Legal Question in Criminal Law in Massachusetts

It's always beneficial to have a lawyer. But the honest answer is you could probably get away without one. Shoplifting is a misdemeanor that is punishable, as a first offense, by a fine of up to $250.

Your main concern is avoiding a conviction. While the penalties are different, a conviction on a shoplifting is a misdemeanor conviction the same as if you had been convicted for OUI, assault and battery, etc...

DAs are often willing to dismiss shoplifting charges in exchange for court costs, community service, or some other alternative disposition. See if you can get the DA to dismiss your case in exchange for one of those options. If not you might want to consider hiring a lawyer to help you avoid a conviction (I.e. don't plead guilty just to get the case over with...it will stick on your record for the rest of your life).