Well, good thing he’s one of the top 10 winningest Supreme Court litigators extant, nicht wahr?
Winning in court doesn't win the election. The Damage can be done in the court of public opinion and the Legal court rulings won't save him in the election.
Beyond that, he might actually face a very serious challenge in court. As Nero Germanicus almost had a meltdown when I pointed this out, perhaps you should consider it as well. I noticed that Ray76 has already mentioned it, but I don't think he highlighted the salient point.
“A person born out of the jurisdiction of the United States can only become a citizen by being naturalized...”– U.S. v. Wong Kim Ark-
I believe "Wong Kim Ark" has been bandied about for the last seven years as the most salient defining court decision on the topic. If Wong Kim Ark says you *MUST* be born inside the Jurisdiction of the United States then that's a pretty tough opinion to ignore, especially after so many people have said "Wong Kim Ark" was the last word on the subject.
And that doesn't even address the problem of arguing away the "Rogers v Bellei" decision.