My Husband Wants to Leave His Business to My Entitled Stepsons. I Have to Change His Mind.

Pay Dirt is Slate’s money advice column. Have a question? Send it to Kristin and Ilyce here. (It’s anonymous!)

Dear Pay Dirt,

My first marriage left me a wealthy widow where we had several vacation homes but sadly no children. My second husband has two adult sons and a thriving business that is basically his third child. Despite us both being retired, he is still very involved in the business. Neither of his sons ever showed interest in taking over, so my husband has been approaching his lifelong employee, “Mike,” to take over. Mike has been working for my husband since he was 17 and is a nephew in all but name. But now my husband is talking about selling the business and giving shares to his sons.

My husband has been very generous to his sons: He paid for college, new cars, and large gifts for down payments. Even before he met me, he was clear that he expected his sons to stand on their own two feet and make something of themselves.

Everything was fine until “Kim” showed up. She is the second wife of my oldest stepson. They had an affair and it was a messy divorce—thankfully no children were involved. Kim has zero shame and zero sense of anything but naked entitlement. The divorce wasn’t even final when she started to badger us about paying for her dream wedding. We declined and told my stepson if he was old enough to run his life this way, he could find a way to pay for it.

And it has been downhill since. Kim has expensive tastes and my stepson went from living within his means to being tens of thousands of dollars in debt. Kim has poisoned her husband against mine about how “Dad owed them.” We tried to offer help, paying for a financial planner and bankruptcy lawyer. There was never a desire to be better, just demands for money.

This attitude affected my second stepson and his wife. We took them on vacation to our beach house and my daughter-in law-made many comments about how she would decorate “when” she gets the house rather than “if.” Later, she made the demand for the use of another property for some random relative. I told it that was impossible since it was leased out and she told me to cancel and kick out my tenant. I told her where she could stuff it and to consider any access to my properties revoked.

Now our relationship with both his sons is very strained. Any olive branches get torched by more demands for money. It is getting to my husband. He is increasingly talking about selling the business he spent his life building up and giving shares to his sons while leaving as Mike the general manager. I told my husband that his sons would sell off the business for a quick buck, blindside all the employees, and it would be a betrayal of Mike. He would lose everything and gain nothing because his sons knew nothing but greed now.

Mike has been nothing but good and loyal. He and his wife are talking about buying a house now and staying rather than taking up any other offers Mike has gotten. He turned them down out of loyalty to my husband. Mike has no clue what my husband is thinking about. I usually stay out of these matters but Mike is the son my husband should have and not these vultures. I don’t want to see him hurt and left in the lurch. What should I do?

—On Mike’s Side

Dear Mike’s Side,

Wow, your stepsons seem like a piece of work—what a stressful situation. Are you suggesting that your husband leave the business to Mike? If so, why not have a direct conversation with him about it? He seems attached to Mike, after all, and your stepsons don’t seem terribly interested in the business anyway.  It seems like it would be in everybody’s best interest to hand the proverbial keys over to Mike. And if he’s pretty much family already, is it really that big of a stretch?

There are gentle ways to bring up this idea to your husband without throwing shade at your stepsons, even if they deserve it. You can assure him that his boys would still be taken care of in this situation. There’s no need to harp on their entitlement and nasty behavior, but you can bring up the fact that they have a hard time managing money to begin with, so giving them shares of the business might not be financially prudent. If it helps, ask if you can talk to your financial planner about it, because it might help your husband to hear the suggestion from a neutral third party.

Your stepkids’ behavior is also unacceptable, though. They’re making plans for inheriting your beach house right in front of you? That must be incredibly hurtful. This is a separate conversation, but at some point, your husband needs to set some ground rules with them. It sounds like he’s tried and it hasn’t gone over well, in which case, it might be time to stop extending those olive branches—it sounds like it’s costing you.

—Kristin

More Money Advice From Slate

My late husband was quite wealthy, but he passed away unexpectedly shortly after retiring. He left a small-ish (but enough to pay for Ivy League college and grad school) portion of his money in a trust to his then-teenage son. He left the rest of his money, shares in his company, and other assets to me. I have always felt guilty about getting so much when my stepson should have gotten more, so I have always helped him out—putting more money in accounts for him and his family, buying him his first apartment and house, paying for his wedding. This meant my stepson has lived a luxurious lifestyle while working at a job he enjoys and earning a low salary. Now he’s done something I cannot forgive.