Trump
Ten years ago, back when Donald Trump was just a goofy incarnation of his formerly high-powered CEO image on a reality show with a memorable catchphrase ("You're fired!"), and Ivanka was a socialite as seemingly innocuous as any other girl on the gala circuit, being friendly with a Trump wasn't such a big deal. Now, however, even going so far as hosting them at your home can cost your businesses millions of dollars. Just ask Stephen Ross!
[Photo via @ivankatrump]
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