Why AC Milan's Vincenzo Montella will be the most under pressure manager next season

Pep Guardiola, Jose Mourinho, Zinedine Zidane, Unai Emery and Antonio Conte. What do these managers have in common?

They are among the elite managers who will be under enormous pressure next season for a number of reasons. Nonetheless, there is one man not yet in their category who will be on the hottest seat of them all next season: Vincenzo Montella, the manager of AC Milan, will head into his second season in charge with lots of eyes on him.

AC Milan have had the most eye-catching transfer window so far and there is still over a month to go. The Rossoneri capped of what has been a very decisive summer so far with the best signing of all the big teams.

Their capture of Leonardo Bonnuci brings arguably the world’s best defender to the San Siro and weakens a major title rival, Juventus, in the process. That is not a move many expected from a team that has finished in 10th, 7th and 6th in the last three Serie A seasons. Another big win for the Italian giants came with the extension of  Gianluigi Donnarumma’s contract.

One major reason Montella will be under pressure is the presence of new ownership.

Milan’s former owner, Silvio Berlusconi, and a group spearheaded by Chinese businessman, Li Yonghong, finalized the long-awaited change of ownership. The new owners and their executives have wasted little time in making their mark.

Milan’s CEO, Marco Fassone, and sporting director, Massimo Mirabelli, have adopted an approach that would make many a Football Manager aficionado proud as they have almost assembled a new squad in one window. Bonucci is one of 11 new signings by the club so far this summer.

All this means Montella has plenty of expectations to live up to in the new season.

Milan’s new owners may focus on a return to the Champions League in public. However, privately they will surely be expecting more. The board, the fans and the footballing public will want to see how Milan performs after a summer of significant change. Montella did well with what he had last season, winning the Italian Supercup and leading the team back to Europe, but this is an entirely different challenge.

The former Fiorentina boss will have to integrate his new signings, almost all of whom will play a key role, while ensuring the continued progression of youngsters like Davide Calabria and Manuel Locatelli. The experience of winning silverware last season will help while Bonucci’s leadership and experience will be vital.

Montella will also be tasked with ensuring that arguably the best team he has had in his career plays stylish, winning football in homage to Milan’s history. Whether or not the expectations will be fair is another matter.

The most even-keeled fans will be satisfied with a strong run at silverware in all competitions and a return to the Champions League. Still, it is not unthinkable that this mixture of talent could do better if Montella makes the right decisions.

Juventus will still be favorites as they continue to add talent and retain the league’s best tactician in Massimiliano Allegri. The Old Lady may be preoccupied with Europe this season, though, considering their recent heartbreak on the continent.

The jury is out on the other two major contenders. Napoli played some scintillating football yet fell short in key moments while the boost in productivity from Edin Dzeko could only do so much for Roma. Both sides will feel some measure of confidence after Bonucci’s departure but they have previously failed to capitalize on any moments of weakness from Juventus.

The fact that these teams have the easier Champions League schedule to contend with does work against Milan but the growing list of additions should provide Montella with the depth to compete. There is the possibility of more to come, as well, with the transfer window over a month away from closing.

According to Italian outlet La Repubblica, as referenced by reputable Spanish publications AS and Marca, Atletico Madrid may look at the possibility of loaning Diego Costa to Milan for the first half of the season should they sign him from Chelsea this summer.

With Carlos Bacca likely to leave, as reported by ESPN, the Rossoneri still need a quality striker to lead their resurgence next season. Such a move would heap even more pressure on Montella to get results.

Milan’s season officially begins with a Europa League qualifying tie on July 27. That will give Montella more time to get any kinks out of his side and, hopefully, get the season off to a positive start. The positive performances for some of the new signings in the most recent friendly against Bayern will heighten expectations.

The question of when the two sleeping giants of Italian football, Milan and Inter, would rise again has been constant in the last few seasons. Milan’s actions this summer suggest that time may have come. Montella’s task will be to ensure that his side lives up to the hype created by this summer’s activity.