunners leaped at the opportunity to bring the winger in for what would arguably become his best years with an elite European club, Barcelona being the other candidates for that award.

    Signed in Wenger's first full season at Highbury, the speedster shrugged off any injury concerns that once blighted his development and would win the double to reward the manager's faith in his ability.

    A relatively expensive risk at the time, it was the prolific nature in which Overmars went about his business in England that sees him so high up the list, his 41 goals in 142 games for the club being a very good return for one in his circumstances.

12. Freddie Ljungberg

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    Transfer Fee: £3 million

    Fee Sold: £3 million

    Years Played: 1998-2007

    Signed from Halmstads for what was then the highest fee ever paid for a Swedish player (£3 million), Freddie Ljungberg's success may have been a pleasing surprise for many at Arsenal.

    His talents as a midfielder will have been unknown to some prior to his arrival, but over the next nine years, the Gunners would go on to get more than their value for the man, who has since been named one of the club's 50 greatest players ever.

    More than 300 Arsenal appearances to his name and just short of a decade with the club, Wenger's side would go on to get their initial outlay back from West Ham. Although his time at Upton Park would seek to besmirch Ljungberg's good name, the playmaker retains his spot as one of the Emirates Stadium's prodigal sons.

11. Cesc Fabregas

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    Transfer Fee: Free

    Fee Sold: £35 million

    Years Played: 2003-2011

    Wenger might be looked upon as the pioneer of how to buy talent young from abroad before nurturing it in one's own yard, and it's thanks to players like Cesc Fabregas that the policy has stood the test of time.

    Arriving in the shape of an inconspicuous 16-year-old from Barcelona, it didn't take Fabregas too long before he started to make his moves into the first team.

    Like so many others, the playmaker's journey at Arsenal would end with a seemingly better opportunity presenting itself, this time with a return to boyhood club Barca, but there were plenty of positives worthy of note during the midfielder's run at the Emirates.

    Fabregas will be regarded as perhaps the most devastating sufferer from the Gunners' trophy-less years, his involvement in the 2005 FA Cup win followed up by a barren run where he served as a leading figure despite hard times befalling the club.

10. Robin Van Persie

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    Transfer Fee: £2.75 million

    Fee Sold: £22.5 million

    Years Played: 2004-2012

    Though some fans will dispute his status after moving to Premier League rivals Manchester United, Robin van Persie nonetheless remains one of Arsene Wenger's best investments of the current century.

    That being said, the Dutchman did take his time into developing into the striker we all know today.

    A mixture of injuries and lacking form meant that in only three of his eight seasons in North London did the attacker manage to make 40 appearances or more.

    Most recent Arsenal memory will see van Persie as the figure who finished the 2011-12 Premier League campaign as the Golden Boot winner and almost the sole reason behind any of the Gunners' success that year, helping to keep their record of Champions League qualification running.

    In total, 67 of the forward's 279 appearances for the club came from the bench, but van Persie's eventual maturing into one of the world's most reliable finishers is perhaps the finest example of Wenger's eye for a talent, and his perseverance in waiting for those diamonds to be unearthed.

9. Sol Campbell

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    Transfer Fee: Free

    Fee Sold: Free

    Years Played: 2001-2006, 2010

    Probably the best player ever to have dared featuring for both North London clubs in his career, Sol Campbell's career at Arsenal mainly differed in trophy count compared to his White Hart Lane tenure.

    However, the centre-back's quality remained consistent, and it was during his time with Wenger that the Englishman established himself as one of the toughest central defenders of his time.

    The fact that Campbell didn't cost Arsenal a penny in transfer fees only makes his success at Highbury all that much sweeter, and his short second stint with the club in 2010 was a nostalgic send-off for the veteran, although not a heavily involved one.

    Two Premier League titles and three FA Cup crowns all point to a player that served as part of arguably Arsenal's greatest line-up in history, his transfer value not eclipsed by many through the years.

8. Robert Pires

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    Transfer Fee: £6 million

    Fee Sold: Free

    Years Played: 2000-2006

    With fans still reeling from the departure of Overmars the previous summer, Robert Pires helped ease a blow which otherwise threatened to dismantle a free-flowing and engaging Arsenal attack.

    As it would be, the Frenchman's impact at Highbury was greater than what the Dutchman accomplished with the club, his influence in the creative channels being one of the main driving forces behind one of England's most celebrated offensive link-ups ever.

    Things didn't begin easily for Pires, but by the time he moved on to Villarreal as a free transfer in 2006, he had proven himself as a favoured son of the Premier League.

    In 284 appearances for the Gunners, the 1998 World Cup winner scored 84 goals and bonded most comfortably with a certain pair who would craft something unique together.

    But more on those two later.

7. Nigel Winterburn

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    Transfer Fee: £350,000

    Fee Sold: £250,000

    Years Played: 1987-2000

    It's a glamorous list to contend with, but one might argue that Nigel Winterburn is the best left-back ever to have played for Arsenal, coming from Wimbledon in 1987 for what's now looked upon as a pittance at £350,000.

    Wimbledon may have laid the foundations for Winterburn's top-flight career, but 584 appearances for the Gunners tell us that it was Arsenal who got the best out of the player, and what a career it was after 13 years at Highbury.

    It actually took the full-back a season to make his break into what would go on to become known simply as "The Back Four," but there was no budging the left-sided figure once the position was his.

    Providing a well-rounded figure at left-back, adept both in contributing to the attack and the more defensive priorities, Winterburn left for West Ham at the age of 36, with three league titles, two FA Cups, a League Cup and a UEFA Cup Winners' Cup in tow.

6. Lee Dixon

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    Transfer Fee: £375,000

    Fee Sold: Retired at club

    Years Played: 1988-2002

    Fifteen years at any club is impressive; 15 years at a club of Arsenal's calibre is nothing short of outstanding.

    But such was the concrete stability that Lee Dixon brought to the Gunners' back four, the club couldn't afford to let his presence leave their fraternity, and he was by no means looking to leave it.

    Having plodded along at Burnley, Bury, Chester City and Stoke City before his time in North London, it was a magnificent stepping up to the fore from Dixon, whom some might not have expected to respond to the challenge in such an astute manner.

    Up until a knee injury would affect his trademark positional skills toward the end of his career, the Manchester native did away with the challenges of several would-be hopefuls for the Arsenal back line, eventually calling it a day with his reputation intact, to say the least.

5. David Seaman

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    Transfer Fee: £1.3 million

    Fee Sold: Free

    Years Played: 1990-2003

    All of David Seaman's 564 appearances for Arsenal came as part of the starting XI which, while not totally uncommon for goalkeepers, still adds a nicely rounded touch to the goalkeeper's reign.

    The ponytail-sporting stalwart was replacing a fan favourite at Arsenal in the form of John Lukic. The fans were sad to see their previous No. 1 leave at the time, but such allegiances didn't take too long to switch.

    In a 13-year career at the North London side, Seaman won the First Division and Premier League titles on three occasions, along with four FA Cup victories, a League Cup and a UEFA Cup Winners' Cup to go with them.

    Though his England career wasn't always of the same, consistent quality, Seaman often proved his worth over an entire campaign.

    It was in his last season with the club that his celebrated save against Sheffield United in the semi-finals of the 2002-03 FA Cup came, a moment that contributes to the most revered goalkeeper's tale in Arsenal history, but doesn't even begin to tell his story.

4. Ian Wright

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    Transfer Fee: £2.5 million

    Fee Sold: £500,000

    Years Played: 1991-1998

    The second-highest goalscorer in Arsenal's history, no striker of the 1990s was loved more in North London, and for some perhaps even England, than Ian "Wright Wright Wright."

    With 185 goals in 288 appearances for the Gunners, Wright exploded onto the scene at Arsenal having already impressed at Crystal Palace, and he has always been seen as one of the most adored and enthusiastic personas in the club's lore.

    The forward finished every one of his seven seasons with the club in double-scoring digits before heading to Upton Park for his career swan song.

    The moment when he broke Cliff Bastin's record of 178 goals to become the club's all-time leading scorer in September, 1997, will always be remembered within the Emirates' hallowed halls, showing that while venues may come and go, a club's history can never be erased, nor that of an individual.

    As for the player who holds the current scoring title, that's still to come.

3. Patrick Vieira

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    Transfer Fee: £3.5 million

    Fee Sold: £13 million

    Years Played: 1996-2005

    When the word "leader" is mentioned around the Emirates Stadium, most minds will immediately be cast toward the figure of Arsenal's captain supreme, Patrick Vieira.

    Having failed to make the impact expected of him with Milan, it was the news that Wenger would soon be replacing Bruce Rioch as boss that apparently swung Arsenal into the favoured position ever to land the French international, and neither party ever looked back.

    In a nine-year tenure as a Gunner, Vieira helped in reshaping the club and their expectations, shielding one of the best defensive line-ups that England could boast at the time, distributing to some of the best weapons the nation had ever seen in kind.

    The midfielder's skill set was perfectly fitted to Premier League football, and a no-nonsense mind set coupled with superb control and playmaking made for one extremely dangerous resource in the middle of the park.

    Terms with Inter, Juventus and Manchester City would follow in the years after his 2006 Arsenal exit, but Vieira will always be most revered for what was accomplished in his time alongside Wenger, three Premier League winners' medals and four FA Cups merely some of the material testaments of something much deeper.

2. Dennis Bergkamp

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    Transfer Fee: £7.5 million

    Fee Sold: Retired at club

    Years Played: 1995-2006

    Dennis Bergkamp is completely deserving of the term "legend" being attributed to his name as a result of his 11-year run at Arsenal, with no player since producing the same vision that the Dutchman had for spotting weakness.

    Having allowed Inter to take him from Amsterdam initially, Bergkamp was actually a very expensive outlay for the Gunners at £7.5 million, but he was worth every bit of the investment and then some.

    Now passing his knowledge onto the stars of tomorrow at Ajax, the 44-year-old lit up Highbury, not always through his own direct impact, but often through another vessel, whom he had opened space up for and so graciously handed a scoring opportunity to.

    Wenger picked up where Rioch left off when it came to Bergkamp's development, and it was under the Frenchman that the player enjoyed the best seasons of his career.

    Bergkamp perfected his supporting attack role to a tee, scoring 120 goals in 423 outings for the North London side, writing his name into the history books thanks to more than a decade of producing at the very elite standard.

1. Thierry Henry

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    Transfer Fee: £11 million

    Fee Sold: £20 million

    Years Played: 1999-2007, 2012

    It's not every day that a player is immortalised in statue form by a club, but when you've got it, you've got it; Thierry Henry had it.

    Having failed to adapt to life in Italy, Arsenal swiftly stepped in with a sum that repaid Juventus in full for their failed investment, Wenger making the most of a bad situation, so to speak.

    That is, of course, if you call "making the most" of something signing a player who had tailed off in form before turning him into one of the most devastating forwards football has ever seen, who to this day remains Arsenal's leading goalscorer.

    For after 377 appearances for the Gunners across two separate spells, Henry netted 228 times for the Premier League giants, and it's the New York Red Bulls now benefiting from that same presence.

    Whether it was a chance fashioned out of his own ingenuity or simply the finishing touch on what a team-mate had engineered, the Frenchman was always relied upon to make something positive happen with the ball at his feet.

    For good reason, too, with the former Monaco man eclipsing anything that any Arsenal attacker ever accomplished or has accomplished since.

    Big outlay or small, for what Henry has contributed to the club, his value is indeterminable.