“Gatsby believed in the green light, the orgastic future that year by year recedes before us. It eluded us then, but that’s no matter—tomorrow we will run faster, stretch out our arms farther. And then one fine morning— So we beat on, boats against the current, borne back ceaselessly into the past.” – Nick Carraway (The Great Gatsby, 1925)

A filthy rich recluse whose personal life is shrouded in secrecy, and whose enormous wealth has been amassed in morally – if not legally – dubious means? A thing for yachts and lavish parties that feature famous people? Roman Abramovich's similarities with Gatsby, however, do not end there. Most saliently, they also have in common their pursuit of a quixotic dream. Gatsby’s is symbolised by a green light on a dock, and is essentially his obsession for Daisy Buchanan, his former lover – a longing for the past.

Abramovich’s dream is a little more nebulous. It seems to be some sort of intoxicating mix of attractive football and long-term stability. The first half of the 2014-2015 season under Jose Mourinho was the physical manifestation of at least part of that dream. What has happened in the months since, however, has left Chelsea Football Club facing an existential crisis.

The deluge of anger and frustration that descended upon Stamford Bridge in the aftermath of Mourinho’s departure was not aimed merely at the players, but also at Abramovich and the board. Although the Portuguese’s dismissal was perhaps an inevitable consequence of how football works in the modern day, the overwhelming majority of Chelsea fans acknowledged that the problems at the club were the consequence of collective failure at almost every level of the institution.

When Mourinho first left the club, there were rumours that part of the friction between him and the Chelsea hierarchy had to do with the style of football his team played, which did not sate Abramovich’s desire for ‘entertaining’ football. Caretaker manager Avram Grant more or less confirmed that in his first press conference as Blues manager when he said, “Football is also entertainment. We need to win games and fight for the trophies but I think the way we do this and win is also important. To play good and positive football…”

Apart from what now seems like a slightly anomalous 2009-2010 campaign, Chelsea’s success under Abramovich has largely come from being a defensively resolute, physical, counter-attacking unit. The attempt to move away from that style was accelerated after the departures of the old ‘spine’ – Ballack, Essien, Lampard, Drogba among others – and the signings the club has made in the past few years are evidence of the fact that Chelsea have tried to establish an identity for the team radically different from what it was in the early years of the Abramovich era.

Not only has the club failed in doing so, but almost as a direct consequence of it, the Chelsea first-team squad now mirrors some sort of a Frankenstein monster – a leg here, an arm there, utterly lacking in direction and identity. The continued cycle of managerial sackings has obviously not helped in that respect, but the problems up the chain have never really been addressed by Abramovich. In fact, one wonders if the Russian even believes there is a problem.

Michael Emenalo was brought to the club by Grant in 2007, and after serving as opposition scouting head and assistant first-team coach in the past, the Nigerian now holds the important position of the club’s technical director. Much of the ire of Chelsea fans this season has been directed at Emenalo – a sentiment precipitated by the signings of Michael Hector and Papy Djilobodji after the failure to land Everton’s highly promising young centre-half John Stones.

While there is no doubt that Emenalo has also been useful to the club and been involved in more successful signings, there is a sense that Mourinho has, to some extent, paid the price for the Nigerian’s failures as well. There is something seriously wrong at Chelsea if the technical director is not held at least partially responsible for the imbalance in the current first-team squad, with the ‘style’ of several of its members incongruous with the expansive football Abramovich wants to see at the club, or indeed for the conspicuous lack of future planning when it comes to replacing a rapidly ageing defence – Cezar Azpilicueta the only member of it in his ‘peak’ years.

The club’s football board comprises David Barnard, who has an administrative role, Eugene Tenebaum and Marina Granovskaia, both of whom have backgrounds in corporate finance and have been employed in the past by Abramovich’s oil company Sibneft (sold in 2006), and also Bruce Buck, a high-profile lawyer. In other words, Emenalo is the only member of the hierarchy with a genuine football background. Perhaps one of Abramovich’s flaws is that he has always seemed to place too much trust in those close to him, and given the sycophantic yes-men that surround billionaires such as him, one wonders if the advice he gets is not just a rehashed version of his own opinions and thoughts about the football operations at the club.

With issues as deep-rooted as this, the notion that Chelsea can lure Pep Guardiola in the summer with a blank cheque is ludicruous. The Spaniard would take one look at the first-choice back five (Courtois included) and their patent inability to play out from the back, and sprint in the opposite direction. It is a sad indictment of the mismanagement higher up at Chelsea that the club that could once lure the best managers and players in the world now seem miles away from being able to do so.

Manchester City have received a lot of criticism for their seemingly indiscriminate spending in the recent past, and although they have not been perfect, what they have clearly been successful at – more than any other club in England in the past few years – is the implementation of a clear identity, not only in terms of the style of football, but a holistic view towards the club’s development from top to bottom.

City appointed executives Txiki Begiristain and Ferran Soriano, both with experience at the absolute cream of the European crop at Barcelona, and did not hesitate to move away from Roberto Mancini and towards a certain way of playing under Manuel Pellegrini. It almost seems like every action they have taken in recent years, including expanding their stadium and developing their youth academy to a level where it is now among the best in the country, has led to the summer of 2016 and the expected appointment of Pep Guardiola.

Guardiola’s current employers Bayern Munich are one of the gold standards in terms of running a football club, and the Bavarian giants’ board of directors features the likes of Karl-Heinz Rummenigge, a former Bayern player with a glittering career who is now the executive board chairman, and sporting director Matthias Sammer, who not only had a stellar playing career, but was also employed in much the same position for six years by the German Football Association (DFB) prior to being appointed in his current role.

That is the sort of institutional set-up it takes to lure a manager who needs to be able to operate as autonomously as Pep Guardiola. Abramovich does not have anything close to it at Chelsea, but more crucially, it seems as though he himself lacks the conviction to realise his dream – to reach his green light. It would be a minor miracle if the Blues’ board ever chooses to appoint an as yet unproven manager with a great vision over one of the best and most established managers in world football. That is precisely what Barcelona did in 2008 when they appointed Guardiola over Mourinho. That is conviction.

For Chelsea, the first step towards reaching the level of Europe’s elite has to be self-reflection – an understanding of where the club is currently, where it wants to go in the future, and the image it wants to portray to the world. A director of football (or a technical director, if there is an appreciable difference between the two) with more technical expertise than Emenalo and a significantly bigger reputation in world football could be the first step towards achieving that.

Long-term managers increasingly seem anachronistic in the modern football environment, and as such, a strong leader (possibly a director of football) on the club’s board could play a huge role in ensuring that the club does not deviate away from its philosophy even though managers may continue to come and go. Despite manifestly lacking in football expertise, the Chelsea board have time and again taken decisions regarding managers in the interest of ‘protecting the club’, without ever seeming to know what it is they truly want.

Abramovich has to ensure that his vision – if he truly has one for the club and believes in it – is reflected in the choices the club makes, in terms of appointing a manager as well as signing players. If he is not willing to upgrade on Emenalo or potentially appoint someone above him to help provide the club with some much-needed direction, he has to back his next manager all the way and give him the time to build a team in his image – even if that means accepting failure in the short term.

Chelsea have a crucial few years ahead of them with the expansion of Stamford Bridge and the rebuilding of a broken squad, and continuing to operate in the manner they have will not get them any closer to Europe’s best. Abramovich must change his ways, or he risks being stuck in the past – forever gazing wistfully at the green light as it recedes further and further away from him.