Robert Geary (plaintiff) was a police officer in San Francisco. In 1992, after the San Francisco Police Department (the Department) encouraged officers to engage in creative community policing, Geary started patrolling with a ventriloquist’s dummy called Officer Brendan O’Smarty. Geary used Officer O’Smarty to break down barriers between the police and the neighborhood he patrolled and gained national media coverage. The Department told Geary to get rid of Officer O’Smarty. The San Francisco Board of Supervisors interceded and passed a resolution asking the mayor to tell the Department to allow Geary to patrol with Officer O’Smarty. The mayor ignored the resolution. Geary then decided to appeal to voters, forming a committee and circulating a petition for a ballot initiative that would make it a city policy to allow Geary to patrol with Officer O’Smarty. Geary spent over $11,000 promoting the petition and deducted the amount on his income-tax return as business-related advertising expenses. The Commissioner of Internal Revenue (the Commissioner) (defendant) determined that Geary could not deduct the expenses related to his petition because they were lobbying expenses, and § 162(e)(2)(B) of the Internal Revenue Code disallowed deductions on any amount spent in connection with an attempt to influence the public. Geary argued that his goal with the ballot measure was to increase awareness of his community-policing efforts, not to influence the public. Geary petitioned the United States Tax Court for a redetermination, and the tax court, agreeing with the Commissioner, held that the expenses were not deductible because they were lobbying expenses designed to influence the public with respect to a legislative matter. Geary appealed.