Arsenal legend Alan Smith has painted a grim picture on the club's push to get captain Pierre-Emerick Aubameyang to put pen to paper on a new deal.
The Gabon international has entered the final 12 months of his contract at the Emirates Stadium and plenty of speculation has orientated around his future.
Arsenal want to keep the 30-year-old at the club but Smith doesn't rate their chances highly, suggesting that he might not have the patience to wait to secure Champions League football at the club.
"It all depends on results on the pitch. Top players want to be at Champions League clubs with the chance of winning that trophy. At the moment, Arsenal are not in that category," he told Sky Sports' The Football Show.
"This is where Mikel Arteta has a huge job on his hands to change that but to do that, you need money and quite a bit of it, more than Arsenal have got.
"What he is though is a manager of authority, he's won that group of players over, maybe he had a part to play on Arsenal being the only club to agree a wage deferral, which is an amazing feat and I think Arteta had a part to play in that.
"He's a good coach, they do listen to him, they do respect him. He will improve those players but he needs more and Aubameyang will be looking at the situation, at his age especially, and thinking 'have I got the time and patience to hang about here?'
"If they do lose him, it is a huge loss because he is a player who is almost guaranteed to get 25 goals a year at least. It's a tricky one for the club.
"I do think they're more organised now at the top, allowing players to run their contracts down, I think with Raul Sanllehi and Edu, they've got their act together a little more in terms of planning ahead. But have they got the cash and have they got the kudos now to attract?"