West Ham United have never been a club renowned for making astute purchases in the transfer market.
Instead, the Hammers have historically promoted promising youngsters from their fabled ‘Academy of Football’ and thrusting them into the spotlight of first team football.
Naturally, this attracts the attention of bigger clubs and thus begins a vicious cycle which stopped the east Londoners from progressing.
Although this has changed somewhat in recent years, West Ham have been tantalisingly close to pulling off exceptional transfers over the years which could have finally propelled them from the doldrums of mediocrity.
Sam Allardyce revealed on the Alan Brazil Sports Breakfast he nearly signed Jamie Vardy during his stint as manager, but could not justify splashing out £1million on a player from the Conference.
Vardy would of course go on to sign for Leicester City, win the Premier League title, play for England at two major tournaments and score more Premier League goals than Cristiano Ronaldo.
Meanwhile, Big Sam was left to rue his hesitancy as he instead plumped for John Carew and Sam Baldock in the summer transfer window of 2011 – with neither player lasting longer than one season.
Unfortunately for Hammers fans, it seems this is not an isolated incident as the club have been linked with (and failed to sign) some of the biggest names in football in the past two decades.
Indeed, it seems fortunes are always hiding in the East End, as this list below suggests.
We count down the 10 biggest names, in no particular order, that West Ham failed to sign and reveal who they signed instead.
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During his time at Galatasaray, the powerful Ivory Coast international revealed he could have joined West Ham United before he moved to Chelsea in 2004.
In fact, way before Jose Mourinho brought him to Stamford Bridge, Drogba was scoring goals for fun at Guingamp and an offer came in from West Ham in 2002.
“I was at Guingamp at that time,” Drogba told Sky Sports News. “I’d just arrived at the club and they came to my house and spoke, but it didn’t happen. I wasn’t ready to go.”
The Hammers decided to stick with Paolo Di Canio and Frederic Kanoute up front, signing Les Ferdinand as an experienced deputy striker and Youssef Sofiane as one for the future.
But injuries to Kanoute and Di Canio left the Hammers woefully short up front and they were subsequently relegated in the 2002/03 season with a record 42 points.
Juan Roman Riquelme
After completing the takeover of their boyhood club in January 2010, David Gold and David Sullivan set about transforming the club from relegation contenders to European heavyweights.
Following a disastrous January window (more on that later) the Hammers decided to flex their newfound financial muscles and made an ambitious move for Riquelme.
The former Argentina and Barcelona midfielder was out of contract that summer having left boyhood club Boca Juniors and moving to the East End was said to be ‘the best option’, according to the 31-year-old’s agent.
However, the midfielder opted to re-sign with his beloved Boca and Avram Grant brought in Thomas Hitzlsberger to play alongside Scott Parker and Mark Noble.
The Germany international almost instantly picked up an injury and did not make his debut until 2011, leaving supporters craving the sort of football hedonism Riquleme could have brought.
A star in his native France, Loic Remy seemed destined to pull on the famous Claret and Blue on more than one occasion.
However, the striker rejected the club on several occasions and the alternative options were just not able to cut it at the top level.
In 2010, rumours began to swirl suggesting David Sullivan was keen to fly the 23-year-old from Nice in order to beat Liverpool to his signature in a deal worth £14.3m. However, this was never substantiated and it appears as though they were closer to a deal later on in his career.
In the January window of 2013, the club were keen to bolster their striking options after an injury to summer signing Andy Carroll. Remy seemed destined to move from Marseille, but QPR stumped up the necessary catch to bring him across London to Loftus Road.
In a desperate move, the Hammers signed Marouane Chamakh on loan from Arsenal, who proceeded to score exactly zero goals from his three appearances.
Long before the skull cap or the Europa League failure in Baku, Cech was considered to be the hottest prospect in world football.
Although Sir Alex Ferguson claims he nearly signed the 6ft 5ins shot-stopper for Manchester United, it seems as though the Hammers could have had the Czech Republic No.1 between the sticks.
Cult hero Ludek Miklosko spotted his compatriot’s talents in the summer of 2002, but decided he should stay in his native country to continue his development.
“I was interested in bringing Petr over to England when he was 19, but I eventually decided that it would be a mistake,” he told the Evening Standard. “He was not yet ready for English football and needed to continue his development back in the Czech Republic.”
While Cech spent two years at Rennes before his move to the Blues, Glenn Roeder plumped for the experienced signing of Raimond van der Gouw from Man United instead.
Ruud van Nistelrooy
Although we briefly mentioned the disastrous 2010 January window for the Hammers previously, it would feel wrong to not be more strenuous in our assessment.
Fresh after saving the club from administration, Gold and Sullivan actively pursued a prolific striker to help lift Gianfranco Zola’s side away from the relegation places.
Real Madrid striker Van Nistelrooy was identified as the man to help save the Hammers from the drop, with Los Blancos ready to sell having signed Karim Benzema in the summer of 2009.
In fact, West Ham were reportedly willing to spend up to £100,000-a-week on the veteran striker. However, the Netherlands international opted to join Hamburg instead in the Bundesliga.
Zola convinced the board to bring in three strikers instead; Mido, Ilan and Benni McCarthy. Safe to say all three were less than successful.
In 2009, West Ham lost Craig Bellamy to newly minted Manchester City and were in desperate need of a strike partner for Carlton Cole.
The Daily Telegraph reported Uruguay international Cavani was top of the summer wishlist after his breakthrough season at Palermo where he scored 15 Serie A goals.
However, the Italian giants were only open to a deal at the end of the following season so as to not leave them high and dry in the middle of the campaign.
West Ham were not willing to wait and brought in Luis Jimenez on loan from Inter Milan, in order to supplement Savio Nsereko who had signed immediately after Bellamy’s departure.
Ultimately, Napoli coughed up €17million at the end of the 2009/10 season to get ‘El Matador’, while Jimenez returned to the San Siro after his ineffectual season.
After a successful first season in the Premier League, Sam Allardyce wanted to push the club onto the next level and set about securing the permanent transfer of Andy Carroll.
After a successful second half of the 2012/13 season, it made sense for the Liverpool striker to leave Anfield for good as the relationship between Luis Suarez and Daniel Sturridge began to blossom.
But the Reds decided to play hardball for the England striker, much to the chagrin of Big Sam.
He instead made a £14.5m move for Sevilla striker Negredo, with the Spain international playing a part in La Roja securing Euro 2012. Carroll then became available and it mattered little that Sevilla wanted a far larger fee for their striker.
Negredo instead moved to Manchester City where he scored 23 goals in his first season, including a hat-trick in the League Cup semi-finals against the Hammers. Carroll moved to West Ham for £15m and proceeded to score 23 goals over the course of the next four seasons COMBINED.
The Frenchman’s rise from the lower leagues of French football to the World Cup in the space of four years is quite remarkable, but it could have all been so different.
Former West Ham boss Slaven Bilic confirmed the club were interested in signing the holding midfielder from Caen in the summer of 2015, before his £5.6m move to Leicester City.
“He was on our list, we were quite close, quite close,” Bilic revealed. “I had watched him in France. He was a good player, the same player he is now at Leicester – a holding midfielder, not very tall but he is one of those players that after 20 minutes you think there are twins.
He added: “He was on our list, but then we got some other players for the same position and it was a bit too many players for the same position.”
Kante went on to lead the Foxes to the Premier League title, while the Hammers scraped through to the Europa League with Alex Song and Pedro Obiang at the base of their midfield.
As mentioned at the start, West Ham have made a habit of providing academy graduates with the opportunity to flourish in the first team.
However, they tend to be supplemented by more senior pros in order to further their development, much like Di Canio did with Jermain Defoe.
Michael Carrick emerged from the academy at around the same time as Guardiola’s contract expired at Barcelona in the summer of 2001.
But manager Roeder decided to stick with Carrick at the base of his midfield, bringing the attack-minded Don Hutchinson to play alongside him at Upton Park.
Guardiola moved to Brescia instead on a loan deal, before joining Roma in 2002.
Yes, you have read that heading correctly, West Ham United were once seriously linked with a move for the world’s most expensive player.
In 2010, Avram Grant lined up a club-record £16m bid for ‘the new Pele’ as Santos braced themselves for bids from across the globe for the 18-year-old forward.
Although the likes of Real Madrid were seriously interested, a move to Upton Park was considered appealing as it could thrust the forward into the sights of some of the bigger Premier League clubs, like Chelsea.
However, Neymar’s father (who also is his agent) decided he did not want his son to move too early in his career and decided to wait until a club met Santos’ £28.4m release clause.
Deterred, West Ham signed Victor Obinna on loan from Inter Milan. The Nigeria international showed flashes of class, but not enough to stop the club slipping into the Championship.