It can happen. Just ask Jonny Ramirez, who was an on-air radio personality and station manager; he also brought in sponsors for the station. The Tax Court said he was an employee for his on-air and managerial work, but an independent contractor for his marketing activities because the station didn’t control these activities. This classification is important because expenses related to his marketing activities were fully deductible on Schedule C, rather than being limited to itemized deductions on Schedule A (with the 2%-of-AGI floor).
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