Shoplifting, Larceny, Robbery, Theft What are the chances of jail for my boyfriend

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My boyfriend stole some DVD's from a store, under $50s worth. He didn't go to trial instead they just game in probation. He did the community service but he only just got a job and we're barely able to eat with the money we get. He was doing his theft prevention class when my computer crashed and only yesterday got another one here. Today he got the paper saying when his court date is and it's August 31st. It said in the letter that conviction could possibly result in a capias arrest. I wanna know if he should just pled guilty and take the charges. and also what are the chances of him spending time in jail. And should we have his boss or anybody write a letter in his behalf to confirm the money problems? please let me know.
 
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