However, they have equally had their fingers burnt based on their decisions to cut short the stay of some of the raw talents they signed at younger age, only to go on and shine bright and for the club to later realise they were wrong.
In some instances, it is fair to say that it is the neither club nor player to blame but rather a number of unforeseen circumstances that rendered a short ineffective spell to some of these exceptional players.
Certain decision have certainly cost Chelsea dearly, and it is not only the impact these players would have made on the field that was wasted, but also finances.
Here are five players Chelsea should have thought twice about before selling them off;
5. Michael Ballack
4. Arjen Robben
Arjen Robben #16 of Chelsea FC against Club America on July 14, 2007 at Stanford Stadium in Palo Alto, California. Chelsea won 2-1.
3. Romelu Lukaku
Romelu Lukaku of Chelsea holds off the challenge from Ron Vlaar of Aston Villa during the Barclays Premier League match between Chelsea and Aston Villa at Stamford Bridge on August 21, 2013.
2. Kevin De Bruyne
Kevin De Bruyne of Chelsea in action during the Barclays Premier League match between Chelsea and Hull City at Stamford Bridge on August 18, 2013 in London, England.
1. Mohamed Salah
Mamadou Sakho of Liverpool and Mohamed Salah of Chelsea battle for the ball during the Barclays Premier League match between Liverpool and Chelsea at Anfield on April 27, 2014 in Liverpool, England.
All these players could have either guaranteed Chelsea more silverware or have really gone on to prove their former bosses wrong by prospering beyond the confines of Stamford Bridge.
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