This weekend promises to be an emotional one for Carlo Ancelotti. The very thought of it, he confessed last week, is "making my heart pound."
Ancelotti's home debut at the Stadio San Paolo with his new side Napoli comes against AC Milan, who are less like a club to him and more like a family. When Ancelotti left Milan nine years ago, the club liked to boast about being the most successful in the world when it came to the number of international trophies on show in their office. Ancelotti won the European Cup twice as a player (1989, 1990) and twice as a coach too (2003, 2007) in red and black. But an awful lot has changed since he departed in 2009.
While Ancelotti moved on to Chelsea and consolidated his place in the football pantheon with spells at Paris Saint-Germain, Real Madrid and Bayern Munich until 2017, Milan declined. Austerity began to bite and things started to spiral when club president Silvio Berlusconi considered Massimiliano Allegri to be underperforming when, in fact, their last Scudetto-winning coach was overachieving just by keeping the most mediocre Milan side in decades in the Champions League.
That was four years ago and Milan haven't qualified since, while Allegri has won the last four Scudetti with Juventus. This summer it looked like Milan had hit rock bottom when UEFA kicked them out of the Europa League and the Elliott hedge fund repossessed the club after Berlusconi's successor Li Yonghong defaulted on his debt. The night is darkest just before the dawn, however, and Milan now have a credibility about them that has been conspicuous by its absence for far too long.
Elliott's involvement helped get Milan reinstated into the Europa League on appeal and now there are a host of legends with close ties to the club helping it get back on its feet: Gennaro Gattuso as manager, Leonardo as general manager and Paolo Maldini ending his exile from the club he incarnates to join as the new sporting strategy and development director this month.
Ironically, one of the reasons Ancelotti gave for returning to Serie A this summer after almost a decade away was that he wanted to see old friends again. He will just have to do so in a very different context.
In Rome last Saturday for Napoli's season opener against Lazio at the Stadio Olimpico, Ancelotti bumped into Andriy Shevchenko, the star striker of his all-conquering AC Milan side, who was on the touchline in his new role as a pundit with DAZN. Simone Inzaghi, whose brother Pippo (also a Milan legend) cannot speak highly enough of Ancelotti, stood in the adjacent technical area hoping he wasn't about to be taught a lesson by the most successful Italian manager around.
Unfortunately for Simone, he was. Napoli came from behind to win 2-1 in a manner that exceeded expectations in light of their poor summer recruitment and dismal preseason form.
But while pundits have generally been quite down on Napoli -- downgrading them from title challengers to a team with a fight on its hands just to stay in the top four -- events in the Eternal City last weekend were a timely reminder of the need to show Ancelotti the respect his CV deserves.
For those Napoli fans still lamenting the failure to sign Karim Benzema or Edinson Cavani, decrying a lack of ambition from owner Aurelio de Laurentiis, the way to look at it is simple. Ancelotti was Napoli's big signing. "The biggest since Diego Maradona," according to Milan's former sporting director Ariedo Braida. You don't appoint someone who has won the Champions League three times and league titles in England, Italy, Germany and France unless you aspire to win something.
His decision to return to Italy is a major factor, combined with the arrival of Cristiano Ronaldo, in Serie A regenerating the interest and profile it had lost. Another is that Milan look and feel like Milan again.
Win, lose or draw one imagines Ancelotti and his old friends will share a glass of red wine after Saturday's game at the San Paolo where the atmosphere promises to be hot, not least because the reunions on the sidelines aren't the only ones this game has in store.
Pepe Reina could make his Milan debut after joining on a free transfer following his fall-out with De Laurentiis, which will likely ensure the former fan favourite gets a good reception from the Ultras who remain at odds with Napoli's president.
Then there is Gonzalo Higuain, a persona non grata in these parts ever since he left two years ago to join Juventus. Now at Milan on loan, El Pipita is the best striker to wear the No. 9 shirt at the club since Ancelotti had Pippo Inzaghi in his ranks and the Argentine's record against Napoli also goes a long way in explaining why the Partenopei are unwilling to forgive and forget his decision to walk out on them in 2016. Five goals in six games, including the winner for Juventus at the San Paolo last season, make for ominous reading ahead of what many anticipate to be the start of a season-long rivalry between these two clubs for a place in the top four.
Hopes that the return fixture might have a bearing on the title race, as was the case in May 1988, seem a little far-fetched. Milan left the San Paolo that day to the admiring applause of Napoli fans who recognised greatness when they saw it. That moment has always stayed with Ancelotti. And as with the standing ovation Ronaldo received after his picture perfect bicycle-kick goal at the Allianz Stadium in April, it helps us understand the move he made in the summer.
"That magical afternoon is when I really started cultivating my dream of working in the South," Ancelotti said at his unveiling. After a dream start last weekend, it'll be great to catch up with old mates. But Saturday's game won't be a friendly and Milan will have no problem gently waking him up.