It's a great point.
Caitlyn Jenner struggled for many years to live her truth publicly—that she was a woman trapped inside a man's body—because of the backlash she anticipated she would receive if she were to live as a transgender woman. It was certainly very courageous of her to come forward to reveal her true self to the world, but that she was able to masquerade her gender identity in the first place is a privilege unto itself.
Meanwhile, Arthur Ashe—one of the first African-American tennis players to dominate the predominantly white sport—didn't have the luxury of hiding behind his skin color. Ashe experienced a lot of racism as he climbed the tennis ranks in the 1960s, a time when much of the nation was still in the throes of Jim Crow.
Hughley has a beef with how the ESPYs gave Jenner the Arthur Ashe Courage Award at this year's ceremony. He told a TMZ cameraman that he didn't think their struggles are comparable.
"[Ashe] was a symbol of courage. He fought [the] segregated South [and in] a very segregated profession," Hughley said. "He fought AIDS with dignity and honor, and Caitlyn Jenner put on a dress. I don't think it's the same thing."
Hughley went on to suggest that he thinks Lauren Hill, a college basketball player who died from brain cancer, should have received the courage award.
If it were up to Hughley, Jenner would not have been up on that stage this year.
"I don't know that [Jenner] would have been my choice, but obviously I'm not on the ESPY [committee]. I think Arthur Ashe and Caitlyn Jenner have very little in common."
Hughley also encouraged folks to stop and look at the treatment that Jenner has gotten in the media in comparison with Serena Williams, who has been taking a beating on the Internet by those who criticize her "masculine" frame.
"In the last month, we had the media telling us that Caitlyn Jenner was beautiful and Serena Williams looks like a man. That was a little weird to me. The man looks like a woman, but the woman looks like a man? I think that's ridiculous," Hughley said.
"I think Serena's one of the most beautiful things I've ever seen on a tennis court, and Bruce Jenner looks like every P.E. teacher I've ever had," Hughley said, smiling.
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Diana Ozemebhoya Eromosele is a staff writer at The Root and the founder and executive producer of Lectures to Beats, a Web series that features video interviews with scarily insightful people. Follow Lectures to Beats on Facebook and Twitter.