Money is no object. How do you (legally) ruin your worst enemy's life?

Hire thousands of actors talented enough to emulate his and his families mannerisms. Buy every house within a mile of his home, and redesign each house to match his. Fill the houses with the actor families.

Buyout whatever business he's involved in and replace everybody with his doppelgängers. Continue this process with every aspect of his life until he is surrounded with completely like-minded and physically similar clones.

He will slowly become more and more unnerved, working and living around people so similar in thought that he may as well be alone. As he continues to live in comparative obscurity, his world will gradually darken to shades of grey. Nothing in life will captivate or excite him.

As he struggles to escape from the confines of basic-bitch'dom, he will begin acting out, searching for a release. Unfortunately for him, you've bought out every enticing business in the city. Every strip club, laser tag room, bowling alley, bar, etc is bought out and turned into a Starbucks or a Jimmy Buffets. Sure he can spring the cash for a trip to vegas once a year, but in the back of his mind he knows he will be returning to a life of mediocrity.

Once he reaches his lowest point, you build a house next to his. A beautiful mansion with every manly wetdream possible. Ask him over for dinner, apologize for past transgressions, and smoke a cigar with the man. Become his best friend, and provide the only form of escapism from the rest of his monotonous existence.

Then one Sunday invite him over to watch a game. When he comes to the door, greet him by the wrong name and drag him inside before he can respond. Inside will be all of his closest backup "friends" and coworkers. You pick one lookalike from the crowd, introduce him to your enemy as your enemy, then casually walk off.

Then move away and never talk to him again. Continue to hire the actors for the rest of his life.

/r/AskReddit Thread