Okay, here’s a suggestion. Problem is, it’s not tongue in cheek, and technically it’s not losing money, more like giving it away. If you’re all about street games, take the money to the streets! Start with New York since that seems to be where many of our roots are. Have a city-wide street games tournament and exhibition – give prizes and award money! Get sponsors – that way they can lose their money too! Maybe make it an annual thing. Imagine streets of the City closed off to punchball games, stickball games, skelly (or skully depending on where you were from), jacks, jump rope, etc.
If it loses enough money in New York, you can take the show on the road and lose money in other urban areas.