6. Frank Lampard – Chelsea to Manchester City (2014)
The Stamford Bridge legend’s contract was up with Chelsea, and it seemed that after 13 years that he was on his way for a new adventure in the Major League Soccer.
Prior to his exit, the 36-year-old told Sky Sports, “Having been at Chelsea for 13 years now, I can’t quite see myself playing in the Premier League anywhere else. Anywhere in England really.”
However, the former England international caused immense controversy when he signed a six-month loan deal with the Blues’ Premier League rivals Manchester City, which later turned into a season-long contract.
5. Ashley Cole – Arsenal to Chelsea (2006)
The left-back was famously nicknamed ‘Cashley’ after nearly crashing his car when hearing that Arsenal were only willing to offer him a measly £55,000 per-week.
This signalled the end of his career with the Gunners, but the move was riddled with controversy given the tapping-up scandal involving Cole, his agent, Jose Mourinho and Chelsea chief executive Peter Kenyon in a London hotel.