Worst Ever: Picking an XI of the Biggest Flops to Have Played for Chelsea During the Abramovich Era

When Chelsea owner Roman Abramovich decides to spend, fans don’t know what to expect – especially during summer transfer windows when the club has failed to meet his expectation in the season prior.

Chelsea are currently eight points outside of the Champions League places, and their only real hope of silverware this season is the FA Cup. Needles to say, Chelsea’s owner must be thinking about playing a little Russian roulette. But as we’ve seen in the past, that game can lead to some disastrous signings – enough to field a full-team, as you’ll see below.

1. GK – Marco Ambrosio

It’s 2003 and Carlo Cudicini is in goal when then-manager Claudio Ranieri sets his sights on a substitute goalkeeper. Marco Ambrosio is the name pulled out the hat. 

Ambrosio was limited to few first team appearances after making a number of mistakes against Notts County in the League Cup, but he went on to put in a good performance against Arsenal in the Champions League quarter final where he pulled off some big saves. 

Chelsea went through, but unfortunately the next round didn’t bring as much luck, losing to Monaco 3-1 in the first leg with Ambrosio making a hash of the third goal before being dropped for the second leg. 

He was eventually allowed to leave the club in 2005 because a certain Petr Cech joined and claimed his spot as first team goalkeeper. 

2. RB – Davide Zappacosta

After losing out to Man City for the signature of Real Madrids offensive full back Danilo in 2017, Antonio Conte’s response was to sign unknown Italian wingback Davide Zappacosta for a reported £25m on deadline day.

Was this a sign of intent from Chelsea after winning the league or a message to Mr Abramovich?

Zappacosta gave a good impression by scoring a worldy in a Champions League match against Qarabag, but has since racked up a bunch of mediocre performances this season, not showing any promise or signs of improvement.  

He looks set to be another player heading towards the revolving door at Stamford Bridge.

3. CB – Khalid Boulahrouz

Purchased from Hamburg for £11.7m as defensive cover for the whole back four in 2006, Boulahrouz didn’t have a great year, failing to break into the first team and only playing sixteen games.

In this short amount time he managed to get sent off once, booked twice, conceded twelve fouls and was completely embarrassed by Robbie Keane. The next season he was shipped off to Sevilla where he only played six games, moving on to several different clubs before retiring in 2016. 

4. CB -Tal Ben Haim

Tal Ben Haim started his life at Chelsea with a Charity Shield debut match against Manchester Utd in 2007, and became a regular starter in the short-term thanks to the injuries to Terry and Carvalho picked up.

Once they returned back from injury he fell to fourth choice, dropping behind Alex. He made 16 appearances for the Blues in total but not before the Telegraph reported his fall out with Avram Grant, which ended up costing him a £80,000 fine. He was sold to Manchester City the following year.   

5. LB – Asier del Horno

Asier del Horno was signed in 2005 for £8m and took part in 24 matches, scoring one goal in their Premier League-winning season which was his one and only league winners’ medal in his career.  

It’s unlikely he will be remembered by Chelsea fans for the league title win though, as he was sent off in the Champions League in 2006 for a tackle against Mess.

Chelsea eventually lost the fixture to Barcelona 1-2 with the overall score 2-3 on aggregate.  

6. RM – Shaun Wright-Phillips

Son of Ian Wright and currently plying his trade with Phoenix Rising FC,  Shaun Wright Phillips started his career at Man City making 153 appearances before parting terms and moving to Chelsea in 2005.  

He showed a bit of promise but didn’t fill his potential, only scoring 4 goals in 82 matches, eventually being sold back to Man City in 2008.   

7. CM – Alexey Smertin

Alexey Smertin joined Chelsea for £3.45m in 2003, but was loaned to Portsmouth for the 2003/04 season. He would go on to win a Premier League medal with Chelsea (he made 16 appearances for the team, which was enough to qualify for one).

He scored one goal in the Champions League but didn’t really fit the bill for Mourinho’s new-look Chelsea side. Smertin ended up playing for Charlton and Dynamo Moscow, finishing his career at Fulham.   

8. CM – Ji?í Jarošík

Jarošík was bought for £4.5 million in 2005 from CSKA Moscow and the value probably flattered him, making 14 appearances for Chelsea before having stints at Birmingham, Celtic, Krylia Sovetov, Zaragoza and Sparta Prague and finally ending his career in Spain at Alaves.  

9. LM – Yuri Zhirkov

It all started sort off well for Zhirkov scoring on his debut in a friendly against AC Milan in 2009,  with the Blues eventually winning 2-1.  

The £18m signing made his Champions League debut the same season against Porto, providing an assist on the winning goal.

Although Zhirkov has had his good moments most Chelsea fans were fed up of his lacklustre performances and it didn’t help him having a succession of injuries that stopped him from playing. He left the club in 2011, finishing with just one goal and 11 assists in 49 matches.   

10. ST – Mateja Kezman

Kezman was highly anticipated to be a winner at Stamford Bridge after scoring 105 goals in 122 League appearances for PSV.  

Unfortunately for the Chelsea faithful, he never hit the highs of the prior seasons, managing only 4 goals in 25 attempts. He was sold to Atletico Madrid in 2005 after just one season at Chelsea.

11. ST – Andriy Shevchenko

The most painful pick out of the XI, a legend in the Ukraine and certainly for AC Milan with a goal scoring record to make your mouth water. Roman Abramovich used his pulling power and is understood to have bought Shevchenko for a record fee of £30.8m.  

He failed to make an impact, scoring only 9 goals in his 3 years at the club after being hampered with injuries, even a loan deal with Milan didn’t end his goal drought, where he failed to score in 18 starts.  

Shevchenko was undoubtedly one of the greats of his era but it was maybe too late in his career at Chelsea. He eventually moved back to his first club Kiev and even tried his hand at politics.   

12. Manager – André Villas-Boas

Probably the best and worst thing to happen to Chelsea, coming from Porto for a record fee of £13.3m in 2011, making him the youngest manager in the Premier League at the time.

He had a good pre-season, winning every match, although he didn’t follow through to the season losing big games and dropping out the top four.

Villas Boas eventually got the sack bringing Roberto Di Matteo in, who in turn helped Chelsea win the Champions League in 2012.   


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