The Italian took on the role of Bambi's mother in his short time at the club. He gave birth to a hopeful gush of youth before receiving a fatal bullet that confirmed he would never witness his creation in full flow.
Di Matteo survived one bite of the poisoned apple before his eventual demise. He took a gulp, chewed it up and spat it out as Didier Drogba scored the vital penalty that confirmed Champions League success. His great triumph propelled him toward a new contract—a reward that turned out to be as paper thin as it first seemed.
He was never a long-term solution to Chelsea's plans. In managerial terms, the 42-year-old is relatively inexperienced when you consider him alongside the bosses of Europe's elite. He spent 12 months plying his trade at Milton Keynes Dons and two years at West Brom—this was never going to be enough for a prolonged stint at the top.
Unfortunately for the likeable Italian, football's wicked stepfather struck again. Roman Abramovich continued his ruthless streak by casting a spell of execution upon Di Matteo's head. The Russian overlord—so irked at his team's 3-0 defeat to Juventus—proved he isn't the fairest of them all once again.
This storyline is becoming too predictable. Abramovich is the only man who has the power to turn the pages at Chelsea. His fairytale ending took place six months ago in Munich. The next chapter was meant to be one of galvanisation, continuity and success.
Instead, the Stamford Bridge storyline has descended into nightmare. Chelsea's high-flying start to the season continues to ebb away, leaving the club trailing in the Premier League and on the brink of a European exit.
Abramovich needed to stick or twist. Di Matteo should have been allowed to fulfill his two-year contract at the very least. If that was never going to happen, he shouldn't have been hired on a full-time basis. Abramovich placed the former Chelsea player into the role of Prince John; although a crown lay upon his head, it barely fit.
London's richest club continues to attract unsavoury headlines. Referee Mark Clattenburg was accused of racially abusing John Obi Mikel a few weeks back. Chelsea failed to produce formal evidence to reinforce these claims, leading the Metropolitan Police to drop its investigation (via The Daily Mail).
John Terry's racial abuse of Anton Ferdinand also received punishment earlier this season. Although the former England captain is now sidelined with injury, his conviction intensified villainous hate toward the battle-worn defender.
Such incidents are quickly painting Chelsea's recent history as the darkest fairytale in football. The elation of capturing Champions League glory quickly subsides when the club is halted through questionable decisions.
Abramovich may have installed himself as Chelsea's Big Bad Wolf, but it's the players who must huff and puff to overcome the challenges ahead. The new era begins with an important Premier League clash against Manchester City—a test that could signal a change in fortune for the struggling squad.
Amongst the thorny undergrowth of the club's backroom, Chelsea have plenty of individuals that can dig them out of this mess. The twinkle toes of Juan Mata, Eden Hazard and Oscar could provide some much-needed sparkle. Experienced individuals such as Ashley Cole and Petr Cech must ensure an air of authority remains across the uncharacteristically flimsy team.
Dare I say it, Fernando Torres might just hold the key that brings this all together.
Chelsea have confirmed Rafa Benitez as the club's new manager (via The Daily Mail). Can the Spaniard bring the best out of Torres? Once again, this is down to the player himself. He failed to impress under Carlo Ancelotti, Andre Villas-Boas and Roberto Di Matteo—how much confidence can the new manager instill?
If the new boss turns Chelsea's £50 million beast into a goal-scoring beauty, it wouldn't have happened through a lack of chances. Abramovich is almost forced to keep faith in his misfiring forward—the price tag needs some sort of justification.
Torres is being handed another chance to stake his claim at Stamford Bridge. Di Matteo, despite his success, was never afforded that opportunity. Abramovich was more than willing to say goodbye to his frog without the need to pucker his lips.
I hope Rafa Benitez was installed with the right intentions. Prolonged success will never happen if Abramovich forces his managers to walk the plank at every opportunity. The Russian's reign must start prioritising brains over financial brawn. If it doesn't, Chelsea's squad will only ever amount to a group of lost boys.
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