The Moneyist: My ex-husband borrowed money to pay for his wedding to a woman 40 years his junior — how do I protect my son’s $1M estate?

Dear Moneyist,

Last year, my husband and I divorced after nearly 25 years of marriage. We had been separated for many years prior to the divorce. We have a very nice 22-year-old son who is a senior in college. We all live in New York, although my son might move elsewhere after college.

My ex-husband has always been terrible with money. He wasn’t able to pay his half of our son’s college tuition and decided to take out parental student loans. One year, he borrowed from his retirement account. He owes the Internal Revenue Service $150,000 in back taxes. He can’t afford to contribute to my son’s living expenses, so I pay for everything.

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A few months ago, my ex-husband, 70, married a woman 40 years his junior and had to borrow money from family members to pay his portion of the wedding and buy her a wedding ring. Even though he’s deeply in debt and can barely pay his rent, he’s discussing the possibility of having additional children with his new bride. She’s a student in law school and my ex-husband is a lawyer/college professor.

So here’s my problem. I want my son to inherit my entire estate, which is valued at about $1 million. But my biggest fear is that, if I die before my ex-husband, he will find a way to take my son’s inheritance. My son is very mild mannered and has never been able to stand up to his father, who is domineering and arrogant.

If my ex-husband asks our son for money to help with his new family and future children, my son would be afraid to say “no.” How can I structure a will so that my ex-husband can’t get his hands on my son’s inheritance?

Ex-Wife, Concerned Mother

Dear Ex-Wife,

As we say in the journalism business, you buried the lead.

This charming fellow is not your problem anymore. He is somebody else’s affair. He can work his academic charm to get what he wants from his new wife, family or friends, but it won’t work on you anymore. He may or may not have more success there. This was a red wedding to end all red weddings: Borrowing money to pay for his wedding, owing the IRS $150,000 in back taxes, struggling to pay his rent and all the rest of this puffery and nonsense are all red flags. You are home free and, with a little help from an estate-planner, so is your son. You are doing the right thing: Planning ahead and anticipating your ex-husband’s behavior based on his past actions.

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You can put money into a trust fund for your son’s education, his children’s education and/or his housing. You could put your own home into an irrevocable trust for your son and his future family. Incentive trusts that reward good behavior are controversial, but I’m here to tell you they exist. Here are some tips for how to proceed: Choose the right executor to carry out the wishes stated in your will, include personal property of both sentimental and monetary value.

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Talk to your son. Transparency will help allay any posthumous resentment. Tell him your plans and seek his feedback as well as the counsel of a good estate lawyer. It may also help your son’s self-confidence to know that you are including him in the estate-planning process and it will help him to realize how important this is. Look into what you can do for your son while you are still here. How can you help him stand up to — not only his father — but other domineering figures in his life, including his boss or even a future partner? None of this will matter a jot unless he learns to advocate for himself and make good choices.

I apologize in advance for giving you another issue to worry about.

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Do you have questions about inheritance, tipping, weddings, family feuds, friends or any tricky issues relating to manners and money? Send them to MarketWatch’s Moneyist and please include the state where you live (no full names will be used).

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