Legal Question in Business Law in Pennsylvania

If people who see your ad will realize he's the Monopoly man, then no. The character and his likeness are someone else's intellectual property. You can only use his likeness with the owners' permission. Even if they are willing to give you that permission (unlikely), you would have to pay for it.

You have two issues. One is copyright, so the creative expression is still protected unless the image was first published prior to 1926, And the other is trademark, so if your use presents a false association or is likely to confuse the market as to its source then this can be a problem.

If you need clarification, feel free to contact me anytime that is convenient.

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Frank

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That's about the worst idea I've seen posted here. Figure out something else for your billboard.

Good luck.