Arsene Wenger's stock as Arsenal boss has seemingly plummeted to an all time low, but his reputation will be damaged even further if he is unable to retain the services of Robin van Persie.
The end of this season will herald the seventh in succession that the Gunners have gone without any silverware, but the failure to finish in the top four will do even greater damage to their ambitions.
A lack of Champions League football is likely to have some bearing on Van Persie's decision over his future, with the Dutchman's current contract set to expire at the end of next season.
Van Persie has yet to give any clear indication that he will extend his stay at the Emirates Stadium, and has put any contract discussions on hold until the end of the season.
However, if the 28-year-old decides he would rather leave north London for pastures new then, claims Goal.com, Arsenal will not cash-in like they did with Cesc Fabregas and Samir Nasri, but rather force Van Persie to run down his contract.
This is reported to have left Van Persie feeling 'powerless and anxious' as he considers his future, while a number of clubs are likely to sound him out in the summer.
The losses of Fabregas and, to a lesser extent, Nasri last summer were significant blows to Arsenal, but the departure of Van Persie could prove to be the most significant during Wenger's 16-year tenure.
When Fabregas left for Barcelona, the Gunners were losing their captain and a player with supreme talent and potential.
However, after the loss of one of his leaders, Wenger was able to promote Van Persie to skipper and task the Holland international with commanding the Arsenal dressing room.
Van Persie has certainly relished his new role and, after an injury free season, as established himself as one of the finest players ever to wear the famous red jersey.
However, although the departure of one icon and leader is hard to take, it can be dealt with. The loss of a second in quick succession could be catastrophic for Arsenal.
Van Persie is Arsenal's figurehead and talisman, their leader and most influential player. If he leaves, then what is left of Arsenal?
Wenger does not need anyone to tell him the importance of Van Persie to his side, but it really is imperative for the Gunners to retain his services.
Securing the signature of Van Persie could prove to be more important than any acquisition Wenger has made in his illustrious career. But losing Van Persie could prove to be his most disastrous mistake.