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"I think he's a person I know well - he is a good person," Trump said in an interview with the New York Times.
"I think he shouldn't have settled. Personally I think he shouldn't have settled," he added. "Because you should have taken it all the way. I don't think Bill did anything wrong."
The defense came just days after a Times report this weekend detailed five sexual harassment suits that O'Reilly and Fox settled with former coworkers, who alleged repeated instances of verbal abuse, lewd comments, and unwanted advances.
On Tuesday, over 20 advertisers publicly pulled ads from "The O'Reilly Factor," while some groups have called for the host to resign.
"A man who bragged about committing sexual assault and grabbing women by the pussy is defending Bill O'Reilly," NARAL Pro-Choice America spokesperson Kaylie Hanson Long said. "Enough said."
O'Reilly has not acknowledged the allegations on his program, but denied wrongdoing to the Times, claiming that he was the target of lawsuits because of his high-visibility.
Fox News has stood by the highly-rated host. Despite speculation that he was interested in retiring in the coming years, Fox renewed his contract for an unknown amount of time earlier this year.
O'Reilly remains the top-rated host on cable news. In the first quarter of 2017, "The O'Reilly Factor" garnered its highest ratings ever, shattering the previous record for highest viewership for a television program in a quarter. On Monday, the show garnered 3.65 million viewers, over a million more than the preceding and following programs.