Tottenham face Manchester United on Thursday in the caretaker charge of their third manager of the season, with open revolt among the fanbase and a risk of losing the club's greatest ever goalscorer.
A season to forget hit a new low on Sunday as Newcastle scored five times in the first 21 minutes of a 6-1 win that cost interim head coach Cristian Stellini his job.
Tottenham sit sixth in the Premier League, but have lost 10 of their last 22 games after a bright start to sink hopes of a return to the Champions League next season.
Stellini had only been in charge for four matches and his appointment was symptomatic of a club lacking in leadership on and off the field.
The Italian had been a long-serving assistant under Antonio Conte and was a baffling choice to step up once the former Chelsea boss' time in charge became untenable after publicly berating his players for throwing away a 3-1 lead to draw 3-3 at bottom-of-the-table Southampton last month.
The Spurs squad have offered to reimburse the match tickets of travelling fans to St. James' Park after a performance that chairman Daniel Levy branded "wholly unacceptable".
But it is Levy who is now receiving the bulk of the backlash from supporters for years of poor decision-making in the four years since the club reached its first Champions League final.
Levy can point to successes off the field in the club's state-of-the-art new stadium and training ground.
But he has overseen a 15-year trophy drought and every game at the glistening 63,000 capacity Tottenham Hotspur Stadium is now greeted with chants of "Daniel Levy, get out of our club!"
Former midfielder Ryan Mason has been ushered in to act as a temporary figurehead for the final six games of the season, just as he was two years ago when Tottenham sacked Jose Mourinho without having a replacement lined up.
Kane's future uncertain
Mourinho replaced the beloved Mauricio Pochettino, who was dismissed just months after reaching the Champions League final and years of overachievement given the budget afforded to the Argentine as money poured into building the £1.2 billion stadium ($1.5 billion).
To rub salt into Spurs fans' wounds, Pochettino now looks set to take over at rivals Chelsea just Levy embarks on another new manager search.
He will do so without a sporting director after Fabio Paratici resigned earlier this week when his appeal against a 30-month global ban, handed down by the Italian football federation for his role in a false accounting scandal at former club Juventus, failed.
But the most painful blow of all could be to come should Harry Kane, who turns 30 in July, decide he cannot afford to waste his few remaining prime years at his boyhood club.
Kane's goal to beat Manchester City in February and pass the legendary Jimmy Greaves as Spurs' all-time leading scorer in the process has been the highlight of a disappointing campaign.
Even surrounded by mediocrity, the England captain has scored 26 goals this season.
Kane previously tried to force an exit to Manchester City two years ago. Levy stood in his way back then, but the striker has more bargaining power now with only one year left on his contract amid interest from Manchester United and Bayern Munich.
Sunday's shellacking painted a bleak future for Spurs even without losing their star striker.
Newcastle look set to secure a top-four finish in their first full season under the ownership of the Saudi sovereign wealth fund.
More investment is expected to flood in to make the Magpies regular challengers for trophies, pushing Tottenham further down the food chain in the process.
Spurs cannot afford to lose Kane if they are to bounce back under a new manager next season.
But Levy, the businessman, may not be able to stomach the prospect of his biggest asset leaving for free in 12 months' time.
