Sergio Conceicao’s AC Milan reign began with him puffing on a celebratory cigar after they beat Inter Milan to win the Italian Supercup in Riyadh.

Dancing to tunes blaring out of a speaker, the Portuguese looked like a man oozing confidence after lifting his first trophy less than a week into his new job.

Conceicao, as the kids would say, had aura.

But since the celebrations in Saudi Arabia, it is Milan’s season that has gone up in smoke. 

Pictures of Conceicao with his cigar resurfaced online on Wednesday night after the Rossoneri lost the Coppa Italia final to Bologna. Suffice to say, it was not Milan fans who shared them.

The 1-0 defeat in Rome felt like a fitting finale to a dismal season, which may well leave Il Diavolo out of European competition altogether.

Eighth in Serie A with 60 points, the real race for the Champions League is taking place way ahead of them and Milan’s most likely destination if they win their last two games is the Europa Conference League

Whether they would want that is another matter. For a club with seven European Cups in the cabinet, the prospect of playing in the third tier of continental football feels like a punishment.

But this version of Milan, the Milan of RedBird and Gerry Cardinale, bears no resemblance to the Milan that dominated at home and abroad for decades.

In a season strewn with disappointments, Bologna was the meekest of defeats. The Rossoneri had just two shots on goal despite churning through three strikers – Luka Jovic, Santiago Gimenez and Tammy Abraham –  in 90 minutes.

So often Milan’s saviours season, Christian Pulisic and Tijjani Reijnders for once could not drag their team out of trouble. Rafael Leao was again at his frustrating best, a bright start but soon fading. 

The contrast with Bologna could not have been starker and the gap between the two off the pitch is wider still.

Celebrating a first trophy in 51 years, the Rossoblu are going places under Vincenzo Italiano whose footballing philosophy has found the perfect foil in Bologna’s ambitions.

Conversely, under Conceicao, Milan are going nowhere. Out of the Champions League, beaten in the Coppa Italia final and eighth in Serie A, the Supercup triumph in January is nothing but a distant memory.

“I feel for the fans, it’s a real blow for everyone, we should have done better,” he said in the bowels of the Stadio Olimpico.

“Right now, I’m just trying to figure out what went wrong today. We need to see out the season with some pride, and then we can have a proper chat about it.”

Conceicao has won 15 of his 29 matches in charge in all competitions, losing nine and drawing five. In Serie A, his record reads 10 wins, six losses and three draws at an average of 1.74 points per match.

His record is only marginally better than Paulo Fonseca, who won seven of his 17 Serie A matches, losing four and drawing six at an average of 1.59 points per game.

Under Conceicao, Milan have scored 32 goals and conceded 23 in 19 league fixtures , while they netted 26 and allowed 17 in two fewer games under his predecessor. They were eighth when Fonseca was sacked and they are eighth now.

And yet, Conceicao seemingly retains Milan’s trust, with technical director Geoffrey Moncada insisting the board had “total faith” in him.

Not that the Portuguese should be held responsible for the decline of a club that, lest we forget, celebrated a 19th title just three years ago.

The bulk of the blame lies squarely at RedBird’s door. Since the American private equity firm took control in August 2022, chaos has reigned supreme at the San Siro.

Parting ways with Stefano Pioli, who led Milan to their last Scudetto, in favour of Fonseca was a gamble that never looked like coming off. Milan’s apparent refusal to entertain the idea of bringing Antonio Conte in was telling of their vision.

A proven winner who would have fit seamlessly in Silvio Berlusconi’s Milan, the 55-year-old would have demanded signings and would have had no problem venting his frustrations in public. 

Conte is nobody’s fool, but as RedBird advisor Zlatan Ibrahimovic made clear in the summer “Milan needs a coach, not a manager”.

Similarly, RedBird’s Moneyball approach to signings has left more questions than answers. 

Balancing the books is crucial in the modern game, but a club of Milan’s history and pedigree cannot get on without breaking the €30m (£25m) barrier on signings for two years.

When Milan did spend, the returns on their investment were negligible.

Gimenez, signed from Feyenoord for a €30m fee plus bonuses in the winter window, has scored six goals in 18 appearances in all competitions, while fellow January signing Warren Bondo has played 164 minutes of football.

Joao Felix, meanwhile, has one goal in 19 appearances with only six starts to his name.

Milan fans have repeatedly questioned RedBird’s lack of ambition this season. The American consortium has held talks with Igli Tare to become sporting director but negotiations have moved at a glacial pace.

“The Coppa Italia final loss means Milan will have to make big calls,” Fabio Capello wrote in his column in La Gazzetta dello Sport on Thursday.

“The club has been dragging its feet for months, but that defeat in Rome leaves no room for debate. Milan can’t be this bad again next season; I hope the people in charge know that.”

The longer the uncertainty lingers, the longer Milan drift and the longer the road back to success will be.