Not having a manager, contract negotiations for players being up in the air, and indecision over holding on to an asset like Harry Kane would be enough to ring the alarm bells at most Premier League teams, but those problems just form the tip of the iceberg for Tottenham Hotspur.
There's also the matter of the European Super League (ESL) saga, Jose Mourinho's sacking, another trophyless season, growing fan distrust, and the Tottenham Hotspur Trust Association calling for the resignation of the executive board.
As things stand, all the big decisions are on the table for Spurs chairman Daniel Levy, and it's anyone's guess what the team will look like come this summer and beyond.
What is going on at Spurs?
It feels like the end of the cycle for Tottenham, just as it felt when they lost their Champions League final in Madrid. Mauricio Pochettino was sacked at the expense of Mourinho, and 'ready-to-win first-team players' were signed. Everything was being done in an effort to finally get the club over the line and win their first trophy in a very long time.
It looked as if Spurs had changed their strategy; from no longer building with a long-term plan to winning as soon as possible. Everything started to fall into place; fans were happy, players were delighted, as were Levy and Mourinho. The club seemed to be heading in the right direction.
Enter 2021. Enter Everton. Enter Dinamo Zagreb. Enter ESL.
All the pieces have since fallen out of place. Spurs' short-term strategy to win a trophy has failed. Anyone watching them play in the final on Sunday would have agreed that they looked like a team that was inching further and further away from getting into the top 4, let alone winning a trophy.
What's next for Spurs?
So where does one of the self-appointed "Super League" clubs go from here?
To be fair to Levy, fate hasn't favored him much either, with their brand new stadium being a prime example. It was built on hopes that fans would fill it up week-in, week-out. Stadium tours were planned, and even the NFL was expected to feature at the venue, but all that has gone for a toss, thanks to Covid.
Like all other teams, Spurs have also been impacted by the pandemic, but the North London club have been hit harder, given their massive investment in the stadium with virtually no return on investment so far.
There's no doubt that the team needs new players, new faces, new legs on the ground. The likes of Eric Dier, Harry Winks, Harry Kane, Gareth Bale, Son Heung-Min and Delle Ali, among others, have question marks hanging over their futures.
This is not the same Spurs team that it was a few years ago. The idea that a new manager could sweep in, maybe get the best out of these players and push the likes of Manchester City, Manchester United and Chelsea for the Premier League title is now out of the question.
It's time for the club to rethink its priorities, goals, expectations and visions for the future.
If they are going to rebuild their squad, it would require more investment. But where is the money going to come from? Not to mention the payouts the club paid to their last two managers, Pochettino and Mourinho.
One option is to sell Harry Kane but that is a big decision to make. The fans wouldn't want to see him leave and neither would Levy. Also, are there any clubs in the current market that could afford Kane? We all know that when it comes to negotiations, Levy is a tough nut to crack.
It could be argued that should City and United fail to sign Erling Haaland or Kylian Mbappe, Kane could be the next best option. While those teams are not Spurs' direct rivals at the moment, how open would Levy be to selling to them regardless?
The new Spurs manager will have a lot on his plate, with not much money to spend. Brendan Rodgers has no interest in moving clubs, and Julian Nagelsmann has joined Bayern Munich on a five-year contract starting this summer.
That leaves Levy with not a lot of options to choose from. It's also fair to say that Spurs will be looking for a free agent rather than paying compensation to another club.
Questions also need to be addressed regarding their academy players and players out on loan, but until Spurs get a new manager and set their expectations, those players' futures are also up in the air.
As things stand, even a top 4 finish would be a remarkable achievement but sixth or seventh looks to be a more realistic result, and that should be their goal for a year or two, or even three.
With huge decisions to make and minimal margins of error from here on, the ball is squarely in Levy's court.