Despite Wenger saying in late August that he had a verbal agreement with the winger, and the 23-year-old telling ITV he wanted to remain at the club, he did add a condition to it. He wants to play as a striker.
These next two months are going to be crucial in his decision to stay or not, because he will hope for chances up front.
If he can't get them now, then what chance come January when the transfer window re-opens, and Arsenal have a chance to spend their rumoured £35 million transfer-kitty.
One of the clubs he has been persistently linked to is Chelsea, who according to reports over the weekend are set to re-kindle their interest in him.
Walcott's contract situation means that as of January he will be free to negotiate with clubs and sign a pre-contract agreement for a summer switch.
But would he actually be better off if he moved to Stamford Bridge?
The answer is probably not.
Roberto di Matteo is building a side with one of the most fluid, interchangeable attacks in football. The talented Hazard, Mata, Oscar, Marin and Moses can all play across the frontline, in support of Fernando Torres.
Walcott may feel as though he wants to play in such company, and even better, to play as a striker with them in support. They would certainly give him the chances he would need to prosper.
But would he actually be used as a striker? It is hard to predict the mind of Di Matteo, who may have him earmarked for such a role, but it appears Chelsea have other more proven striking targets.
As well as Torres and Sturridge in attack, Chelsea are expected to spend big this January, with Radamel Falcao, Loic Remy, and Fernando Llorente all possibilities.
If Walcott was to see this in January, he may wisely decide his chances up front will be even more limited than at Arsenal.
Perhaps Liverpool and their striking crisis would open up better for him to fulfill such a role, but as most Gooners would revel in telling the winger, the Reds are a step down at present from Champions League regulars Arsenal.
Our conclusion is that Walcott should stay where he is, he may just not be cut out to be a striker. Arsene Wenger has famously converted wingers to play up front in the past, Thierry Henry anyone? And if he can't do it with Walcott then it might just not be meant to be.
Walcott should place his faith in the club and manager who did the same to him as a 16-year-old, rather than make a very unpopular move across London to Chelsea and risk spending more time on the bench than on the pitch.
Where do you think Walcott's future lies? Chelsea or Arsenal? Up front or on the wing?
image: © Ronnie Macdonald