As law school has given us the power to say with great authority, it depends. Is this a civil ordinance violation or a criminal charge? You never go to jail on a civil ordinance violation. It is just a fine.
If it is a criminal charge, then you are facing jail time. The amount of jail time depends on the value of the item(s) involved. Whether you actually receive jail time depends on a number of factors (i.e., you - your education, employment, community contributions, etc.; the facts of the case; the prosecutor; the judge; etc.). Your repeated history of retail theft will be an aggravating facotr. But even knowing all those factors, the best an attorney may do is offer you an educated guess. DO NOT post any of these factors online. Anything posted online may be used against you in court.
If this is a criminal offense, you need an attorney on your side. Contact local, experienced criminal defense attorneys for more specific advice. If you cannot afford a private attorney, contact the local public defender's office. If you do not qualify for public defender assistance, then ask the court to appoint a low cost attorney to your case.
You have been given very sound advice by attorney Missimer. If this is a criminal charge I think you should if at all possible retain a local private criminal attorney.
This is not intended to be legal advise or as legal representation. I am a California personal injury attorney . Be aware that every state has its own statute of limitations; and statutes & case laws that govern the handling of these matters.
I certainly agree with Atty. Missimer's answer in all respects. I'll just point out that for subsequent retail theft criminal charges, I usually see prosecutors in Brown County offering a year of probation with a small amount of jail (10 to 60 days) as a condition of probation. The maximum for retail theft under $500 is a $10,000 fine, nine months in jail, or both. But, as she notes, it depends on a whole lot of things.
You absolutely need to get an attorney if this is a criminal charge. There's one judge who has a reputation of being tough of retail theft, and some of the prosecutors can be quite difficult to deal with. A local attorney will know what to do in those situations so that you get the best resolution possible.
Disclaimer: This is legal information; not legal advice, so don't rely on it. I'm a lawyer, but I'm not YOUR lawyer. If you need legal assistance, you should contact a lawyer licensed in your state.