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I have to believe this is going to have to come to a head at some point
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For me, it is a wait-and-see on who Trump manages to get appointed to the Supreme Court. It will not be a cakewalk and Democrat's can still block his nominees by their 48 members supporting a filibuster (and again, a pox on the Republican's if they change the rules to allow a simple majority vote - it will bite them in the ass someday just like Harry Reid's "Nuclear Option" has done for the Democrat's with Trump's current slate of appointments).
However, assuming a strong pro-2nd Amendment candidate gets in, the next issue will be to get an MSR ban in front of the court and a subsequent favorable ruling. When that happens, New York will not be able to maintain its ban. At that point I suspect they would adopt licensing and registration, which has been upheld as constitutional. At this moment, according to the NRA, there are two potential cases heading to the Supreme Court:
1) Peruta v. California which seeks recognition of the fundamental individual right of law-abiding gun owners to carry a firearm for self-protection.
2) Binderup v. Lynch which seeks to overturn a recent decision by the U.S. Court of Appeals for the Third Circuit, where a divided court held that the lifetime ban in federal law on felons possessing firearms cannot be applied to some nonviolent individuals who committed relatively minor crimes many years ago.
So at this moment there are no cases that deal with MSR's heading to SCOTUS. That could change depending upon the results of the 4th Circuit en banc hearing on Kolbe v. Hogan that seeks to overturn the previous three judge decision that said Maryland's AWB had to be decided under Strict Scrutiny. The en banc hearing was this past May and still no ruling. I suspect the 4th Circuit may be waiting to see what they will have to deal with at SCOTUS in order to keep themselves from embarrassment of being overturned. Of course I would expect Maryland to appeal if the en banc ruling upholds the Strict Scrutiny ruling.