They possess 36 Scudetti, 12 Coppa Italia, 12 Italian Super Cups, 2 Club World Cups and 10 European Cups between them. Only Madrid can call itself a more successful European footballing city in terms of the magnitude of success, and they boast that shy, retiring football club that goes by the name of Real. This is an area that boasts Paolo Maldini, Franco Baresi, Walter Zenga, Roberto Donadoni, Gianluca Vialli and Giovanni Trapattoni in its alumni of graduated legends of the game. It has a distinctive and iconic 80,000 seater arena to call home that is a staple on any self-respecting football supporters bucket list. Yet, Milan as a city is struggling to make an impact on Italian football let alone on the rest of Europe. Associazione Calcio Milan – we will stick to Milan for now – and F.C. Internazionale Milano – Inter, because it’s easier – currently occupy 6th and 7th in the Serie A rankings respectively. They currently reside behind the cities of Turin, Rome, Naples and Bergamo; no place for this one of Europe’s footballing princedoms. It begs the question, what exactly has gone wrong in Milan?

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A Supercoppa Italia in 2016 aside, it has been 6 years since Milan lifted a meaningful piece of silverware. Inter lifted a Coppa Italia in 2011 after Jose Mourinho led them to a historic treble in the year previous, but much like their neighbours it has been a barren few year since. Milan have had 8 managers and Inter have had 10 – interestingly Leonardo having a stint at both – since the trophies dried up in desperate attempts to find a short term fix for a bigger club-wide problem. Like twins who seem to mimic each other’s movements and finish one another’s sentences, both Milan clubs lost a golden generation around the same time. Inter lost Javier Zanetti, Francesco Toldo, Marco Materazzi, Lucio, Walter Samuel, Dejan Stankovic and Diego Milito from their treble winning squad to either age or pastures new in 2010. New incumbent Rafa Benitez asked for the funds to replace the stalwarts but was rebuked. His resignation wasn’t. Milan, a mere 12 months later, won an 18th Scudetto and duly saw Andrea Pirlo, Christian Abbiati, Gennaro Gattuso, Mark van Bommel, Alessandro Nesta, Clarence Seedorf and Pippo Inzaghi depart. Pirlo, repulsed by the Milan hierarchy’s gall to only offer him a new 1-year deal, left for the Old Lady in Turin and pocketed 4 consecutive league titles as a response to Silvio Berlusconi et al.

Numerous attempts have been made to replace these all-conquering squads, but significant stumbling blocks were met. FFP regulations reared their fiscal head, as did inflated TV deals for the English, Spanish and German leagues. Being bankrolled by owners with an emotional attachment and a habit for overspending would no longer wash with the football authorities. The other European big boys got bigger, Juve broke away from the shackles of their publically owned stadium and joined the top table, and Milan stood still. The standing still soon became a culture that has become a plague to this once giant footballing city.

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If you examine Inter’s playing staff, it is undoubtedly talented. The new Chinese owners have put their hand in their pockets and begun to deliver on their promises of serious investment to compliment a squad that already had embers of ability. Mauro Icardi, wife-stealing and tattooing antics aside, is a footballer that you can conceivably see being amongst the post-Messi and Ronaldo generation and has 24 goals in 31 league appearances this season. He leads the line with a potency and directness that has earned him the captain’s armband. Gabriel Barbosa, Gabigol as he is known in his native Brazil, has yet to live up to his €30million price tag but certainly offers an alternative to Icardi. The now in his prime Ivan Perisic, Euro-spinning Joao Mario and versatile Antonio Candreva operate as a perfectly adequate foil behind Icardi. The midfield two will often consist of the now highly-rated and less much-maligned Geoffrey Kondogbia, and the high regarded energetic Roberto Gagliardini, on loan from Atalanta. Ever Banega and Marcelo Brozovic offer strength in depth that is difficult to match when you examine what is available to other Serie A sides.

Inter’s preferred starting 11 does look decidedly top-heavy, however. Centre back pairing of Miranda and Gary Medel – yes, the one that played for Cardiff – are on the wrong side of experienced and the back 4 is completed by a set of full-backs that are nothing to write home about. Despite an inability to keep the goal out at one end, this is a squad that should not be 7th in Serie A. Capitulation and under-achieving has become a culture at Inter. Virtually all memory of the brilliance of that 2010 treble winning side has been erased by 7 years of treachery, failure and disaster. Particular highlights include the recent 5-4 defeat at the hands of Fiorentina after leading 2-1 and surrendering a 2 goal lead in the Milan derby conceding in the 83rd and 97th minute – and that’s just their last two fixtures. Add in a shocking defeat at Crotone and another submission after leading at home to Sampdoria, it is clear that April 2017 has become an all too disappointing representation of Inter’s woes.

The complications at Milan are slightly different. The days of Zlatan Ibrahimovic being Zlatan, Kaka in his prime and Andrea Pirlo prowling around are well and truly gone. Star names are no longer the norm and those that appear to fit that bill are often too long in the tooth. Quick fixes in the form of club legends Leonardo, Clarence Seedorf and Pippo Inzaghi have come and gone disenchanted with the club’s hap-hazard approach to coveting success. As with a majority of quick fixes in football, success has miraculously not been an outcome. It has done more harm than good and left the club with a dependence on a young and raw squad mixed with distinct mediocrity. 18-year-old goalkeeping prodigy Gianluigi Donnarumma, attacking full-back Davide Calabria and elegant teenage midfielder Manuel Locatelli all represent a bright future if nurtured correctly. That is a sizable if.

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There’s also the all too common problem of being tempted away by any English, Spanish or German counterparts to contend with. Alessio Romagnoli, Giancomo Bonaventura and Mattia De Sciglio are also players of obvious quality – although the latter is currently subject of an increasingly nasty want away saga – that form a respectable core. Those around them are not of the expected Milan standard, however. Milan has become a stepping stone, or worse, a harbour for half decent footballers, and not the European elite they once enticed. Andrea Poli is certainly no replacement for Andrea Pirlo. They are also far too dependent on perma-Chinese-transfer-target Carlos Bacca for goals, with no-one else in the squad nearing double figures in late April.

The scale of Milan’s troughs have not been as pronounced nor as dramatic as Inter’s, but they are still as damaging. Consistent defeats to the likes of Napoli and Roma, direct rivals for the right to challenge Juve’s dominance, ensure a systematic and sustained policy of one step forward and two steps back for the Rossoneri.

So famous for its stylish footwear, Milan has two tattered pairs of crocs for football clubs. Nonetheless, with both clubs under new Chinese ownership, the Suning Holdings Group (Inter) and Yonghong Li (Milan), there is undoubted potential and hope for both outfits. To realise this, certain perceptions need to be dropped by both clubs at every single turn; from board to casual fan. History is not everything, neither is a half-full San Siro. Those illustrious stripes on each kit do not entitle either club to a God-given right to superiority. The sooner both clubs start again afresh, the sooner we may see them back in the proverbial big-time.

Greg can be found on Twitter @gregkitchin and on the Man on the Post podcast