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Brian, a US citizen and a resident of California, signed a contract with an Italian clothing company to promote their winter and spring clothing lines.

Brian, a US citizen and a resident of California, signed a contract with an Italian clothing company to promote their winter and spring clothing lines. A photographer, engaged by the Italian clothing company, will take photos of Brian modeling the outerwear for the clothing company for use in their advertising campaign (e.g., print and social media). One set of photos will be taken in Milan, Italy in December 2022 and another set of photos will be taken in Los Angeles in February 2023. Brian will be paid $125,000 for each photo shoot. Brian has asked you about the income tax consequences of the payments. He concerned because the Italian clothing company has indicated that they may have to withhold some Italian tax on the payments but he heard there may be a way to avoid it. Determine the US and Italian tax consequences of the two payments, if there is any opportunity to avoid withholding on the Milan payment and what steps, if any, Brian should take now obtain the required documentation.

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