10. Signing Andriy Shevchenko
In May 2006, Chelsea broke the British transfer record when they splashed out £30 million on AC Milan forward Andriy Shevchenko, with the player stating upon his arrival at Stamford Bridge that the perseverence of Abramovich in chasing his signature
convinced him to make the mega-money move. At first glance, it appeared to have been a huge transfer. The season before, he had plundered 28 goals in 40 appearances for AC and looked every inch a world class striker. However, as we all now know, things did not work out. He lasted just two seasons at Stamford Bridge before being farmed out on loan to his former club for the 2008/09 season. He returned to Chelsea but then suffered the ignominy of being left out of the 2009/10 Champions League squad and was later sold to Dynamo Kyiv. Perhaps one of the most expensive mistakes under Abramovich's era - but not
the most costly, but we will come to that later on...