The most momentous transfer deadline day deals, including Arsenal and West Ham signings
Manchester United love a transfer deadline day deal but Arsenal, Chelsea and even West Ham have turned Jim White’s tie a different shade of yellow before.
It’s that time of year again. Transfer deadline day is almost upon us and numerous clubs are scrambling around despite having three months to finalise their summer business.
For the third straight year, Liverpool need a midfielder they won’t sign. Wolves are after a centre-half. Chelsea are desperately searching for reinforcements to their threadbare squad.
The futures of several big names are up in the air, notably Raheem Sterling and Ivan Toney. There is also the Saudi Pro League hovering around looking to hoover up as much talent as possible.
With so much going on, let’s take a look back at the 10 biggest summer transfer deadline day signings ever, or in other words, the ones that made Jim White lose his mind just a bit in a yellow tie.
10) Sergio Ramos – Sevilla to Real Madrid, 2005
Rather bizarrely, Ramos was the first and only Spanish player bought during Florentino Perez’s first presidential reign at Real Madrid. Not a bad one, was it?
Over the course of 16 seasons at the Bernabeu he did it all, winning every single trophy available, including captaining Madrid to three Champions League titles. There were also 671 appearances, an incredible 101 goals from defence and a hilarious 26 red cards in the famous white shirt. The latter two are unsurprisingly club records.
Of those 101 goals, two came in two of his four Champions League final victories, both against Atletico Madrid. The first is perhaps the most important goal in recent Real history, coming deep into added time and pushing the 2014 final into extra time, eventually ending a 12-year wait for La Decima.
READ NEXT: Ranking all 32 Champions League finals, with ’99 Manchester United outside the top six
9) Carlos Tevez – Corinthians to West Ham, 2006
Without a doubt the most bizarre and most controversial deal on this list, there was complete shock when Tevez and fellow Argentinean World Cup star Javier Mascherano turned up at Upton Park with Alan Pardew.
While Mascherano was a complete bust and left for Liverpool just months later, Tevez became a West Ham icon, albeit very late into the season and at a time when everything about the transfer came into question.
He scored his first goal for the club on March 4 in a thrilling 4-3 loss to Spurs, which came just two days after the club was charged with breaking third-party ownership rules – both players’ contracts were part-owned by Kia Joorabchian.
Somehow the Irons avoided a points deduction and Tevez’s seven goals in the run-in kept them up ahead of Sheffield United and Neil Warnock, who were justifiably apoplectic with rage.
8) Ashley Cole – Arsenal to Chelsea, 2006
On the very same day, one of the more protracted transfer sagas also came to a close – and that was not without controversy either.
Cole had been an integral member of Arsenal’s Invincibles but the very next season, he was caught meeting Chelsea pair Jose Mourinho and Peter Kenyon in a London restaurant, with the Blues subsequently charged with tapping up the England left back.
An awkward ‘détente’ then occurred with Cole continuing at Highbury despite being largely disliked by their fanbase and secretly still longing for a switch to West London.
It came about at the death in August 2006 with William Gallas going the other way, where of course he decided to take the 10 shirt left vacant by Dennis Bergkamp’s retirement.
At Stamford Bridge, Cole won everything including the Champions League and four more FA Cups – his personal total of seven is an individual record.
7) Dimitar Berbatov – Tottenham to Manchester United, 2008
The first of two Daniel Levy sagas to feature on this list; it remains a surprise that Harry Kane’s move to Bayern Munich wasn’t quite kicked on until the very last minute.
United were fresh off winning the Premier League and Champions League double and Fergie was looking to add another piece to his already all-star attack of Ronaldo, Rooney and Tevez.
That man was Berbatov, who had showcased Cantona-like traits and ability in his two seasons with Spurs, which no doubt caught the United manager’s eye.
A fee was finally agreed on deadline day but by the other Manchester club (more on that shortly), yet Berbatov only wanted United and Fergie allegedly met him at the airport to ensure there was no way he ended up in blue. Two league titles and a Golden Boot later, it’s safe to say it was a good decision.
MORE TRANSFER FEATURES FROM F365
👉 Twenty biggest transfers in the world in 2024 summer transfer window
👉 The 20 best footballers available on a free transfer right now
6) Robinho – Real Madrid to Manchester City, 2008
The other side of a truly fascinating 2008 transfer deadline day and the day everything changed for both Manchester City and English football as a whole (again after the arrival of Roman Abramovich five years earlier).
City had been purchased by a mysterious Abu Dhabi group and instantly became the richest club in the world. Of course the details of that tainted ownership are better known now but back then, information was limited.
Spending power, on the other hand, was not. Robinho seemed set for Chelsea but City had other ideas, breaking the British transfer record to land the Brazilian for just over £32m. It’s unclear whether the player knew which Manchester club he was joining but it happened anyway.
Robinho’s 18 months in Manchester were up and down but his signing marked the beginning of the modern City, a move away from mid-table mediocrity, and its impact is unquestionable.
5) Mesut Ozil – Real Madrid to Arsenal, 2013
Another two-pronged deadline day deal, which saw the brilliant German playmaker switch from Madrid to London out of nowhere.
Arsenal had endured a shambolic transfer window, infamously bidding £40m +£1 for Luis Suarez before arriving at deadline day having spent no money.
That all changed with a then-record deal for Ozil, who was discarded by Florentino Perez much to the annoyance of Cristiano Ronaldo.
Ozil’s Arsenal legacy is a weird one – capable of absolute magic but so often going missing in big games. He frustrated as much as he fascinated.
While at the Emirates, his greatest moments came with his country, notably the 2014 World Cup win. Three FA Cups was good but it could have been better, and Mikel Arteta was quick to move him on upon his appointment.
4) Gareth Bale – Tottenham to Real Madrid, 2013
Ozil left because Madrid had lined up their latest Galactico, and it was another summer-long story with Levy and Spurs.
Bale had lit up the Premier League in the two and a half previous seasons after being shifted forward from left-back and soon became the target of Real, as well as a post-Fergie United.
Perez viewed him as the long-term replacement for Ronaldo, which annoyed the Portuguese legend even more, but it never materialised largely due to the amazing longevity of Real’s all-time leading scorer.
Still, Bale’s impact and success was unbelievable in spite of injuries and issues with Zinedine Zidane. Five Champions Leagues, winners in the 2014 Copa Del Rey and Champions League finals and over 100 goals for the club says it all. Even if Wales and golf came ahead in his list of priorities.
The best ever British football export.
3) Ronaldo – Inter Milan to Real Madrid, 2002
The original Ronaldo. R9. Il Fenomeno. The biggest star in the football world during the late 1990s and early 2000s.
After a miserable and injury-riddled four years between the 1998 and 2002 World Cups, he made his stunning comeback in South Korea and Japan, scoring eight goals to help Brazil to their fifth crown, and, in the process, announcing his re-arrival as a megastar.
Inter said they’d never sell him but he eventually became the latest and possibly greatest Galactico at the Bernabeu.
His time in Madrid came when Real were a basket case, not even making it past the Champions League round of 16 in any of Ronaldo’s four full seasons at the club. The Brazilian is undoubtedly the best player to never win the trophy – Real won it months before he joined and Milan won it after he arrived in 2007 but he was cruelly cup-tied.
Still, 104 goals in 177 appearances for Los Blancos wasn’t half bad.
2) Wayne Rooney – Everton to Manchester United, 2004
If we were talking strictly best deadline deals, Rooney would be in the top spot.
At just 18 years old, he was already England’s best player, the best player at Euro 2004 and well worth his close to £30m fee, which was a world record for a teenager back then. A testament to just how good he was.
Rooney’s debut had to wait as he recovered from a broken metatarsal but it was worth it. A hat-trick against Fenerbahce let everyone at Old Trafford know a new star was in town.
He never looked back, winning every major trophy with the club, including five league titles and a Champions League. His departure in 2017 brought down the curtain on a glorious era of one of United’s greatest ever, who remains their all-time top scorer with 253 goals.
1) Cristiano Ronaldo – Juventus to Manchester United, 2021
It might have ended terribly and with Piers Morgan, but no-one can deny Cristiano Ronaldo’s return to Manchester United was arguably the biggest transfer ever, let alone just for deadline day.
Social media went into overdrive; every media outlet in the world covered it around the clock. The buzz was insane, simply put.
It could have all been so different with it seeming at one point as though CR7 would do the unthinkable and join City. Phone calls from Rio Ferdinand, Patrice Evra and even Fergie stopped that and led to the prodigal son returning.
His debut and two goals against Newcastle was like something from a movie and perhaps the biggest moment in post-Fergie United history at Old Trafford – which says a lot about the lack of success.
More moments came, both good and bad, in a dire season for the club, as did 24 goals. After just a year back, Ronaldo wanted out and he was duly let go after his embarrassing TalkTV appearance.
It’s unlikely anything will top the sheer hype of that transfer this year or any year.
MORE ON CRISTIANO RONALDO’S RETURN FROM F365
👉 Man Utd had ‘no intention’ of signing Ronaldo before City interest
👉 Ronaldo petrifies players and those Newcastle Nazis
