It is conceivable that he could. Dv strangulation is a felony with a 5 year maximum sentence. It will depend on a lot of factors. If she took your car without permission, call the police.
Yes, your son can go to prison.
Recovering your property is more complicated. Your son, no doubt, has a no contact / stay away order - and this includes direct or indirect by himself or through a 3rd party, which would include you. I suggest that you call the local police department and see if they will accompany you to her residence to recover your property.
Unfortunately, while this will protect both you and your son from being accused of unlawful contact (the presence of law enforcement precludes the possibility that you or he contacted her in violation of the stay away order) it will not guarantee the return of your property (i.e. she is free to deny that she has any of your property). If she is up front and honest then the police should "assist" you in collecting your property, if not then you will be left with no recourse except to seek a Court Order.
A civil suit (small claims or otherwise) is one way to go about it, but you can also petition the criminal court judge for an Order directing that the victim return your property. I would suggest trying to recover the property with police assistance first and if that fails then ask your son's criminal attorney (whether private or court appointed) to speak to the prosecutor, and if that doesn't work out then to file an appropriate motion.
Either way DO NOT CONTACT the victim (even an innocent contact by you for your own purposes unrelated to your son COULD be enough to violate his no contact / stay away order) and good luck!
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Domestic violence by strangulation is a third degree felony in Florida, meaning he could theoretically get 5 years in prison, though it would be unusual for a first-time offender to get prison time. If the ex-girlfriend refuses to give you your stuff, your only legal option is to go to court to sue her for the value of your stuff. If you aren't willing to or can't pay to do that, then you don't have any court-based options. The police will probably just tell you to go to court.
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Whether or not someone will goto prison is a commonly asked question--especially when someone's loved one is arrested for a crime. The answer depends on the charge listed on the information. If the prosecutor's office charges the crime as a felony then the possibility of going to prison increases, however, other factors such as a person's prior record, victim's injury etc. play a tremendous role in the decision making process. A person charged with such a charge can be exposed to a sentence of prison, jail and/or probation. One should always consult an attorney in such serious matters, because an allegation of a crime does not mean that the person is guilty of such a crime. A competent defense attorney can challenge the allegations set forth by the prosecutor and reach out to the prosecuting attorney for a plea or nolle prose.