Taylor Silverman claims she and other female competitors were disadvantaged by officials at the Red Bull Cornerstone Contest, where she placed second and received a $2,750 award.
Trans skateboarder Lillian Gallagher was awarded $5,000 for placing first and winning two separate divisions - money that Silverman says she should have gotten.
Silverman, who has been skateboarding for 11 years, said when she tried to reach out to officials to "do the right thing even if it's not the popular thing," she was ignored.
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"I deserved to place first, be acknowledged for my win, and get paid. I reached out to Red Bull and was ignored. I am sick of being bullied into silence," Silverman wrote in an Instagram post, in which she tagged right-wing firebrands, Ben Shapiro and Candace Owens.
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The post has brought a slew of reactions, many of them supportive.
Other users have asked Silverman to have more compassion towards transgender women or get better at skateboarding.
Silverman's claims come at a time of intensified national debate about whether transgender individuals should participate in the traditional women and men categories in sports.
The most famous trans athlete - UPenn swimmer Lia Thomas - has broken multiple records, with critics saying she has a clear biological advantage not afforded to her competitors who were born female.
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"My name is Taylor Silverman. I am a female athlete. I have been skateboarding for eleven years and competing for several years," Silverman wrote in the controversial post, which has garnered more than 14,000 likes and hundreds of comments.
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She continued: "I have been in three different contests with trans women, two of which I placed second."
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"At the last contest series I did for Red Bull, I placed second. The trans competitor who won took $1,000 in qualifiers, $2,000 in finals, and $1,000 in best trick.
"This totaled to $5,000 of the prize money meant for the female athletes." Silverman went on to add that she took a total of $2,750, and "whoever would have placed third" lost the award due to Gallagher's participation in the contest
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Many people supported Silverman's decision to speak out about her experience at the competition.
Instagram user Corie Kenyon wrote: "Good for you for speaking up Taylor! I support you. Please try to keep in mind that the internet is not an accurate snapshot of reality so the abuse you're getting here is not the voice of those around you.
"The VAST majority of people even in the most liberal areas agree with what you're saying here. I am sorry you're getting abused for saying so."
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