What are your chances of prevailing in court? There is absolutely no way to tell you that and anyone who says they can on a message board is full of "it." You need to hire an attorney to determine what evidence, if any, you have that undue influence was exerted. These types of cases are very hard to prove as you would need eyewitnesses and perhaps medical records. Start now if you are serious by having an attorney investigate the case with you.
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Did your brother die? If NO, any challenge would be premature. If YES, I suggest you consult a trusts and estates lawyer.
I am a former federal and State prosecutor and now handle criminal defense and personal injury/civil rights cases. Feel free to check out my web site and contact me at (212) 577-9797 or via email at Eric@RothsteinLawNY.com. I was named to the Super Lawyers list as one of the top attorneys in New York for 2012. No more than 5 percent of the lawyers in the state are selected by Super Lawyers. The above answer is for informational purposes only and not meant as legal advice.
Wait until he passes and then see what the will says. You can retain an estate lawyer at that time to fight the will. Percentages are unknown and premature. Good luck.
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I have the same concern as my colleagues -- is your brother still alive? Perhaps the woman to whom your brother apparently wishes to give his assets is "not a girlfriend in the traditional sense," but it seems to me that that is not really your concern. Besides, I'm not sure what a "girlfriend in the traditional sense" is. Maybe worrying about what your brother's will says while he is still alive might make you "not a brother in the traditional sense."
But none of that is your actual question. Your real question is what is the precise percentage of your successfully challenging your brother's will. The answer is 41.2569%.
Am I serious? No, of course not. But there is a percentage I can provide you with: If your brother is alive (as I think your posting suggests) and he learns of your posting, I think I can predict with virtually 100% accuracy that he will be beside himself with anger at you.
Good luck to you. And to your brother.
Michael S. Haber is a New York attorney. As such, his responses to posted inquiries, such as the one above, are limited to his understanding of law in the jurisdiction in which he practices and not to any other jurisdiction. In addition, no response to any posted inquiry should be deemed to constitute legal advice, nor to constitute the existence of an attorney/client or other contractual or fiduciary relationship, inasmuch as rendering legal advice involves the ability of the attorney to ask appropriate questions of the person seeking such advice and to thus gather appropriate information. In addition, an attorney/client relationship is formed only by specific agreement. The purpose of this answer is to provide the questioner with general information, not to outline specific legal rights and remedies.