Milan still seek spirit of Ancelotti as Inzaghi attempts to turn club round

He succeeded where others had failed. On Saturday 24 May in Lisbon, Carlo Ancelotti steered Real Madrid to la Decima, and the tenth European Cup victory which had eluded the storied Spanish giants for a painful decade or more. Other famous coaches – including Fabio Capello and Jose Mourinho – had been sacked for being unable to deliver the trophy so demanded by los Merengues, their reputations somewhat dented by not achieving the one goal demanded by the club’s supporters.

It was not the first time that the Italian coach had ended such a drought – his 2003 triumph with Milan ended a nine-year wait for the Rossoneri, and he would repeat the feat four years later with victory over Liverpool in Athens. The San Siro giants had tried eight different men on the bench as they chased the most prestigious of silverware.

Today, the Serie A club still seem uncertain of where to turn for guidance.

Milan's steady decline since Ancelotti departed in summer 2009 has been shocking to witness; from title winners three years ago to missing out on Europe completely. Massimiliano Allegri inherited a squad laden with talented veterans, but the club failed to replace these ageing stars and gradually the lack of quality took its toll. Their dire financial position meant the sales of Zlatan Ibrahimovic and Thiago Silva were necessary evils, but it is perhaps the manner in which other iconic players were treated which has been most telling.

Over the years, the Rossoneri earned a reputation for taking care of former players, with a string of retired legends handed off-field roles after retirement. Recently, however, their elder statesmen have been unceremoniously dumped, with the likes of Paolo Maldini, Massimo Ambrosini and Gennaro Gattuso all making clear their disgust about how their exits were handled.

Perhaps the greatest of these slights was given to Andrea Pirlo, the midfield genius marginalised by Allegri only to become a central piece in the all-conquering Juventus side whose rise to prominence has counterpointed the Milanese downfall. He was handed nothing but a Cartier pen for his decade-long contribution to the Rossoneri, and relished every opportunity to make Milan pay for no longer believing in him.

Clarence clears his desk

Just two days after Ancelotti was delivering the Champions League to Madrid’s Plaza de Cibeles, another of his former charges was being told his services were no longer required.

Clarence Seedorf only returned to the San Siro in January, calling time on his own playing career to replace Allegri after Milan's disastrous start to 2013/14. But he too failed to lift the ailing club from its shocking slump. Despite a string of five consecutive wins in March and April, the Dutchman managed to collect just 35 of a possible 57 points, and oversaw a comprehensive Champions League exit at the hands of Atletico Madrid.

He never appeared to ingratiate himself with supporters or the club’s hierarchy, and in June followed Allegri by being sacked. There is the inescapable feeling that other, unrevealed factors influenced the decision.

His ill-fated tenure was not helped by a flawed squad and lack of money available to fill those obvious gaps, meaning the situation is unlikely to improve anytime soon. With Barbara Berlusconi and Adriano Galliani struggling to co-exist as joint CEOs, Milan continue to fall further and further behind those above them in Serie A as problems on and off the field grow.

Pipped to the post

Yet, in need of the strong, experienced hand Ancelotti once used to guide the Rossoneri, another first-time coach has been appointed. The new man is none other than Filippo Inzaghi, a figure beloved by all who hold the famous red and black shirt in high esteem, and a former player whose goalscoring exploits were central to the trophies delivered by Ancelotti.

Like Seedorf he has first-hand experience of the environment in which he will be expected to work, having spent 11 years of his playing career at the San Siro. He knows all too well the strained relationship between the younger Berlusconi and Galliani. Unlike his former team-mate, however, he has already coached at Milan, having taken over the club’s U17 side immediately after retiring and earning promotion to the U19s a year later.

That insight into the political machinations above should help him make a smoother transition to the first-team bench, and prevent him from making the same mistakes that ultimately cost Seedorf his job. He will still have the same problems to overcome, and it is difficult to imagine the former striker being able to solve the defensive woes which blighted the tenures of the two previous coaches. Fan expectations will remain high, and the 40-year-old will undoubtedly feel their wrath should he oversee a start as poor as Allegri’s. Milan cannot be out of Champions League contention by Christmas again.

Inzaghi will also be expected to bring many of his own youth team players to the fore, perhaps finally enabling Milan to deliver on their promise of promoting home-grown stars. The club certainly have the talent, with players like Bryan Cristante, Mattia De Sciglio and Riccardo Saponara all pushing for more minutes next year.

His former boss Ancelotti is not worried about this being Inzaghi's first job, rehashing the old adage that everyone starts somewhere. “No one has experience at the start of their career,” Ancelotti told ANSA. “You get it with time; the most important thing is to know the game.”

The club will hope his coaching career can grow as they rebuild, bringing the teachings of his hugely successful playing career to the San Siro sidelines. Welcome to the Filippo Inzaghi era of Milan.