Stand-in boss Di Matteo faces his date with destiny
Legend or loser? If Chelsea manager Roberto Di Matteo isn't 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 (pictured) chases the London club's first ever Champions League crown at the Allianz Arena tonight, 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 Nicolas 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 not remembered with any warmth by Blues fans.
It is true that Di Matteo has already claimed some silverware with Chelsea securing the FA Cup final earlier this month 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, said this week the pain of his abrupt exit from Chelsea still lingered.
He signed a four-year contract in September 2007 but 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 doesn't get the desired result in Bavaria. Not only will Chelsea suffer more European heartbreak, they will be missing from the competition next season.
The fact of the matter is that Chelsea would probably be better off without their interim boss in charge for next season. But grabbing two trophies in 10 weeks, including the biggest in club football, is one hell of a job application.
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 can't be argued that Di Matteo has done a splendid job since taking over in March from former boss Andre Villas-Boas, who simply didn't have the maturity or street credibility to so rapidly make the dramatic changes he was attempting.
But, as a fine former midfielder in west London, Di Matteo has acted more like a teammate of senior players such as 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.
Don't forget that Chelsea lost 10 games as they finished sixth in the Premier League, 25 points behind Manchester City and Manchester United.
When Carlo Ancelotti was sacked at the end of the previous campaign, Chelsea were second 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 means he is for ever in their hearts.
But on a Chelsea managerial level, Di Matteo's legacy will be defined by tonight's final.
Six days earlier, another Italian, Roberto Mancini, flirted between the two 'L' words as Manchester City left it oh-so late against Queens Park Rangers in the final game of the season.
Securing their first top flight English title in 44 years means he will always be a Manchester City legend.
But if Sergio Aguero's 94th minute goal hadn't have gone in, Mancini might now be without a job and branded a loser.
It could still go either way for Di Matteo.