Combined XI: Donnarumma, Bonucci the only players worthy of Gattuso's Milan generation
Montella paid the price for failing to get the best out of a squad that underwent an expensive transformation in the off-season.
But despite the significant outlays made by the club's new Chinese owners, picking a combined XI from the players Gattuso shared the field with in the 2003 Champions League final and the group he will have at his disposal this season lays bare the extent of the club's sad decline.
The slowing down of Silvio Berlusconi's glittering tenure as owner, heralded by the departure of Thiago Silva, Zlatan Ibrahimovic and Andrea Pirlo after the most recent Scudetto success in 2011, has left the team, once perennial challengers for domestic and European honours, struggling to achieve regular Europa League qualification.
And Gattuso, with limited experience of coaching at the highest level but boasting an impressive CV on the field for club and country, may not be impressed by the quality on display in first-team training at Milanello this week.
Goal of the Day
A special goal on a special day for Rino Gattuso
Un gol speciale per una giornata speciale! pic.twitter.com/LpKSLFmS4z
— AC Milan (@acmilan) November 28, 2017
Goalkeeper: Gianluigi Donnarumma
Between the posts is one of the few areas of the field in which the current squad have a player worthy of their predecessors.
Gattuso's team-mate Dida proved to be a stalwart for Milan and Brazil, winning Serie A, the Champions League twice and the World Cup.
But he was not always flawless and certainly benefited from playing behind an immensely assured backline.
Incumbent Donnarumma, heralded as the heir to Gianluigi Buffon, could yet prove superior to Dida.
It remains to be seen, though, if he can match the ex-Selecao star's trophy haul in black and red, should he opt to remain at Milan.
Defence: Alessandro Costacurta, Alessandro Nesta, Leonardo Bonucci, Paolo Maldini
Only one member of the present Milan defence is arguably equipped to play alongside the greats who proved so obdurate in previous decades.
And given his shaky form so far this season, Leonardo Bonucci's inclusion in our combined back four can be considered generous.
It is Bonucci's previous exploits with Juventus and Italy that have earned him a spot alongside Alessandro Costacurta, Alessandro Nesta and Paolo Maldini, with 2003 Champions League winner Kakha Kaladze the man unfortunate to miss out.
Gattuso will hope to get more out of seven-time Scudetto winner Bonucci than Montella did early this season.
Milan were crowned champions of Europe #OnThisDay in 2003 #UCLfinal pic.twitter.com/lViPwnr6f0
— #TeamOfTheYear (@ChampionsLeague) May 28, 2015
Midfield: Gennaro Gattuso, Andrea Pirlo, Clarence Seedorf
Hakan Calhanoglu, Lucas Biglia and Franck Kessie all arrived at San Siro ahead of the 2017-18 campaign, but none of Milan's current midfielders would be able to win a place in the starting XI ahead of the peerless trio named from kick-off against Juventus at Old Trafford 14 years ago.
The new coach Gattuso provided the snarling, biting foundation for Pirlo to pull the strings with such effortless grace.
Clarence Seedorf should not forgotten either, the former Netherlands international delivered a highly effective combination of physicality, skill and versatility that saw him win the Champions League twice with Milan and once at Real Madrid.
Attack: Rui Costa, Andriy Shevchenko, Filippo Inzaghi
It's the same story in the final third.
Homegrown striker Patrick Cutrone is winning over the Rossoneri faithful and Andre Silva - yet to score in Serie A - may still justify the considerable fee that secured his services from Porto.
But none of Milan's contemporary attacking options, which also include Nikola Kalinic, Suso and Fabio Borini, have any hope of living up to sparkling playmaker Rui Costa, poacher extraordinaire Filippo Inzaghi or Ballon d'Or winner Andriy Shevchenko, who was arguably the most dangerous striker in the world during the time he shared a dressing room with Gattuso.
Happy 40th birthday, AC Milan legend 2003 #UCL winner Andriy Schevchenko! pic.twitter.com/p4YhJg5uZ8
— #TeamOfTheYear (@ChampionsLeague) September 29, 2016