The transfers that got away

Every club has countless tales of highs and lows, but few can match Tottenham Hotspur in terms of Transfer Window drama. Many Tottenham fans have been subjected to more emotionally taxing transfer windows in the past 10 years than the average straight-thinking football fan should have in a lifetime.

For every one great move for a Rafael van der Vaart or a Hugo Lloris, there are countless other potential deals that were dashed after hopes had been raised. Tottenham have seen more falls at the final hurdle than a wet day at the races and with Cheltenham coming up, I want to use this article to have a quick look at some of the ones that got away…

Joao Moutinho

First linked to Spurs: 2012
Where is he now? AS Monaco

Minutes. That was the difference. Minutes

In the late hours of the Summer 2012 transfer window, Andre Villas-Boas wanted to stamp his own mark on the Tottenham team. With Luka Modric gone to Real Madrid, and van der Vaart moved on to Hamburg, Tottenham’s midfield was bereft of creativity and AVB turned to his countryman Joao Moutinho to provide the solution.

Spurs fans rightly mourned the loss of their two prestigious playmakers but Moutinho seemed the perfect candidate to replace them. Having excelled for Porto and Portugal in the same deep-lying playmaker role that Modric enjoyed in Tottenham, the then 25-year old seemed destined to prosper at White Hart Lane.

However, as is often the case with these tales, the transfer fee became the sticking point. Despite having raked in over £50million from the sales of Modric, van der Vaart and Niko Krancjar among others, Daniel Levy refused to pay over the odds for the Portuguese maestro. In the end, Levy’s hard-nosed negotiations seemed to be a stroke of genius as Sky Sports announced that a £22million fee had been agreed just before the transfer deadline shut. Unfortunately, all the haggling meant there was insufficient time left to push through the mandatory paperwork, and the hopes of completing the Moutinho move vanished. Hopes of a deal at a later stage were dashed in May the following year, when AS Monaco splashed out €70million to Porto for a double deal including Joao Moutinho and his teammate James Rodriguez.

Tottenham have since rebuilt and the current midfield looks as healthy as it’s been in a decade, but what about Moutinho himself? His club career at Monaco has been modest at best, where they are perennial second-fiddle to PSG in Ligue Un. On the international stage though, Moutinho was an essential cog in the Portugal team that achieved EURO glory in the 2016 European championship.

Klaas-Jan Huntelaar

First linked: 2008
Where is he now? Schalke

Klaas-Jan Huntelaar is probably a name many Tottenham fans relate to even more than a some of the strikers who have actually played for the club.

In 2008, KJH was the latest shiney new striker to come out of the Ajax system. After being the leading scorer in the Euro u21 Championship in 2006, and leading the scoring charts in the Eredivisie in 2006 and 2008, comparisons the the likes of Ruud van Nistelrooy, and links to big clubs inevitably followed.

Tottenham were one of many clubs said to be interested, and fans were excited at the prospect of seeing the young Dutchman link up with fellow new signing Roman Pavluychenko. Alas, In Decemeber 2008, Spanish giants Real Madrid agreed a deal of €20million to take Huntelaar to the Bernabeu. However, Huntelaar’s time at Madrid wasn’t as successful as either party had hoped. In the following summer, after just half a season, rumour of a move surfaced, and Tottenham again were linked to the striker. As the likes of Man United cooled their interest, it seemed a move to Tottenham was imminent, until AC Milan swooped at the last second to sign the striker in August 2009.

Just a year later, KJH packed his bags again, and moved on to Schalke in Germany, where he finally seemed to settle. Between 2010 and 2014, The Dutchman hit 91 goals in 139 games, and as Spurs hierarchy began to lose faith in Roberto Soldado, the link Tottenham Hotspur surfaced once more. In summer 2014, Spurs were chasing fellow dutchman Michel Vorm when the KJH rumour was heard. At that point, Vorm was expected to arrive on loan, while KJH was supposed to finally seal a transfer to White Hart Lane. While this particular double deal never materialised in the end, it did give rise to one of the best transfer headlines of that year:

“Vorm is temporary, Klaas is permanent”

Romelu Lukaku

First linked: 2010
Where is he now? Everton

Rewind back six years to the Summer of 2010. Spain had just won the World Cup, Harry Redknapp was a genius, and Spurs apparently had a bid rejected for a Belgian wonderkid called Romelu Lukaku.

Then only 17, Lukaku was attracting admiring glances from all over Europe for his impressive displays for Anderlecht. Despite being little more than a kid, on the pitch Lukaku was already making full grown men look small. At 6’3 and almost 90kg, Lukaku looked more like an NFL Linebacker than a 17 year old striker. Add in the fact he had just hit 15 goals in 33 games in the Belgian league and we suddenly seemed to be looking at a younger clone of Didier Drogba. Anderlecht rejected advances from some of Europe’s elite for two further years, as the player was content to grow in his home country.

In April 2011, it was alleged that Spurs had jumped to the front of the queue to sign the Belgian starlet, only for Chelsea to hijack the move when the window opened, signing the striker for a reported £18million.

Despite hitting 17 goals in 35 Premier League games while on loan at West Brom in 2013, or netting 15 in 31 for Everton the following year, Lukaku failed to convince Chelsea manager José Mourinho that he could lead the line at Stamford Bridge. As a result, Lukaku was allowed to leave the club. Despite fresh links to a move to Tottenham at this point, Lukaku instead returned to Everton, where he had become a fan-favourite the previous season.

At just 23 years old, Lukaku has scored an incredible 119 goals in his 278 professional games. With 60 of those goals coming in his 149 Premier League appearances, he can now legitimately be considered not just a hot prospect, but one of the finest strikers in football. Now believed to have a pricetag of £60million, he appears to be well outside Tottenham’s budget. I’m sure there are many scouts at Tottenham who wonder what could have been.

Eden Hazard

First linked: 2012
Where is he now? Chelsea

“Maybe I’ll go to Tottenham, it’s a great English club. I said I would go to England.”
– Eden Hazard, February 2012

Early 2012 was a great time to be a Spurs fan. Gareth Bale and Luka Modric had grown into bonafide superstars, a new cult hero had arrived in Rafa van der Vaart and Harry Redknapp was orchestrating an unlikely title push. Tottenham’s bright young team looked set to be a Champions League participant the following season, and as a result, became a very attractive destination for Europe’s hot prospects. Yes, in February 2012, things seemed rosey in White Hart Lane, but, as is often the case, Chelsea came along to ruin everything.

Harry Redknapp’s flirtation with the vacant England job caused Tottenham’s momentum to stumble in the second half of the season. Yet as the season drew to a close, Tottenham cemented their place in the top 4, at the expense of a Chelsea team that had floundered in the league under Andre Villas Boas.

Tottenham’s recruitment department were already looking into upgrading the squad ahead of the upcoming Champions League campaign by chasing down a deal for ‘The Belgian Messi’ Eden Hazard. Hazard himself had attracted interest from the likes of Barcelona and Real Madrid, but Hazard wanted first team football assured, and felt a Premier League side, who would play in the Champions League, was the logical next step in his development, before an inevitable move to one of the Spanish heavyweights. His father added more weight to this theory with the following quote:

“Yes, there is interest from Spurs, and no, there’s no offer. The priority for Eden is one thing: games. Opportunities. It might be better to join a club just below the biggest.”

While this could be viewed as an insult to Spurs, very few at Tottenham cared. They were getting one of Europe’s brightest prospects, and even if he did leave for sunnier shores in 3 or 4 years, it would only be for a very hefty price-tag.

And then Chelsea won the Champions League.

It will never fail to amaze me how it happened. Villas Boas got the chop after he lost the dressing room, and the side were trailing 3-1 to Napoli in the Champions League round of 16. Through a bizarre twist of fate, they somehow made their way to the final, where a late Didier Drogba equaliser in normal time, and a missed Arjen Robben penalty in extra-time handed them the most unlikely of victories. The downside?

Only 4 Premier League teams could be allowed contest the following years competition, and with the winners entitled to automatic re-entry, that meant 4th placed Tottenham Hotspur lost out.

Once Champions League aspirations vanished, Hazard’s interest in a move to the Lane evaporated. As if to rub salt in Tottenham’s wounds, who else but Chelsea then waltzed in to pick-up the Belgian winger instead.

Four years on, Hazard is Chelsea’s centrepiece, having been Premier League player of the year in 2014. It’s hard not to wonder what could have been, had Arjen Robben been more accurate from the penalty spot in May of 2012…

Leandro Damiao

First linked: Shortly after the Big Bang
Where is he now? ???

*WARNING: Fight Club Spoilers ahead*

You really didn’t think I’d write a whole article on Tottenham’s most tragic transfer tales and not mention Leandro Damiao did you?

In the Brad Pitt/Ed Norton classic film that is ‘Fight Club’, the main character is in turmoil. His one dimensional life is missing something.

The answer to all his problems arrives when he meets the maverick that is: Tyler Durden.

Super cool, uber-confident, care-free. Durden is the epitome of everything the main protagonist is looking for. The twist? Tyler Durden doesn’t exist. He’s merely a fantasized figment of his imagination, based on everything he wants to be.

My theory? Leandro Damiao is Tottenham Hotspur’s Tyler Durden. Does he even really exist?

United had Rooney. Chelsea had Drogba. Woolwich had RVP. Even Liverpool went from Fernando Torres to Luis Suarez and yet try as they might, Tottenham Hotspur just could not find that elusive star striker. Every great club had to have one, yet despite countless moves for strikers from Roman Pavluychenko and Darren Bent to Jermain Defoe and Peter Crouch, Tottenham just couldn’t find that one 20-goal a season guy, whose name all fans would want on the back of their jersey. Enter: Leandro Damiao

In 2011, Damiao shot to prominence after hitting 14 goals in 28 games for Internacional in Brazil. 6’2, lean and strong, fast and fit, and with a neat eye for goal – he was perfect! Hype grew further after Damiao earned his first Brazil call-up in March of that year. In June 2011, Tottenham were said to have an £11million bid rejected for the striker, yet during that summer, it was said that his next move was to be to either Tottenham or Inter Milan. As it conspired, no move for Damiao materialised from either European club, and he continued to ply his trade in Brazil.

Even as Tottenham changed managers in 2012, new Head coach Andre Villas Boas was still said to be keen on the Brazilian hitman, and a move was said to be in the pipeline for that entire summer as Tottenham desperately chased a striker. Instead, a move for Emmanuel Adebayor was clinched instead, and the mythical Brazilian stayed at Internacional.

As the experiments with the likes of Adebayor and Roberto Soldado were trialed and failed, Leandro Damiao was constantly linked to a move to White Hart Lane during Andre Villas Boas tenure as manager.

Then, in 2014, a tall mobile number 9 with a shrewd eye for goal finally did appear on the same – His name though was not Leandro Damiao, and instead it was Harry Kane who was leading the line at Tottenham Hotspur.

Since that time, Kane has gone from strength to strength and has just come off his second straight +20 goal season. Damiao meanwhile has faded out of relevance. His last appearance for the Brazilian national side was back in 2013, and now at 27, he finds himself on loan at Flamengo, a distant thought from the White Hart Lane faithful.