Quite how the Gunners have allowed a situation like this to develop once again, over one of their brightest prospects, will infuriate fans who are already coming to terms with captain Robin van Persie wanting out.
What Walcott wants to do is unclear, he is yet to declare his intentions in the same way as the Dutch striker with who he linked up so well with last season, any many observers believe he is waiting to see what happens with Van Persie before making his own mind up.
Van Persie's role as captain, and a senior player mean Arsenal would approach negotiations slightly differently to Walcott, who is still to fully prove himself.
He had a hot and cold season last year, with some sublime moments, and is still on the cusp of truly establishing himself and taking his career to the next level.
Fans would resent it if he were to join Chelsea in the same way as Ashley Cole, and go onto win several trophies, he is still to win a single one with the Gunners.
Liverpool are hovering too, with talk that Brendan Rodgers sees him as a player who can help improve the side and inject some much needed pace to the attack.
The dilemma for Arsenal? Take the money and move on, or teach Walcott a lesson.
If Arsenal receive a bid of £15 million it will present a sizeable offer for a player with just one year remaining on his contract - but conversely given Walcott's potential, and the fact at 23 the best years are those immediately ahead of him, the Gunners will believe they are more than entitled to a fee in that region, given the years they have invested in the player's development.
Losing Walcott would be a hammer blow to Arsenal in what it would represent, rather than the loss of the player itself. It would underline Arsenal again as (a) a selling club and (b) a training school for young talented players before they reach their peak.
Sooner or later the Gunners have to prove they are no walkovers in the transfer market, and have to take a stand. They have already said they will not sell Van Persie, but given the need to resolve the future of such an integral member of their side, and the parallels with similar pledges and the disruption of last season with Nasri and Fabregas, few are confident Arsenal will make him see out the remainder of his contract.
Theo Walcott is just developing as a player, and has been keen not to alienate Arsenal fans in the same way Van Persie has, but you have to ask whether the contract limbo will continue and how long for.
Should Arsenal elect to keep him despite it, and not sell him, they will have two further choices- To keep him and play him, and hope they can persuade him to stay, or the toxic option of letting him rot in the reserves.
It is doubtful the latter is Wenger's style, Arsenal have rarely done this, and last season when Nasri was desperate to quit he was still selected to start in a home loss to Liverpool in August - although this was brought on by an injury and selection crisis.
Even so, the Gunners need to show a ruthless streak with their players sooner or later and show they will not be walked over. If they do not, Walcott and Van Persie will not be the last players to get to this position, more could seek to follow them out the door.
What should Arsenal do with Walcott if he does not sign a new contract?
What should Arsenal do with Walcott?
image: © Ronnie Macdonald