Since becoming an integral part of British football, one can easily recall the amount of transfers to have come in and out of Chelsea that have succeeded in the last decade or so.
However, there are some players that the club have let slip through their grips that, on recollection, Chelsea may have been better off keeping with their ranks.
Whether it was on a free transfer or for great sums of money, the following players should perhaps have been kept at Stamford Bridge.
It may be for the player that they were at the time or for the player that they went on to become, but Chelsea can consider it a regret that they didn’t keep these players in West London.
Whether or not the 23-year-old is deserving of his place at the Etihad Stadium, the fact that Premier League champions Manchester City have chosen to invest in the talents of Scott Sinclair speaks volumes.
The winger came to Chelsea as a fresh-faced 16-year-old but spent most of his time as a Blue outside of the club on numerous loan spells.
It wasn’t until 2010 that Sinclair truly started to show glimpses of the potential that made him such a prospect as a teenager, contributing massively as the star performer in Swansea City’s promotion season.
On his return to the English top flight, there were concerns that Sinclair would still fail to perform amongst England’s elite, but he quickly proved his doubters wrong, starring once again in a shockingly successful campaign for the Swans.
While it may have taken him a few more years to exceed as he was expected to back in the mid-2000s, Chelsea may have retained the services of a potential England international had they been just a little more patient.
Offloaded due to circumstance, Tore André Flo is a rare case in that he actually wanted to leave Stamford Bridge at the time of his departure.
The former Norwegian international was sold to Rangers just as he was coming into his playing prime and really should have been given his desired playing time.
As it was, however, Gianluca Vialli ensured that squad rotation remained a key part of his squad and that fellow Italian Pierluigi Casiraghi received his share of games, although he really shouldn’t have.
Flo was decently prolific in West London, never failing to hit less than 13 goals in any of his three full seasons with Chelsea.
That being said, the 2000 arrivals of Jimmy Floyd Hasselbaink and Eidur Gudjohnsen ensured that Flo was once again rotated throughout his waning days at Stamford Bridge, despite being a proven Premier League talent.
In his time with the Blues, Flo won the FA Cup, League Cup, UEFA Super Cup and UEFA Cup Winners’ Cup, all of which he contributed largely towards.
Going on to have a successful spell at Rangers, Flo’s story could have been one of a more illustrious quality were he given the chances that he so desired.
The first purchase as part of Roman Abramovich’s ownership of the club, one could say that the current blueprint of Chelsea’s current transfer policy all started with Glen Johnson.
Bought from West Ham for a fee of £6 million, Johnson is a great example of a player who didn’t hit his prime until becoming a big fish in a slightly smaller pond.
In this case, the small pond would be Portsmouth, and it was on England’s south coast that Johnson made a great name for himself as a surging right-back capable of making great contributions in attack.
One can certainly say that Chelsea were wrong to let Johnson leave by the fact that reports emerged at the time of his Portsmouth departure claiming that the Blues had indeed lodged a bid to bring their former player back to Stamford Bridge.
Liverpool eventually won the race for Johnson, and the defender’s staggering rise in worth to over £17m shows just how far he’s evolved since his days with the Blues.
A former top scorer for the Chelsea Under-18 side, Miroslav Stoch’s lack of involvement within the club’s first team could perhaps be attributed to the fact that his tenure came in conjunction with the Blues’ biggest spending period.
The Slovakian international was signed by the English giants as a teenager, and while he may have made massive influences within the youth ranks, the likes of Deco, John Obi Mikel, Florent Malouda and others ensured that he would never quite live up to his potential.
Now impressing at Fenerbahçe, Stoch is an established Slovakian international and has been a large part of Fener’s success since moving to Turkey in 2010.
Still only 22 years old, Chelsea may not have had to fork out on the signatures of other wingers had they had more faith in a youngster already at the club.
An eight-year veteran at Stamford Bridge and beloved fan favourite amongst many of its inhabitants, one would be hard-pressed to blame Didier Drogba for wanting to leave the club on the high of an FA Cup and a Champions League victory.
The Ivorian international opted not to sign an extension to his Chelsea contract last summer, although there was speculation that the deal he was being offered simply wasn’t long enough.
Regardless of his 34 years of age, advancements in medicine and technology have prolonged the use of the modern day footballer, and Chelsea would undoubtedly have been smarter to hand Drogba the length of contract desired.
In eight seasons at Stamford Bridge, Drogba managed to net on over 150 occasions, contributing more than 70 assists in the process.
That kind of prolific scoring is difficult to come by, and with Fernando Torres being the squad’s only out-and-out striker at the moment, the current Premier League leaders should have done more to hold onto the superstar forward.
Roman Abramovich seems open to spending big in order to bring foreign assets into his side, but sometimes spending less to retain a proven star is the more economical option.
Having featured in five major international tournaments as part of the Dutch national side, it goes without saying that Arjen Robben is a player of vast quality.
While the financial benefits reaped from his €35 million sale to Real Madrid were vast, the winger’s talent alone could have brought more silverware to the club since his departure, making up for that money.
Originally purchased from PSV for around half that sum (€18 million), Robben’s case is a classic example of how business can sometimes supersede the interests of football success and the search of trophies.
After a successful spell with Real Madrid, Robben now finds himself as one of the key players in a massively talented Bayern Munich squad.
Despite playing on the wings, Robben has proven himself to be a huge asset in scoring goals and regularly contributes in the double figures in a single season.
One of Jose Mourinho’s last transfer deals as manager of Chelsea was organising Robben’s sale to Real Madrid, meaning the Blues regrettably lost more than one superstar talent in the summer of 2007.