The image, which called Hillary Clinton the "most corrupt candidate ever," included a six-pointed star (many interpreted it to be the Star of David) and a pile of money.
Trump promptly replaced it with another version that included a circle instead, but not before the image was traced to a Twitter account known for promoting racist views.
Trump, who is highly active on Twitter and often retweets praise from his millions of followers, has come under fire many times during his presidential candidacy for engaging with Twitter users who espouse racist, sexist, anti-Semitic, or otherwise offensive views.
And outside of Twitter, he's struggled to convince voters that he doesn't sympathize with fringe conservative groups. He earned severe rebukes for his hesitation to disavow former Ku Klux Klan grand wizard David Duke.
"It's not a left-wing issue or a right-wing issue," Jonathan Greenblatt, director of the Anti-Defamation League, told the New York Times. "It's not a Democratic issue or a Republican issue. It's a matter of common sense ... It would be appropriate and timely for the presumptive GOP nominee for the White House to say unequivocally, I want nothing to do with these ideas."
Even Trump's wife Melania, who has been relatively quiet about her husband's campaign, said she wished he would be more careful in deciding who to retweet.
"Sometimes I feel that, you know, the retweets sometimes get him in trouble," she said during a Fox News interview with Sean Hannity in April. "So I say, stay away from retweets."
A Fortune Magazine analysis revealed that Trump has retweeted dozens of Twitter users who follow at least three "#WhiteGenocide influencers" and are themselves followed by over 100 such accounts. And certain members of his staff also follow racist Twitter profiles with major followings.
Here's a look at five times Trump has interacted with questionable Twitter users.
1. The Star of David image Trump tweeted was originally posted on an alt-right message board, according to Mic. It was also traced to a now deleted Twitter account, @Fishbonehead1, which has tweeted other material that disparages Jewish journalists, Muslim refugees, and black Democrats.
(Screenshot via Twitter)
2. In November, Trump retweeted an image claiming that blacks are responsible for 81% of white homicides, and that the percentage of blacks killed by police is 1%. The tweet has since been deleted.
The image cited the Crime Statistics Bureau in San Francisco, which does not exist. This happened the day after a Black Lives Matter activist was beaten at a Trump rally.
The website Little Green Footballs traced the image to the now deleted Twitter account @CheesedBrit, which featured an avatar that looked like a modified swastika and a bio claiming that "we should have listened to the Austrian chap with the little mustache."
The first retweet included a picture of a destitute-looking Jeb Bush holding a sign that read "Vote Trump." The second retweet, which was later deleted, said: "You always have the best crowds #MakeAmericaGreatAgain."
4. Trump has retweeted Jason Bergkamp at least six times. According to his Twitter bio, Bergkamp writes for Vanguard 14, a publication focusing on issues like "white genocide." He has frequently tweeted racy photos of women with the hashtag #WhiteGirlsAreMagic.
5. Neil Turner, whose bio claims he is "fighting #PoliticalCorrectness & #WhiteGenocide one tweet at a time," has earned Trump retweets at least five times.
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