Some of these moments are historically humiliating, some will leave you scratching your head, and others are downright hilarious. Check out Trump’s most embarrassing moments since he first took office back in 2016. Hair mishaps Trump’s hair has provided fodder for comedians for years, and much has been written about the president’s coif. Trump’s hair usually seems frozen in place, but every once in a while the wind catches his comb-over just right and it lifts off his head. During a hurricane briefing at the White House in 2019, Axios reported that Trump said, "I got it.