The return of Jose Mourinho to Stamford Bridge has evoked memories of the great team he built during his first reign as he added the likes of Ricardo Carvalho, Petr Cech and Didier Drogba to a team already containing John Terry, Frank Lampard and Claude Makelele.
However, these impressive signings have shrouded some of Mourinho's poorer dealings in the transfer market. Here is a list containing five of the the worst.
1. Andriy Shevchenko
Former Ukraine captain and AC Milan legend Shevchenko was brought to the Bridge in 2006 for a hefty sum of around £30million.
However, the striker failed to produce the form that led to him being awarded the Ballon d'Or in 2004, scoring a measly 22 goals in 77 appearances.
Whether the signing was made by Mourinho is questionable - Shevchenko's friendship with chairman Roman Abramovich and Mourinho's initial reluctance to play him suggested that it was Abramovich's signing.
It is believed that his failure contributed to the strained relationship between chairman and manager and the subsequent sacking of Mourinho.
2. Mateja Kezman
Another striker who failed to live up to expectations was the Serbian Kezman.
Having finished the 2002/03 season with more than a goal every game and nearly matching that the following season, Chelsea coaxed the clinical finisher from PSV Eindhoven.
The fee was relatively low but Chelsea fans had expected more than the four league goals his spell with the club yielded.
He did, however, score the winning goal against Liverpool in the League Cup Final of 2005. He was hastily sold to Atletico Madrid the following season.
3. Shaun Wright-Phillips
Pacy winger Wright-Phillips was signed by Mourinho for a staggering £21million, with Mourinho vowing to give the youngster plenty of opportunities in the first team.
Unfortunately the England winger was unable to impose himself and failed to dazzle with his mediocre performances.
After three unsuccessful seasons with the Blues he was eventually palmed off to former club Manchester City for a considerable loss.
He scored the winner against Chelsea whilst at Queens Park Rangers in January, condemning Rafael Benitez's side to a 1-0 loss.
4. Asier Del Horno
After an impressive stint with Athletic Bilbao, Chelsea forked out £8million to secure the signing of Del Horno.
The idea had been for the Spaniard - who somehow amassed 10 caps for his country - to fill the problematic left-back spot; however, Del Horno only caused more problems.
His shambolic performance against Barcelona stands out as one of his worst displays as he was sent-off in the first-leg of a Champions League tie which eventually saw Chelsea knocked out, losing 3-2 on aggregate.
5. Steve Sidwell
A very difficult decision for the fifth and final spot, but in the end I have opted for the 'Ginger Ninja', Steve Sidwell.
Although Sidwell was signed on a free from Reading and later sold for a profit, the Englishman failed to produce any performances of note during his time.
Whenever he did play he was clearly a class below the rest of the squad, although his appearances were so rare you could forget he even played for the club.
However, it is with some justification that some argue that he was not given enough opportunities.
Honorable Mentions: Jiri Jarosik, Tal Ben Haim, Maniche, Hilario, Khalid Boulharouz
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