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This feature is part of The Masterminds: 10 Under 45

Vincenzo Montella is not entirely dissimilar to Roberto Mancini. Like the former Inter and Manchester City manager, Montella exudes effortless charisma and cool. There he was at Fiorentina, patrolling the touchline with a slim-fitted Viola gilet underneath his Dolce & Gabbana overcoat. Like fellow fashionista Mancini, Montella often opts for a scarf to tie his outfit together.

Watching him on the touchline, it’s easy to be impressed by his slick, Neapolitan look. His chiselled, almost gaunt facial features and exquisitely coiffed haircut carry with it a sense of quiet authority. However, while it’s easy to be distracted by how impressively designed and assembled his accoutrements are, his tactical nous and coaching philosophy are what earned him a place in this young Masterminds series.

It’s important to remember that, before you laugh off Montella’s potential to become one of Europe’s finest managers, this writer would happen to agree that the 42-year-old has plenty to learn. Yet there is compelling evidence to suggest that the former striker – affectionately dubbed L’Aeroplanino because of his famous celebration – has positioned himself on the right trajectory to perhaps one day stroll around the San Siro with the Scudetto, an accessory infinitely more eye-catching than an Armani watch.

Montella enjoyed a steadily impressive playing career which eventually saw him inducted into Roma’s Hall of Fame. During nine seasons at the Giallorossi, Montella won the Scudetto in 2001 when he spearheaded Fabio Capello’s attack that also boasted Gabriel Batistuta and Francesco Totti in its ranks. Montella contributed 14 goals that season, and his insatiable work-rate, which dwarfed that of his more illustrious team-mates, endeared him to Roma supporters.

Montella was always an intelligent poacher, trained in the Filippo Inzaghi school of thought. Deceptively quick and composed with the ball at his feet, Montella relished opportunities to sneak in behind defenders and finish off attacks with aplomb. Although he was embraced by the fans, Montella the player was never quite as stylish as Montella the manager.

After retiring in 2009, Montella was appointed as a coach for Roma’s Giovanissimi Nazionali (under-15 side), but it wasn’t long before he was tossed into the lion’s den. Claudio Ranieri had replaced Luciano Spalletti in 2009 and, while the Tinkerman galvanised a squad reeling from a horrendous start to the campaign to eventually finish second, it didn’t last. In Ranieri’s second season, Roma failed to win any of their first four Serie A games and never fully recovered. In February, they crumbled. A 5-3 defeat to Inter followed by a 2-0 home loss to Napoli put Ranieri on the brink – surrendering a 3-0 lead to lose 4-3 to Genoa pushed him over it.

After the Genoa game, the board accepted Ranieri’s resignation and Montella was named his replacement on an interim basis within 24 hours, placing him in charge until the end of the season. Montella was 36 and didn’t possess any coaching badges, but it was believed that this untouched enthusiasm for becoming a coach would act as an asset, rather than a defect.

Read  |  Fabio Capello and the legendary Milan years

A Roman defence lying in ruins greeted Montella’s arrival, having conceded 11 goals in their last three league matches. Yet Montella started off impressively, winning his first game in charge away at Bologna and keeping a clean sheet in the 1-0 win. Although he added victories against Lecce and Lazio in the Derby Della Capitale, he was unable to overturn a deficit to Shakhtar Donetsk in the Champions League last-16 and lost 2-1 on aggregate to Inter in the Coppa Itali semi-final to miss out on a shot at silverware in the final.

Montella remained popular with the fans and his players but, when it came to the end of the season, Roma consciously steered clear of sentimentality when they appointed Luis Enrique as Ranieri’s permanent successor. Montella certainly had reason to be disappointed but he was never given assurances over his future and did lack senior coaching experience.

However, Enrique – at that point – was also inexperienced, and his failure at the Stadio Olimpico was only made more painful by Montella’s success at Catania. It was then, during the 2011-12 campaign, that Montella established himself as an emerging tactician in Italian football. Ditched by Roma, Montella made the brave decision to join a club with a wage bill a quarter of the size of the Giallorossi’s.

It was also a studious decision, as Montella was aware of the potentially career-wrecking calamities that could have occurred at Roma with a young manager at the helm in a hotly-pressured environment, answering to a demanding board with grandiose ambitions. Instead, Montella chose not to complain about being losing to Enrique and joined Catania, where he was lauded for guiding the Sicilian minnows through an eight-game unbeaten streak, their longest in the Italian top-flight since the 1961-62 season.

At Catania, Montella brought the squad together. What the Rossazzurri lacked in financial muscle, they made up for in resilience, dogged perseverance and a sense of togetherness that allowed a never-say-die attitude to grow. Montella’s Catania weren’t always the most attractive team in the league but they possessed a remarkable spirit. Against Fiorentina, they recovered twice from Stefan Jovetić strikes to draw 2-2, before scoring an injury-time equaliser to draw 3-3 with Novara. In between those two results, Catania fought back from a goal down to shock Inter at the Stadio Massimino.

During his solitary campaign in Sicily, Montella was commended for transforming the fortunes of Marco Motta, an athletic and dynamic right-back whose Juventus career had suffered because of ill-discipline and a tendency to let concentration levels slip. Motta was loaned to Catania in January 2012 and enjoyed one of the most productive spells of his career working alongside Montella.

Motta was instantly taken with his new manager, offering particularly effusive praise about Montella’s style before he departed for Fiorentina: “I’ve always thought that his greatest strength is his ability to transmit calmness to the side and his power to get his players to express themselves at their best,” Motta said. “He’s able to do that because he was a great player himself, so he respects the needs of players at the highest level. He understands how a player can suffer dips in form over the course of a season, while he makes sure that everyone feels a part of the squad. He’s also meticulous in his preparation for games, where he tries to get the team to play his idea of football without being excessively worried about the opposition.”

Montella’s demeanour and preparedness were undoubtedly attractive attributes for Fiorentina, who turned to him after a tumultuous season that ended with a 13th-place finish in Serie A and the abrupt dismissal of Delio Rossi as head coach after he punched Adem Ljajić. There was to be no explosiveness or volcanic bursts of desperation from Montella’s calm disposition.

Read  |  The painful death of AC Fiorentina

Montella’s arrival coincided with a summer of upheaval at La Viola. No fewer than 17 players, including high-profile acquisitions like Alberto Aquilani and Borja Valero, were added to the squad, with Alessandro Gamberini, Riccardo Montolivo and Valon Behrami among the notable departures.

The Viola revolution, led by its effortlessly cool tactician, set about extinguishing the torment of the previous season in impressive fashion. While such widespread changes in personnel can easily result in chaos, Fiorentina instead proceeded to play some of the most attractive football on the continent as they came up agonisingly shy of Champions League qualification. From flirting somewhat with relegation at times in the previous season, Montella’s wind of change was a remarkable turnaround that further enhanced his burgeoning reputation in Serie A.

Montella implemented a versatile 3-5-2 system at the Artemio Franchi which yielded some thoroughly impressive results. Facundo Roncaglia, Stefan Savić and Gonzalo Rodríguez were deployed as the three-man defence, with Juan Cuadrado and Manuel Pasqual as wing-backs. With Cuadrado and Pasqual offering width and pace, La Viola became one of the most devastating counter-attacking sides in Serie A, a brand of football that became too hot to handle for several opponents.

At the San Siro, Fiorentina dominated Milan during an impressive 3-1 victory, a game that saw Montella shrewdly execute his tactical masterplan. Without Jovetić leading the line, Montella deployed Luca Toni as the lone striker with Ljajić in behind. With David Pizarro anchoring the midfield as the regista, Valero and Aquilani were unleashed to making runs into the attacking third from deep as the wing-backs occasionally tucked inside. Valero and Aquilani scored to give Fiorentina a 2-0 lead, ultimately beating the Rossoneri 3-1 in a technically accomplished performance that left Massimiliano Allegri scratching his head in bemusement.

Montella was also responsible for Ljajić’s revival during his first season in charge of Fiorentina. Siniša Mihajlović, the Serb’s previous coach at Fiorentina, had painted a withering picture of the playmaker’s attitude when he said he spent too much time eating Nutella and playing video games. Indeed, while there was no justification for Rossi lashing out at the Serbian in a moment of red mist that got him sacked, the player was in the wrong for sarcastically applauding the coach and giving a thumbs up after being substituted. It didn’t particularly lend itself to modesty and professionalism, but that would change – for the most part – under Montella.

Ljajić, dubbed ‘The Little Devil’, became one of Fiorentina’s key attacking components under Montella, scoring 11 goals and notching eight assists. However, while Montella looked forward to continuing his work with Ljajić with the view of making him one of Europe’s most effective attacking midfielders, his head was turned by Roma in summer 2013 when they earmarked him as the ideal candidate to replace Erik Lamela, who had left to join Tottenham Hotspur. After a summer-long transfer saga, Ljajić eventually signed for the Giallorossi, which was a blow to Montella after missing out on Champions League football with Fiorentina on the final day of the season.

Montella’s work at Fiorentina was certainly worthy of praise. He was brave enough to lead a mass overhaul in the club’s personnel and style of play, innovations which led to three consecutive fourth-placed finishes, the final of the Coppa Italia and the Europa League semi-finals. It may have been moderate success, but there certainly couldn’t have been much more expected from him when he was appointed as Rossi’s successor.

Read  |  The Masterminds series

Montella’s next adventure was a short-lived one, with Sampdoria. While he found the going tough at the Genoese club, AC Milan still believed he was the perfect candidate to take them forward after sacking Mihajlović in April. The Rossoneri finished seventh in Serie A, missing out on European football for the third season running. However, with Silvio Berlusconi finally agreeing to sell the club, it was time for a change at the San Siro, a new era that with Montella the young face leading it. Speaking of young, the club promised to focus on the development of academy players, a driving reason behind appointing Montella.

It must have been immensely for the supporters – and prospective new owners – to witness how thrillingly events unfolded against Sassuolo in October. Giacomo Bonaventura had fired the seven-time European champions ahead, only for their defence to fall to pieces as I Neroverdi roared back with three goals to lead 3-1. Such a capitulation was not indicative of Montella’s style, but the comeback that followed certainly was. Montella has the ability to instil in his players a resilience that allows them to respond strongly to adversity. After going 3-1 down to Sassuolo, they regrouped admirably, Carlos Bacca’s penalty setting up a rousing climax.

But what happened next was particularly pleasing for Montella and the fans. Thirteen minutes after replacing Montolivo, 18-year-old academy product Manuel Locatelli met a clearing header from a Sassuolo defender with a rocket launcher of a left-footed drive, ripping into the top corner to make it 3-3. Gabriel Paletta scored four minutes later to clinch a dramatic three points which, at the final whistle, left Locatelli – a player with Milan in his heart since he joined them at the age of 12 – shedding tears of joy. Locatelli fulfilled his dream that night against Sassuolo, and it was Montella who gave him the chance to stake his claim to be Milan’s creative force, and to replace the declining Montolivo.

Three weeks later, Locatelli did it again, serving up another stunning strike to beat Juventus. Milan’s starting line-up that night included fresh-faced talents like Gianluigi Donnarumma (Buffon’s 18-year-old heir apparent), Alessio Romagnoli, Mbaye Niang and Suso, confirming that the long-term future for the Rossoneri seems a great deal brighter than in previous seasons. The integration of youth players into the starting line-up, blending with the experience of campaigners like Ignazio Abate, Bonaventura and Carlos Bacca, has been a central part of Montella’s vision at Milan. He is building for the future, and he’s doing it steadily and competently, eliminating the possibility of chaos, a stark and welcome contrast to the erratic Mihajlović.

Bonaventura considered leaving Milan in the summer, but then he was struck by how confidently Montella arrived at the club and laid out his plans: “I was expecting to find more chaos, but Montella was very clever in isolating us from that,” said Bonaventura. “I thought he would show up and turn everything on its head, but instead he took it one step at a time and the thing that helped was keeping a calm atmosphere.”

Indeed, Montella believes in a philosophy in which cooler heads will prevail and, with a series of encouraging performances and results, it appears to be functioning efficiently. Montella’s first season at the helm with Milan has also given the manager his first major honour after beating Juventus in a penalty shoot-out to win the Supercoppa Italiana two days before Christmas. With that in the bank, Montella has a platform from which he can continue to develop his young team, strengthening a never-say-die attitude that has seen decisive goals against Lazio, Bologna, Cagliari, Crotone and Palermo coming after the 80th minute.

Yes, Montella has plenty to learn as a coach, but time is still very much on his side and, should be afforded it beyond the end of his first campaign, he has the nous, level-headedness and self-confidence to make Milan an Italian powerhouse again 

By Matt Gault    @MattGault11