Di Matteo's legacy at Chelsea - and whether he will stay at the helm of the club - is likely to be defined by the outcome of Saturday's Champions League final, argues Jason Dasey
By Jason Dasey
Legend or loser? If Chelsea manager Roberto Di Matteo is not sure about the fine line between the two 'L' words of sport, former manager Avram Grant will be only too happy to remind him.
Di Matteo chases the London club's first ever Champions League crown at the Allianz Arena on Saturday, knowing that victory in the final against Bayern Munich will see him succeed where Grant failed four years ago.
Grant was only a John Terry spot-kick away from glory in 2008 against Manchester United before the Chelsea skipper slipped over in the Moscow mud. When teammate Nicholas Anelka's decisive penalty was saved by Edwin Van Der Sar, United won the shoot-out 6-5 to lift Europe's top club trophy for a third time.
In the same season, Grant's Chelsea were in the English Premier League title hunt until the final day and lost fewer games than champions United. Yet Grant is remembered by Blues' fans with about as much warmth as the city's notorious 1990's Poll Tax.
It is true that Roberto Di Matteo has already claimed some silverware, with Chelsea securing the 2012 FA Cup, while Grant had the ignominy of losing the 2008 Carling Cup final to Tottenham. But winning the fast-devaluing FA Cup will be truly overshadowed by whatever transpires against Bundesliga runners-up Bayern.
Grant, who coached Partizan Belgrade to the Serbian SuperLiga title this season, admitted this week that the pain of his abrupt exit from Chelsea still lingers.
He signed a four year contract in September 2007 yet was sacked in May 2008 by owner Roman Abramovich, just 72 hours after losing the Champions League final.
Di Matteo faces a similar scenario if he does not get the desired result in Bavaria. Not only will the Stamford Bridge club suffer more European heartbreak, they will be missing from the elite competition in the 2012-2013 season.
The fact of the matter is that Chelsea would probably be better off without their interim boss in permanent charge for next season. But grabbing two trophies in 10 weeks, including the biggest in club football, is one hell of a job application.
Is Di Matteo more a mate than a mentor at the Blues?
Benefiting from a classic case of new manager syndrome, Chelsea have also ridden their luck in two memorable Cup runs.
Down the stretch in the FA Cup, they were blessed by favourable refereeing decisions against Spurs and Liverpool that might have altered the ultimate result. And heaven knows how they got through their Champions League semi-final after being battered by Barcelona over two legs.
It cannot be argued that Di Matteo has not done a splendid job since taking over in March from former boss Andre Villas-Boas, who simply did not have the maturity or street credibility to so rapidly make the dramatic changes he was attempting.
But, as a former midfielder and a very good one in west London, Di Matteo has acted more like a teammate of senior players like John Terry, Frank Lampard, Didier Drogba and Ashley Cole instead of a coach.
"Everyone knows who’s running that dressing room," said an unnamed former Chelsea player and ex-England international. "It's not Roberto Di Matteo… it's the players themselves.
"You could see it in Di Matteo’s reaction at Wembley Stadium after Chelsea won the FA Cup. He acted like someone who was looking for his mates to congratulate and celebrate instead of a manager commanding respect."
Even so, Di Matteo has been able to get an ageing squad to perform better than it did under the unpopular Villas-Boas. But this is more like the lingering euphoria of an unexpected Indian summer for Chelsea's veterans rather than anything lasting that will carry the club forward into a new prosperous era.
Do not forget that Chelsea lost 10 games as they finished sixth on the Premier League table, 25 points behind Manchester City and Manchester United. When Carlo Ancelotti was sacked at the end of the previous campaign, Chelsea were the second-placed team in the standings.
Even if Di Matteo falls short in the Champions League final and finds himself without a job, his managerial prospects have been dramatically changed by the last two-and-a-half months.
While he coyly compared the prospect of returning to West Bromwich Albion to going back to an old girlfriend, Di Matteo is now actually out of the orbit of lower and middle-range clubs like the Baggies. His former side Lazio are among the likely suitors in continental Europe.
And, unlike the unpopular Grant, Di Matteo will still be loved by Chelsea fans, even if the Blues find themselves playing in the Europa League next season. Scoring in Wembley Cup finals in the 1990s will forever endear him.
But on a Chelsea managerial level, Di Matteo's legacy will be defined by this third Saturday in May.
Six days earlier, another Italian Roberto Mancini flirted between the two 'L' words as Manchester City left it late at home to Queens Park Rangers in the final game of the season.
Securing their first top-flight English title in 44 years means that he will always be a Man City legend. But if Sergio Aguero's 94th minute goal had not have gone in, Mancini might now be without a job and branded a loser.
It could still go either way for RDM.Join Jason Dasey and guests each week on Goal.com for www.footballfeverpodcast.com: lively soccer discussion with an Asia-Pacific perspective. Twitter: JasonDasey