George Conway Confronted on Post 'Shaming' Alina Habba for Her Looks

Conservative lawyer George Conway was confronted online on Saturday about a post he made in which he seemed to be "shaming" Donald Trump's lawyer Alina Habba on her appearance.

Habba has recently gained attention for representing Trump in his civil defamation trials brought against him by former Elle columnist E. Jean Carroll, who accused him of defaming her when he repeatedly claimed she was lying about allegations that he sexually assaulted her in a Manhattan department store changing room in the 1990s. Last year, a jury found him civilly liable for abusing Carroll and defaming her for comments he made in 2022, ordering him to pay $5 million in damages. On Friday, a jury ruled in another case based on comments he made in 2019, ordering the former president to pay $83.3 million in damages.

Conway, an outspoken Trump critic and the estranged husband of former Trump adviser Kellyanne Conway, took to X, formerly Twitter, on Saturday and wrote that he was considering taking aim at the use of "silicone," adding that it "doesn't make you smart."

"I was gonna tweet 'silicone doesn't make you smart' in response to something on here but I thought better of it and didn't do it and I'm not gonna say whom it was about," he wrote.

Newsweek has reached out to Conway via Society for the Rule of Law's email for comment, in which he serves as board president.

Although Conway did not mention anyone by name, the comments on X seem to refer to resurfaced remarks made by Habba in a January 4 interview in which she said, "Somebody said to me 'Alina, would you rather be smart or pretty?' and I said, 'Oh easy, pretty...I can fake being smart.'"

Newsweek has reached out to Habba's office via email for comment.

The resurfaced remarks come after Habba has had several terse exchanges with Judge Lewis Kaplan, who oversaw Carroll's civil defamation cases. At one point during the second trial, Habba protested that she did not "like to be spoken to that way" after being told to "sit down" when a request to delay the trial over the funeral of Trump's mother-in-law was rejected.

Conway's X comment struck a cord with MSNBC legal analyst Lisa Rubin, who confronted Conway about his post and wrote on X, "Shaming women for their looks and/or aesthetic choices in this still deeply misogynistic world is no more cool when directed to women loyal to Donald Trump than it is when applied to E. Jean Carroll and her allies."

In her post, she also wrote that she disagrees with Conway's view of looks in respect to knowledge.

"You know that in many respects you and I agree on our legal analysis. But here's one place where we diverge silicone may not make anyone smarter, but it doesn't make anyone dumber or weaker either. That said, I am adding my two cents because I know you to be genuinely invested in women's autonomy and professional success, including mine. Fair?" Rubin asked.

In response, Conway apologized and wrote that although he did not name anyone, he does not seek to shame anyone for their looks or aesthetic choices.

"Fair, Lisa. I'm sorry if I offended you, or anyone else. In truth, I don't question the attractiveness of any person, including (and especially, I confess) the person who I could have been referring to, and don't seek to shame anyone for their looks or aesthetic choices (with the exception of people who have a penchant for wearing unnaturally orange makeup)," he wrote on X.

However, Conway seemed to reiterate to Habba's resurfaced remarks, writing "that person deserves a little grief for that."

"But if someone—again, not specifying who that might be—were to suggest that it's better for a woman to better pretty rather than smart, because a woman could fake being smart, I think that person deserves a little grief for that, even though I didn't specify whom that might be. Particularly if that person engaged in idiotic and exceedingly mendacious behavior before a court of law and the public at large. Speaking hypothetically of course. Again, I apologize if I've given offense. If I had named anyone in the tweet I would take it down. But since I didn't, I'll let it stand and I'll own the lumps," he added in his post.

Rubin wrote back to Conway: "Appreciated (even though no offense taken.) And fully agreed that smart beats pretty every day of the week. As I told one of my girls last week, pretty fades; smart & funny lasts. Xx."

This is not the first time Conway has criticized Habba. Earlier this month, he mocked her and the former president over Habba's cross-examination of Carroll in an X post.

During her cross-examination, Habba questioned Carroll about her association with famous figures known to be critical of Trump including his estranged niece, Mary Trump, comedian Kathy Griffin and George Conway.

"If you're wondering just how dumb Trump and Habba are, this may help," Conway wrote at the time, while sharing a transcript of Habba's exchange with Carroll.