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Ever since they sacked Mourinho following a disappointing start to the 07-08 season, Chelsea have always looked like a team in transition, reeling without a stable identity on the field as well as off it. With incredible amounts of money to throw around, they imitated Real Madrid albeit without the solid fan base and the immense heritage.

This year has presented a rough ride to the Blues fans after Scolari’s mid-season disintegration and the indifferent Hiddink’s face saving swoop. Amidst Abramovich’s dwindling fortunes, Scolari was a last gasp attempt to associate grandeur with Chelsea. The tough-minded Brazilian exuded class after his World Cup winning exploits and immense success with Portugal. None would have expected him to lose the big games and the dressing room rather than birthing an attacking mentality graced with flamboyancy. However, it did happen and suddenly, crisis set in. With Hiddink making clear his intentions of going back to coaching Russia (His frankness and indifference to the Chelsea throne, ironically, made him a fan-favourite), speculation went rife about the new gaffer in summer. Stability was needed and the club knew it. So here we are at the start of another season with renewed hopes and a new world-class manager.

Carlos Ancelotti’s tenure will start amidst intense polarity in opinion regarding his appointment. Is he the right choice for Chelsea? Will he lend the glitzy identity Abramovich so sorely craves? Will they finally win the Champion’s League?  Aah! Questions not even the astute astrologer can answer, yet the questions can’t stop pouring in!

One way to see how a person will perform is to know how he has performed in the past keeping in consideration the conditions he performed in.

The Champion’s League is nothing new to Carletto. As a player he was part of the Milan squad that won consecutive European Cups in 1989 and 1990. During this time, Milan played with one of their finest teams ever assembled in that decade, with Maldini, Franco Baresi, Mauro Tassotti and Alessandro Costacurta in defence, Frank Rijkaard and Donadoni in midfield and Marco van Basten in attack. He’s won it twice as a manger with Milan, after taking them to 3 finals in 6 years, an incredible ratio.

You may recall him nursing the ageing legs of the Milan squad which has failed to even qualify for the Champions League in the last season, of old players like Maldini, Gattuso and Pirlo . They even got knocked out of the UEFA Cup after losing to Werder Bremen sans their inspirational playmaker Diego. But before you condemn his abilities, let me remind you that at the start of his decade he took over a similarly ageing squad in Milan. He created the roles of soon-to-be instrumental players such as Pirlo, Gattuso, Seedorf and Kaka, laying the foundations for many a European conquest. Bringing in Inzaghi from his former club Juventus, he formed a dynamic attacking duo in Shevchenko and Inzaghi who would spearhead the Milan attack for many years to come. He created one of the best teams of the decade, as big as the Galacticos of Madrid, thus recapturing the dream team that he himself was part of as a player.