On the back of two strong Premier League campaigns, Tottenham Hotspur have allowed other teams to build squads that match or supersede theirs, while they've remained inactive during the transfer window. They have a good side with players who genuinely seem to care about the club and love playing for the manager, but the teams around them have bridged the gap in terms of quality, while Daniel Levy has kept his chequebook in his pocket.
So the last thing Spurs needed is for one of their better and more passionate players to give an interview with a tabloid criticising the club for a lack of spending, claiming he isn't paid what he deserves and is open to a move elsewhere. Step forward Danny Rose.
The timing of the left-back's interview, just days before the opening game of the season, couldn't be any worse. While many fans may agree with his point about the disappointment surrounding a lack of top signings, that doesn't mean they will welcome one of their players publicly attacking the club and putting himself in the shop window.
If Spurs are able to replace him, with a player like Luke Shaw for example, this may soften the blow of his departure, but if won't ease the frustration of losing a top player.
Under Mauricio Pochettino, Rose has been a player reborn, but he seems to harbour some resentment towards the fan base for the seasons before he became the best in his position in the league. He wasn't a popular figure before the arrival of their current manager and the supporters voiced their frustration when he was offered a new contract three years ago. Social media came alive with rants and memes mocking the club's decision to give Rose a new five-year deal.
"I will never forget some of the things Spurs fans were saying about me," Rose claimed this week. Maybe this interview is his revenge.
Having just turned 27, Rose is well aware he doesn't have many years ahead of him, at least not as a player who could contribute heavily to the success of his team, and maybe the lack of signings has convinced him Spurs won't be winning silverware any time soon. That mentality certainly won't be welcomed at the club so it wouldn't be a huge surprise to see Pochettino and Levy sanction a transfer. At the right price, of course.
But where would he go? Rose seems to have planned it out already. He's going to the north. No, not because United or Manchester City could treble his wages but because he wants to be closer to his mum.
With Manchester City having just spent £50 million on French left-back Benjamin Mendy, as part of their total spending of £220m this summer, it is unlikely that Pep Guardiola will be allowed to buy any more defenders.
Manchester United may be in the market, although Shaw has been earmarked for the left-back position.
However, Shaw's fitness and mentality is apparently a big concern for Jose Mourinho, who had previously tried to lure the youngster to Chelsea when he was their manager but lost out to United. The player clearly has bags of potential but people have been saying that for years and, other than the opening month of 2015-16 season, we've yet to see him justify his place at United.
He came to the club overweight, later admitting that he "took it a little bit easy" that summer, with both Louis van Gaal and then England manager Roy Hodgson questioning his attitude.
Confessions like that set alarm bells ringing. A teenager gets a transfer to Manchester United but doesn't work himself to death in preparation for the season ahead? In fact, he takes his foot off the pedal. You can't imagine Gary Neville behaving in such a way, even if his his natural ability was arguably inferior to Shaw's. There is a standard required at United, a work ethic, and however he may now protest to possess it, it doesn't appear as though Mourinho is convinced.
Many United fans will want Shaw to have one last crack of the whip after being very impressed by his performances in the month in the lead up to the horrible injury against PSV. If he could rediscover that form and play that way consistently, United have their left-back for the next decade. But it's hard to know whether Mourinho will be prepared to take a risk on a player who only looked brilliant for a few weeks two years ago.
The manager has publicly criticised Shaw on a number of occasions, clearly willing the player to come back with a reaction, but repeated injuries have made that difficult.
If United were to think in the short-term, and of winning the Premier League in the season ahead, then Rose would be starting for them at left-back. He attacks as well as he defends, like Shaw, is positionally sound, can cross the ball well and his pace would be a huge asset. Imagine Rose playing behind the likes of Marcus Rashford or Anthony Martial. United's left wing would rip defenders apart.
As appealing as that may be for United, Spurs would likely be happy to swap a wantaway player for someone five years younger. A deal that involved Shaw going in the opposite direction would suit them.
Although it may be a case of out of the frying pan and in to the fire for United, as Rose's injury record is poor too.
He's never played more than 28 Premier League games in a season and the most appearances he's ever made in all completions is 34. When you consider that almost 20 players at United made more appearances than that last season, it highlights the demands on players at clubs winning trophies with a heavy fixture schedule.
Rose is currently recovering from an injury that has seen him out of action since January and there are no guarantees he will come back soon enough or in top form.
While on balance it probably makes more sense for United to cling on to their 22-year-old injury prone left-back instead of swapping him for an older model, there is the nagging feeling that Rose offers so much more in terms of his mentality than Shaw.
Rose has been a warrior on the pitch for Spurs, fighting against the criticism from the stands to establish himself as a top player who gives his all on the pitch. He's certainly more of a Mourinho player than Shaw will likely ever be.
Both scenarios, whether relying on Shaw or forking out for Rose, involve more risk than Mourinho will be comfortable with though. United fans wouldn't be overjoyed to see Shaw fulfil his potential elsewhere and one day oust Rose from being first choice for England either.
Rose wants trophies though and Mourinho is better equipped than most to help him achieve that dream. Whether Mourinho views Rose as a safer pair of hands than Shaw, in United's bid to win the title, is yet to be seen though.