It's fair to say that Erik ten Hag hasn't had the easiest start to life as Manchester United boss, with Cristiano Ronaldo now wanting to leave the club before even training with the Dutchman.
Ronaldo returned to United last summer, and finished as their top scorer last season in a dismal year for the club, the worst in their Premier League history. According to Manchester Evening News, Ronaldo wants to move elsewhere as not only has their failure to secure Champions League football been disappointing, but their slow start in the transfer window has worried the 37-year-old.
Reports have suggested that Ronaldo could be set for a shock move to Chelsea, with United accepting his desire to leave and a £14million bid being prepared by the Blues. If the deal goes through, it will show that things have come full circle for United, after being on the opposite end to Arsene Wenger's problem at Arsenal ten years ago.
Wanting to win trophies, play competitive Champions League football and not being convinced about the direction the club is going in. That must sound all too familiar for Arsenal fans as those were the reasons behind Robin van Persie's move to United back in 2012.
The Dutchman finished as the top scorer during the 2011/12 season, but decided to force through a move to United at the end of the campaign due to being left unsatisfied by Arsenal's position. But ten years on, it's United that are on the receiving end of that problem.
United have let 11 first team stars go this summer, with Andreas Pereira soon to make it 12 as he moves to Fulham. But so far the only business they have done is for left-back Tyrell Malacia.
Elsewhere in the league, all other clubs have strengthened, with Liverpool and Manchester City showing their strength with an abundance of shrewd business. United are trailing behind, although that's been a common trait over the past few years in all avenues.
To further highlight their downfall, Ronaldo could complete a switch to Premier League rivals Chelsea. Not only would this be a major blow, it would leave United feeling the same sense of embarrassment and shame that Arsenal felt ten years ago.
The situation has flipped on its head, and United are starting to lose their status as the biggest club in England, that is if it hasn't already been taken away. Arsenal suffered for years as their stars secured moves to Chelsea, United and City, but it hasn't been a common issue for United.
But this would be the biggest one of them all. United's hero, their club legend, one of the best to ever play the game. Should he exit Ten Hag's project and move down to London, it will really hurt the club.
There were claims that Ronaldo was brought in for commercial reasons as well as obviously being a magnificent striker. But the ramifications of him leaving and seeing Chelsea as a step up could actually harm the club more than it initially did them good.
And with United yet to make more signings in the transfer window, what message is that going to send to all players considering a move? It's not a good look, but it's a reality that people have been avoiding at United for some time.