Legal Question in Family Law in Massachusetts

Yes, the court can order him to pay alimony based on your ability to get a job or otherwise may be capable of generating income. If he and his wife operate a business he is employed. He may not be making any money, but the court could determine he is capable of earning $X per year and allow him time to catch-up but he could and probably will be required to pay alimony. They have done it to a former judge who wanted to retire and reduce his alimony and they told him he still had to pay the same alimony.

I suggest he goes and gets a job or opens a new business.

He should consider retaining an attorney to advise him on this fact specific situation.