AC Milan offer a cautionary tale of what the future might bring for Arsenal
What once would have been considered a European glamour tie, Arsenal vs AC Milan will serve to showcase just how far great clubs can fall.
Arsenal are not in a good place right now. They're on their worst run of form in years, possess a perennially unhappy fan base, a manager resembling Futurama's Professor Farnsworth more and more every day and a group of players which one could most politely described as "not fit to wear the shirt".
Despite increased investment and theoretically brilliant signings like Pierre-Emerick Aubameyang and Alexandre Lacazette, the club's failure to strengthen problem positions and its willingness to allow a culture of mediocrity to foster has meant that things are now so bad that their current plight makes the last five years look successful by comparison.
This season's Europa League campaign has been a rude awakening for Arsene Wenger's team, but it should also put things into perspective. For if Arsenal want to see what true demise looks like - and what their own future might hold - they need look no further than their opponents at the San Siro on Thursday night.
It is testament to their past glories and the place they hold in the hearts of football fans that AC Milan are still considered by many to be football royalty, but the Milanese side's fall from grace has been a brutal one.
Champions League winners as recently as 11 years ago, the side which over the years boasted the likes of Marco van Basten, Frank Rijkaard, Paulo Maldini and Kaka is now a shadow of itself; ravaged by mismanagement, poor decision making and burdened by past glories.
The last nine years alone have seen nine managers in the hot seat, and has seen the club go from being regular Champions League finalists to just about scraping to qualify for the Europa League.
Admittedly, the reasons for Milan's decline differ from those of Arsenal. The Italian club amassed enormous debts during its glory days of the 2000s, all the while possessing a squad which, while talented, could quite convincingly have competed on the senior circuit.
Their subsequent inability to replace ageing players of class with anyone of even remotely similar quality led to a slide down the table, with their last four league campaigns seeing them finish as low as 10th and no higher than last season's 6th.
Last summer's Chinese takeover followed by an enormous outlay on transfers has offered a glimmer of hope, though even it has proved to be a potentially poison chalice, with their many signings - big names they may be - proving that the club's problems go beyond the quality of players on the pitch.
Meanwhile, question marks over the sustainability of investment and unrealistically high expectations remain and have led to a lack of patience from the owners and worries from supporters over the long term stability of the ownership model.
Such financial qualms are thankfully not something which Arsenal has to worry about, though they too have seen great sides retire and be replaced by players who - almost to a man - are not fit to lace the boots of their predecessors.
Despite the differences, there are still lessons to be learned, especially in what not to do in a bid to arrest decline. Throughout Wenger's recent years of troubles many former Arsenal players have spoken up about their own desire to help the club, with Thierry Henry going so far as to that he wouldn't "back down from a challenge" when asked if a potential vacancy at the Emirates would interest him.
Milan's recent managerial history, which has seen all but two of their last seven managers come from former players, suggests that the desire to right wrongs by hiring someone whose main attribute is knowing everyone's nickname is, at best, naivety and, at worst, incredibly foolish.
It also showcases what can happen to a club when a bad situation is allowed to cultivate over an extended period, rather than be snuffed out at the source, and that however good or bad things may be at a club - however breathtaking or mediocre a team's current phase may feel - they can always get much, much worse.
Despite the grim possibilities, Milan's failings also offer hope for Arsenal. While they face each other in the same competition, the Premier League club's decline has not been near as pronounced as their opponents, and they possess the resources to alter their trajectory from its current path.
That though, will rely on good decision making, something which hasn't been Arsenal's forte for quite a long time.
Succeed and this period in the club's history will be little more than a blip.
Fail to do so however and things could get immeasurably worse. Milan's history, more than most clubs, is evidence of that.