AC Milan's never-ending nightmare drags on with Champions League failure

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It was hoped that Leonardo, Gennaro Gattuso and Paolo Maldini could bring the glory days back to San Siro but they are all now facing the sack

For five minutes on Sunday evening, AC Milan were in dreamland.

Leading 3-2 at SPAL, the Rossoneri had moved above bitter rivals Inter into Serie A's fourth and final Champions League place thanks to Empoli's surprise equaliser against the Nerazzurri at San Siro.

Then, Radja Nainggolan's 81st-minute strike changed everything.

Despite Empoli's brave bid to level matters – and save themselves from relegation in the process – Inter held on, surviving a succession of near-misses, the most remarkable of which saw Danilo D'Ambrosio divert a cross against his own crossbar.

As the Nerazzurri's players celebrated one of the most dramatic finales to a season in Serie A history, their Milan counterparts were left crestfallen in Ferrara. They had won their final four games of the season yet it felt like it was all for nothing.

Even their coach, Gennaro Gattuso, a renowned hard-man, admitted: "I slept very little in the last few days and now, mentally, I'm in pieces."

It wasn't supposed to end like this. Paolo Maldini's long-awaited return to Milan last August was meant to herald the dawn of an exciting new era for the Rossoneri, after one of the darkest periods in their entire history.

After the chaos and constant uncertainty of the tenure of Rossoneri Sport Investment Lux., American hedge fund Elliot Management had turned to club men to restore order and stability.

"The beautiful thing about today is that we now have myself, Paolo and Gennaro in the sporting sector of the club," Leonardo enthused ahead of the start of the 2018-19 season.

With the Brazilian serving as sporting director, Maldini working alongside him as sporting strategy & development director, and Gattuso continuing in his role as head coach, Milan had tasked three former Rossoneri team-mates with reawakening one of the traditional giants of the global game.

However, this veritable dream team has been unable to drag the seven-time European Cup winners out of a seemingly never-ending nightmare.

It is now eight years since their last Scudetto; five since they last competed in the Champions League.

The latter drought is killing the club.

Deloitte Milan PS

In desperate times such as these for Italian football in general, qualification for Europe's premier competition has never been so important.

It's estimated that Champions League football would have guaranteed Milan an estimated €50 million in additional revenue next season, a significant sum of money for a club that ranked 18th in this year's Deloitte Football Money League – which ranks the game's highest earners – below the likes of Schalke and Everton.

The Europa League, by contrast, offers €20m at most, with the television market pool share a determining factor.

Of course, while Milan have finished fifth, there's no guarantee that they will even be allowed to compete in continental competition next season.

With the threat of further sanctions hanging over them for failing to meet Financial Fair Play (FFP) targets, the Rossoneri – who were originally banned from competing in last season's Europa League before launching a successful appeal – are now reportedly willing to cut a deal with UEFA that would see them excluded from this season's competition.

The thinking is that having failed to meet their primary objection (Champions League qualification) they may as well take the hit of going a season without European football, using that time in exile to try to balance their books.

It is a risky ploy, of course. The only reason Milan made it back into last year's Football Money League was their run to the last 16 of the Europa League, which played a significant role in their 8 per cent increase in revenue in 2017-18.

European football is that influential for Serie A clubs, given how far they have fallen behind their Spanish and English rivals in terms of commercial revenue and the value of TV rights deals.

Ivan Gazidis Leonardo Paolo Maldini - Milan

As Deloitte noted earlier this year, "The latest domestic broadcast rights sales process delivered an increase of just three per cent for the three-year cycle that commenced with Sky Italia and DAZN in 2018-19...

"Despite the commencement of a new international rights cycle, delivering an increase of 81% on the previous reported minimum guarantees, distributions to Serie A clubs will see limited growth until at least the next cycle beginning in 2021/22.

"Therefore, further revenue increases for Italian clubs will depend on a club’s ability to deliver growth in matchday and commercial revenue streams, as well as success in UEFA competitions."

Without Champions League football – or, worse again, any European football at all – Milan are going to be hit hard.

Leonardo even admitted earlier in the season that the club's summer transfer plans would be determined by their final Serie A standing.

"If this Milan finishes fourth, then we will have a major window in June," the former Brazil international explained.

"However, if the club's goals are not met, there will be no major signings and the current players on big deals will not be retained."

Leonardo AC Milan PS

His services are unlikely to be retained either, though, and Maldini's position is also at risk.

Milan have quickly lost faith in both and new Chief Executive Ivan Gazidis, who arrived in December after quitting Arsenal in September, is planning to completely overhaul the club's sporting staff.

However, Gattuso, who has for so long seemed like a dead man walking, there is still an outside chance he could be granted a stay of execution, given the dearth of proven, top-quality alternatives.

The former midfielder has admitted his frustration at the fact that Milan had their Champions League destiny in their hands for so long – thanks in no small part to a 10-game unbeaten run earlier this year – only to throw it away by winning just one of the six games that followed their demoralising derby defeat on March 17. Indeed, the Rossoneri were in the top four until losing at Torino in week 34.

However, he maintains that, taking the season as a whole, he did a good job with the players at his disposal. Crucially, Gazidis agrees.

"Despite the victory [over SPAL]," Gazidis commented, "we're quite disappointed at having failed to qualify for the Champions League.

"However, the team fought hard right until the end and I want to thank them for their efforts in overcoming the difficulties we had in terms of injuries and other setbacks."

Whether Gattuso gets to keep his job remains to be seen but Gazidis does, at least, enjoy a good rapport with Gattuso, who is nothing if not admirably honest.

The former Arsenal man also believes that Leonardo botched Milan's transfer market last summer, when the likes of Diego Laxalt, Samu Castillejo and Gonzalo Higuain arrived at the Giuseppe Meazza..

Consequently, despite the successful January additions of Lucas Paqueta and Krzysztof Piatek, Gazidis and the World Cup winner have never quite seen eye to eye, which is why Leonardo is now likely to take up a job with the Brazilian Football Confederation (CBF) and be replaced at Milanello by Lille sporting director Luis Ocampos.

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Given their financial limitations, Gazidis believes that Milan must now focus on youth and unearthing rough diamonds – areas in which Ocampos excels.

In short, Milan plan to start over. Again.

This sleeping giant remains trapped in a seemingly never-ending nightmare.

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