Final presidential debate moderator Chris Wallace faces the challenge of asking Republican presidential nominee Donald Trump about the numerous allegations that he sexually assaulted several women, but Wallace’s ability to confront Trump’s treatment of women is no doubt tainted by his own history of sexist and sexually charged rhetoric about women.

Wallace, anchor of Fox News Sunday, has made numerous sexually charged remarks about women, such as calling the National Transportation Safety Board chair a “babe” and remarking that “you would not expect a government bureaucrat to be an attractive woman” and making creepy comments about former Republican vice presidential candidate Sarah Palin for years. Appearing on conservative radio host Mike Gallagher’s show in 2009, Wallace asked if Gallagher could “put in a good word” for him with Palin. Just a few months later, on Imus in the Morning, Wallace replied, “one can only hope” when asked if Palin would be “sitting on [his] lap” during an interview. Even the hosts of Fox & Friends, who are no strangers to sexism, confronted him over those comments. Wallace also explained in 2011 that one of the reasons he was “dazzled” by Palin is that she’s “very attractive.”

In 2015, Wallace again stirred controversy when he remarked that singer Kelly Clarkson, who had already been fighting an onslaught of body shaming in the media, “could stay off the deep dish pizza.” The comment brings to mind Trump’s statements about former Miss Universe Alicia Machado, whom he called “Miss Piggy” and described as an “eating machine.” Wallace did eventually apologize, calling his comment “offensive.”

Making fun of Clarkson’s weight, however, was not the first time Wallace ridiculed a woman’s appearance. In 2013, Wallace approved of a New York Post cover photograph of a supposedly angry Hillary Clinton labeled “No Wonder Bill’s Afraid,” which was heavily criticized as “blatantly sexist” and “offensive sexist garbage.” Wallace called the cover “funny” and asserted that “nice can be overrated sometimes.” With a history of comments like this, how will Wallace approach Trump’s dismissal of People reporter Natasha Stoynoff as too ugly for him to assault?

Wallace’s history of making sexist comments taint his ability to confront Trump over the vulgar video of the candidate boasting about sexually assaulting women and the increasing number of women accusing him of inappropriate sexual conduct. Although Trump denied that he had sexually assaulted women, the mounting accusations allege that his words were in line with the sexually predatory behavior he bragged about in the 2005 tapes.

Wallace’s role as debate moderator poses other challenges as well. Wallace changed his stance on fact-checking in debates (he says it’s not his role, even though he corrected Trump during a primary debate), and he has been wildly inconsistent in how he talks about immigration. Additionally, a Fox News host is hardly the most appropriate moderator for this debate given that Trump has retreated to the station as a safe space -- and avoided other press -- while his campaign implodes under the allegations of sexual harassment and assault.