When Milan Coach Vincenzo Montella takes his place on the Olimpico bench on Monday night, Romanisti may reflect that he could easily have been sitting in the other dugout. A club legend during his time as a player and already working with the youth system, it looked for all the world that it was Montella’s destiny to one day take the helm, but the capital club repeatedly allowed him to slip through their fingers.
The former striker had a brief caretaker spell on the Giallorossi bench in 2011, replacing Claudio Ranieri and steadying the ship for a sixth-place finish. It was generally agreed that L’Aeroplanino had done a decent job, but he wasn’t given the opportunity on a permanent basis.
Instead of sticking with Montella - a Scudetto winner with the Lupi in his playing career - Roma went for a ‘flavour of the month’ appointment, in the shape of Barcelona B Coach Luis Enrique. He may be a Champions League winner now, but Enrique was a poor fit at the time, imposing a sterile possession game which brought only seventh-place.
Montella, meanwhile, was building his reputation. Just days after being told he was no longer required at Roma, the Coach was appointed at Catania. The faith shown by the Elefanti would be rewarded, with Montella leading the unfancied Sicilian side to mid-table.
Once again, the young tactician was linked with a return to the Eternal City, but once again Roma decided to look elsewhere. Rather than put their trust in the hands of the inexperienced but promising Montella, the Giallorossi opted for a return to the past in the shape of Zdenek Zeman, with predictably trophyless results. Days after Zeman was confirmed at Roma, Montella moved to Fiorentina.
It was in Florence that Montella truly started to shine, bringing an attacking possession game to the Viola. The Tuscan side had finished a lowly 13th in the 2011-12 season, but Montella’s revolution brought fourth place for three seasons in a row, as well as a Coppa Italia Final and a Europa League semi. However, after publicly bemoaning the board’s lack of ambition (sound familiar, Paulo Sousa?), Montella was sacked at the end of his third season.
Following a brief spell amid the chaos at Sampdoria, Montella was given the Milan job this summer. A poisoned chalice to many before him, the Coach is making a success of the Rossoneri. Despite a lack of investment in the summer, Montella’s side are just four points off the top of Serie A, level with Roma. Taking largely the same squad which failed his predecessors and adding some raw youngsters, the 42-year-old has the Diavolo looking truly dangerous once again.
His opposite number on Monday night, Luciano Spalletti, is only under contract until the end of the season, and it’s far from certain he’ll renew. Should he walk away in June, Roma could be looking for their sixth Coach since Montella was allowed to leave.
As the writer of any hackneyed rom-com could have told them, they had the right man under their nose the whole time.