Then there was Donald Trump. Bad typography; amateurish design; haphazard, inconsistent, downright ugly communications. When the Trump / Pence monogram was mocked for its how-did-they-miss-that salaciousness, their campaign team committed the ultimate act of weakness: they blinked and took it down without comment. The Republican convention was a gruesome and tawdry spectacle. And everything was topped off with nothing more than a red hat with a badly kerned, caps-locked slogan.
Later, filmmaker Michael Moore pointed out that where he came from, the industrial Midwest, people didn’t care about polling data or carefully calibrated social media campaigns, but they did wear baseball caps. He saw it coming. I did not.
Michael Bierut recounts the designing of Hillary Clinton’s campaign logo, and the backlash against it, in Design Observer.