Chris Penner was ordered to pay $400,000 to a group of transgender men, whom he banned from his Portland, Oregon bar, the "P Club," last year.
The judgement was issued by the Oregon Bureau of Labor and Industries, which interviewed 11 transgender members of the "Rose City T-Girls."
Penner allegedly told the leader of the group, "Cassandra Lynn," how his bar was losing money because of them and told the men not to come by anymore, noted OregonLive.com.
However, the bureau found no evidence that the transgender customers disrupted business.
Lynn (pictured) told a judge about not being able to sleep for the months after getting Penner's message. The T-Girls stopped going out in public as women.
The $400,000 order is the first imposed under the 2007 Oregon Equality Act, which protects the rights of LGBT people. Penner must also pay another $5000 fine to the state.