Donald DeLong, an estate attorney based in Southfield, Mich., had a client with a $5 million estate who said that if any of his grandchildren went to Ohio State University-an archrival of the University of Michigan, the client's alma mater-they would be disinherited.

"This was a rabid University of Michigan graduate," DeLong says. "Everyone who went to U of M hates Ohio State. This client specifically had me write in, 'If anyone attends Ohio State, they get nothing.'"

DeLong says he had another client who so detested her mother and siblings-she had no spouse or children-she thought leaving them nothing would be too kind. So she left each of them checks for $9.99, because she thought that would hurt them more.

John J. Scroggin, an estate attorney in Roswell, Ga., had one client who said his daughter would not get her entire trust fund until she divorced her current husband, a man he referred to as a "dandy scallywag." The son-in-law was married two or three times before, he's never held a steady job, yet he drives a nice car and is a very sharp dresser. He's about a decade older than the man's daughter. The client's trust prohibits the daughter from receiving anything while she's married to the man. He instructed the trustee to keep the provision a secret and to never give copies of the trust documents to either the daughter or her husband, unless he is required to do so by a court order.

"He clearly did not like his son-in-law," Scroggin says. "He thinks the guy is a ne'er-do-well who will spend all of his money when he dies."

Scroggin says he had another client who put so many detailed provisions on his son's inheritance into his will, they were surely going to cause conflicts in the family after he was gone.

"He was absolutely against the idea of the child having any control whatsoever over this trust fund, and I was never quite sure why," Scroggin says. "It probably wasn't a very good relationship, and it wasn't likely to get any better after he was gone."

Some prefer to take the carrot and stick approach, offering to sweeten the pot for family members who carry out the benefactor's wishes. Carl Archer, an attorney with Maselli Warren in Hamilton, N.J., says he's seen people offer to give family members an extra $10,000 if they go to a particular college or if they marry or divorce a certain person.

"I haven't seen a lot of really crazy stuff, because people who come up with the really crazy stuff are crazy. You don't want someone coming in with delusions of grandeur," he says.

Instead of putting stipulations into their will or trust documents, some people are empowering their trustees with more discretion. It's become common for benefactors to give trustees the power to halt distributions if they suspect the money in the trust is being used to buy drugs or bet on horses, or being used for some other type of activity that the trust did not anticipate, says George Ragland, a senior attorney with Womble Carlyle Sandridge & Rice in Winston-Salem, N.C.