This rule breaks the game. Two players make an agreement: one player will repeatedly give all their money to the other and then declare bankruptcy. After repeating this cycle as many times as they like, they divide the money.

Potential objections:

• "Careers is a silly American board game, why are you still playing that?" It's not as good as modern games, but it's one of the more fun games from the era and has an aesthetic that's entertaining with the right group in the right mood.

• "Can you make this sort of agreement?" The game has a market, in the sense that you're allowed to buy and sell things. Typically in these games you can trade money for some future promise unless the rules forbid it, though there's nothing to compel the other person to follow through. You could decide not to allow this, though in most games this is a dynamic that's a lot of fun.

• "Won't the person accumulating the money just keep it all?" Not the people I typically play with. People care about maintaining a reputation as someone who keeps their word in games more than they want to win a single game.

• "This isn't fun." I agree. Next time I play I want some sort of house rule that makes this not work. Not sure what rule yet though. Suggestions?