I doubt that this will get reversed by the entire D.C. Circuit sitting en banc, though such a reversal is not impossible; the D.C. Circuit is relatively conservative, and conservative judges have historically had different views on this question, as they have recently had on free speech, jury trial, and other constitutional rights. (Recall that Chief Justice Burger, who was indeed quite conservative, expressly took the collective rights view in public statements, though that was before the recent spate of scholarship on the Second Amendment, and before the modest turn towards libertarianism — at least as to enumerated rights — of modern conservatism.)
And if the D.C. Circuit decision survives a call for rehearing en banc, it seems to me that the Supreme Court will indeed agree to hear the case: There would be a square split between the D.C. and Fifth Circuits on the individual right side and several other circuits on the collective right side, a decision based on the individual right in favor of the challenger (so that the District can sensibly appeal), and what looks at first glance to me like a clean procedural posture (summary judgment for a plaintiff).
UPDATE: Several colleagues of mine at Mayer, Brown, Rowe & Maw, at which I'm a part-part-part-time academic affiliate, are representing the Violence Policy Center as amicus in support of the D.C. gun ban; I have been entirely uninvolved in the case, but I thought I would notice my colleagues' participation.
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