None can predict. He may be facing jail. Needs attorney ASAP.
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It depends on what you mean by work out. I suggest you retain a good criminal defense lawyer.
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Yes, although your son's background in similar conduct in the past will make things more difficult in dealing with the prosecutor.
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The fact that your son was arrested, released at arraignment and already scheduled to appear in Supreme Court on the indictment, suggests that he is being given special treatment by the Kings DA. He needs a good criminal attorney and needs one quickly. The prognosis if he waits is bleak. You must choose between spending your money on a lawyer, or on the rest of your family. If you are committed to saving him, you may contact me at email@example.com. There are no guarantees.
He is not being given any special treatment at all. That is a incorrect statement. My guess is that he is scheduled to appear in Supreme Court in Part AP1 in September? The long date is because he was released by the Judge at arraignments, and is totally typical for an "out" or released defendant. In the interim time period, the DA's office is deciding whether or not to indict him. They will most certainly take his past behavior into account. This is a good time to hire an attorney, so that you can get any and all information from the DA's office. This window between now and the next court date, is the prime opportunity to work out a plea.