Transfer Deadline Day: The Deals That Shocked The World

Former Chelsea defender Ashley Cole, right.
Former Chelsea defender Ashley Cole, right, in Cardiff, Wales, May 11, 2014. Cole made a controversial transfer from Arsenal in 2006. Ben Stansall/AFP/Getty

Transfer deadline day is a peculiar phenomenon of modern football, hyped by television and, more often than not, producing little plaintive howls from legions of supporters desperate for shiny new signings.

And yet, the confected drama has, on occasion, produced compelling narratives.

Here, Newsweek picks three of the most controversial deadline day deals of all time.

Ashley Cole: Arsenal to Chelsea, 2006

Cole had been a part of Arsenal's Invincibles side that went through 2003-04 unbeaten under Arsene Wenger. He was commonly regarded as England's, if not the world's, best left back. Things turned sour, though, when Cole rejected a new contract offer from Arsenal, memorably describing in his autobiography how he nearly "swerved off the road" when told that all Arsenal would offer him was £55,000 a week in wages.

The upshot? Cole made another PR move that damaged him in the eyes of Arsenal supporters, with a transfer to fierce rival Chelsea. He did, however, pick up a Champions League winners' medal, and remained one of world football's best defenders for the next decade as Arsenal went through a protracted drought in the Premier League.

Robinho: Real Madrid to Manchester City, 2008

The Brazilian forward signed for City on a day when the club redrew the landscape of English football. A £32 million deal was sealed on the same day in 2008—September 1—that City came under new ownership, with the billionaires of Abu Dhabi United Group taking control.

As if to stress the point that English football's new superpower had arrived to usurp the old, Robinho was plucked from under the nose of Roman Abramovich at Chelsea, and mistakenly thanked Chelsea for signing him as he completed his move to City.

Despite flashes of brilliance in his first season, the deal hardly worked out, as Robinho returned to his youth club, Santos, in 2010 on loan.

Carlos Tevez: Media Sports Investment Limited to West Ham United, 2006

Tevez came in a double package from Corinthians in Brazil with fellow Argentine Javier Mascherano, a deal whose ramifications are still felt a decade later. Tevez made a crucial goalscoring contribution as West Ham avoided relegation from the English Premier League. But the club was fined £5.5 million ($7.2 million) for breaching the league's transfer regulations.

Worse still, Sheffield United, which was relegated instead of West Ham on the final day of the season, took legal action against the club and ended up with a settlement of £20 million.

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Newsweek is committed to challenging conventional wisdom and finding connections in the search for common ground.

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