Since 1985, arts figures including Georgia O’Keeffe, Frank Capra and Ella Fitzgerald have received the National Medal of Arts while similar cultural achievement has been recognized by the National Humanities Medal, which presidents have awarded to the likes of Steven Spielberg, Anna Deavere Smith and Louise Glück. But neither of those medals has been awarded since President Trump took office, the longest gap ever and one that again draws attention to the president’s often awkward relationship with the arts.