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#4 Unsettlement of key players
Tottenham has been under the chairmanship of Daniel Levy since 2002, in that time, the club has made solid improvements, with Levy having earned a reputation of being a tough negotiator, getting maximum value for players the club sells, while achieving success on a relatively shoe-string (by today's football standards) budget.
The club has a very frugal financial policy which is followed to the letter, and while it steadily ensures Tottenham are run on a profit unlike most of its rivals, it also means that the club is not as competitive in the transfer market as said rivals, with the club unable or rather unwilling to cough out the requisite funds to sign top quality players.
Another drawback of the club's fiscal policy is that their wage-cap limit stops the club from rewarding its players with contracts which their immense talents deserve, and always puts their top players at an earning disadvantage compared to their peers at other clubs.
Kyle Walker left the club at the start of last season, and earns double his Spurs salary at Manchester City, while Danny Rose complained publicly about not earning what he deserves, and was frozen out of the first team.
The latest player to decry the club's payment structure is Toby Alderweireld, who has just one year left on his current deal, and turned down a contract extension last season as the club refused to meet his wage demands of £180,000/week (which is fairly justifiable, as he is one of the top defenders in the league, and players inferior to his talent earn similar amounts elsewhere). The result of this is that he is being heavily linked with a transfer to Manchester United.
Tottenham has one of the most talented pool of players in the Premier League, and on their day, they can hold their own against any team anywhere in the world, but Tottenham's strict financial policies puts the club at risk of having a bunch of disgruntled players in their ranks, and this does no team any good in its pursuit of meeting its season's challenges.
