Remembering Andriy Shevchenko at Chelsea: a star who was set up to fail

José Mourinho had every reason to be smug.

It's May 2006. X-Men: The Last Stand is stinking up the box office and Gnarls Barkley sits top of the charts with Crazy, a song that falls into the ‘it sounded good at the time but is now completely unlistenable' category.

Twitter, just two months old, is not yet the depraved cesspit of memes and nonsense we can't help but frequent nowadays.

Back then, Mourinho's hair was darker, his clothes seemed sharper and he was more likely to give the camera a cheeky wink instead of a curled lip.

He had just led Chelsea to back-to-back Premier League titles, spreadeagling the table by 12 points in his first season, and eight in his second.

And, as he basked at the summit of the English game, Roman Abramovich smashed the British transfer record to give him Andriy Shevchenko from AC Milan.

Already in possession of the best squad in the Premier League and having just signed the Terminator of goalscoring, what could possibly go wrong?

Well, in keeping with Chelsea's wildly fluctuating fortunes when it comes to signing strikers in the Abramovich era, quite a lot. Let's look back on Sheva's time at Stamford Bridge.

European credentials

The Premier League had been conquered. Naturally, the Champions League was next on the list.

Abramovich had already bolstered Mourinho's midfield with the capture of Michael Ballack on a free after the Germany captain left Bayern Munich.

Amusingly, given Chelsea's Euro ambitions, they had signed a player often accused of failing to bring his A-game to the Champions League (during his four years in Munich, Bayern never progressed further than the quarter-final).

But no such accusation could be levelled at Shevchenko. The 29-year-old arrived in England as the most prolific striker in European Cup history.

He finished tied with Manchester United's Dwight Yorke as the top scorer with eight during the 1998/99 season while he was still with Dynamo Kyiv and continued to decimate defences in the Rossoneri's famous red and black strip.

The apogee of his time with Milan was converting the Champions League-clinching penalty at the end of what was probably the most boring final of the modern era, as Carlo Ancelotti's side played out a 0-0 stinker with Marcello Lippi's Juventus at Old Trafford.

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Shevchenko memorably failed from 12 yards to gift Liverpool the European Cup two years later but, when he signed for Chelsea, he was fresh from netting 15 in last 22 Champions League appearances.

Rather understandably, Abramovich thought he'd found the missing piece.

Sheva arrived at an interesting time for Chelsea's forward line. Eiður Guðjohnsen and Carlton Cole, both deemed surplus to Mourinho's requirements, left the club while Salomon Kalou was signed from Feyenoord.

The Drogba Factor

But Didier Drogba, to whom Chelsea turned after Shevchenko rejected their advances in 2004, was unhappy. After plundering 32 goals in his first two years at the Bridge, the Ivorian suggested he would welcome a move away and sparked frenzied speculation over his future when he pulled out of Ivory Coast's World Cup training camp for a couple of days.

Mourinho, however, refused to entertain such a scenario and assured the striker that, despite Shevchenko's presence, he remained an integral part of Chelsea's attack.

And so, with Drogba somewhat reassured, the Premier League champions approached the 2006/07 season with their squad in rude health.

Indeed, for the curtain-raising Community Shield against Liverpool, Mourinho named a team which included John Terry and Ricardo Carvalho in defence, Ballack, Michael Essien and Frank Lampard in the centre, Arjen Robben out wide and the Drogba-Shevchenko axis in attack.

The £30.8million striker started promisingly. His wonderfully assured finish – chesting down Lampard's diagonal pass before side-footing beyond Pepe Reina – brought Chelsea level before the break. He would have had a second, too, had it not been for the Spanish keeper's supreme shot-stopping powers.

Chelsea lost 2-1 but it was all good on the Sheva front. The 2004 Ballon d'Or winner had marked his English football debut with a trademark finish and seemed poised to make a seismic impact in west London.

Instead, during an increasingly vexatious debut campaign, he watched on as Drogba, the centrepiece of Mourinho's attack, garnered acclaim after 33-goal haul, surpassing his combined tally for his two years at Chelsea.

The defeat of Liverpool that September was a fine illustration of the landscape that would fuel Shevchenko's frustrations. Drogba assumed centre stage with a stunning turn-and-wallop winner, cementing his status as the club's chief matchwinner. With Tiger Woods in attendance at the Bridge, the Ivorian upstaged his more expensive partner.

From there, it didn't get much better for the No.7. He failed to score in his first three Champions League appearances for the club and, with words like ‘underwhelming' and ‘transition' being used, Mourinho acted, shifting him out to the right for the trip to Reading (a game remembered for Petr Čech's fractured skull).

It didn't work. Hooked off after 63 minutes, he cut a disconsolate figure as he took his place among the substitutes. Next time out, again starting on the wing, Shevchenko scored his first goal in nine games, helping to down Portsmouth after sweeping home Robben's cross.

That goal did little to quell criticism of the striker, though. Mourinho, who underwhelmed by the new recruit's output, rejigged his system to a 4-3-1-2 for the visit of Watford to Stamford Bridge.

Again, Drogba stole the headlines with a hat-trick while his teammate, despite scoring one and assisting another two, made do with footnote status once more. Drawing defenders to him, Shevchenko's presence opened up space for Drogba but that nuance was often overlooked when the tabloids sharpened their claws and got ready to file.

Mourinho's post-match comments were interesting. “He is on top of his game and I don't see anyone else playing and scoring like him in Europe right now,” the manager beamed.

He couldn't envisage Shevchenko, a Ballon d'Or winning marksman, emulating Drogba's Hornets-decimating form at some point? Ouch.

Shevchenko saw it differently. “I wasn't the key of the attack,” he said in May 2007. “I was playing further behind, away from goal – different from how I played at Milan, and maybe that's why Drogba scored so many goals this year. At Milan, I played in my natural role. Here I had to adapt to be something else, and I did it so I could help the team.”

Of course, the forward's maiden Chelsea voyage was far from being a total bust. Despite post-World Cup fatigue, tactical restraints and niggling injuries, he contributed 14 goals and 12 assists, which included important strikes against Porto and Valencia in the Champions League knockout rounds.

Pawn in Mou-Roman Fallout

The biggest storyline, sadly, revolved around Shevchenko's unwitting place at the centre of escalating tensions between Abramovich and Mourinho.

The manager, frustrated at a lack of January signings, dropped Shevchenko and effectively told the Russian owner: ‘back me or sack me'. Aware of Abramovich's close friendship with the former European footballer of the year, Mourinho expected the axe to fall on his head.

It didn't but, from there, things soon went downhill. Chelsea relinquished their league crown to Manchester United and lost on penalties to Liverpool in the Champions League semi-final, denying Shevchenko the chance to beat his former side Milan in the Athens showpiece.

Mourinho eventually did leave, of course, calling time on his trophy-laden reign in September 2007 after his long-standing differences with Abramovich had become irreconcilable.

Naturally, Shevchenko scored the final goal of his tenure, a header to ensure the Blues didn't fall to an embarrassing defeat at home to Rosenborg.

Remembering Andriy Shevchenko at Chelsea: a star who was set up to fail

Unfortunately for the player, Mourinho's departure was not the prelude to greater fortunes. Abramovich drafted in little-known Avram Grant as a stop-gap successor and, while he was seen as a softer man willing to cede to the owner's demands for Shevchenko to start, the striker continued to perform a bit-part role. He spent much of the 2007/08 campaign either on the bench or injured.

Left on the bench for the entire 120 minutes of Chelsea's Champions League final defeat to United in Moscow, a summer exit seemed probable.

Already dreaming of a return to Italy, Sheva's fate was sealed by Luiz Felipe Scolari after the Brazilian admitted he didn't see the Ukranian fulfilling a major role under him.

Shevchenko joined Milan on a season-long loan and returned to Dynamo Kyiv in 2009 before hanging up his boots in 2012.

Some Chelsea fans feel that had Abramovich kept his beak out of first-team matters, Mourinho may have found a way to incorporate him.

This writer takes a different view, however, Shevchenko, who turned 30 a month after his Blues debut, had already played nearly 600 games for club and country before he arrived in England. He struggled with the style of the Premier League, too, often taking an extra touch and getting caught in possession instead of moving it on quickly.

Throw in a World Cup hangover and a bruised ego at playing a supporting role to Drogba, Shevchenko was never really going to work for Chelsea. He is not fondly remembered around Cobham. At least he's not Mateja Kežman.

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Gavin Davison

Gavin is a full-time copywriter based in the UK and has developed in-depth knowledge of the igaming world by working in the betting industry for over five years. During this time, he has written thousands of articles covering various topics, including bookmaker reviews, ‘how to’ guides, bonus comparisons and much more.