The reason this came about is that Hicks connected with Trump family when she worked closely with Ivanka Trump while employed at Hiltzik Strategies, a political and entertainment PR firm, run by Matthew Hiltzik.
One interesting thing is that before starting to work for The Donald's campaign, Hicks deleted and scrubbed her entire social media profile (FB, Twitter, even LinkedIn). She is still employed by Trump Organization. Her father, former high-ranking Ogilvy executive, is now PR spin doctor for NFL's top nincompoop Roger Goodell.
Another interesting thing is who Matthew Hiltzik and his PR firm has been working for in politics for decades — almost exclusively Democrats (rare exception was Glenn Beck, which he "inherited" from his father George Hiltzik, then a PR executive at Ogilvy & Mather) and particularly Hillary Clinton, including being a liaison to Jewish community in her Senate run in 2000, and Eliot Spitzer and Chuck Schumer in their 1998 campaigns. When he is not taking a sabbatical for political campaigns, he works as a PR man, spokesman and a liaison to Democratic Party for Harvey Weinstein (of Weinstein Brothers and formerly of Miramax media company.) Among others, he also represented Katie Couric, Alec Baldwin, Annie Leibovitz and Don Imus.
Profile of public relations guru, Matt Hiltzik
That's the political shop / environment where Ivanka Trump and Hope Hicks have met and worked together; soon after Hicks was hired by Trump Organization to be on Ivanka's staff. Ivanka is also a friend of Chelsea Clinton, which is not surprising, considering how much money Donald contributed to Hillary and their friendly relationship.
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Good Reporting! Why didn’t I know about this before? All that scrubbing. All those 16 degrees of not-actual-separation. This whole Trump thing gets curiouser and curiouser.