The media reports the news, and what is reported is driven by peoples insatiable desire for shocking news, like failure by famous people, or heroism.  If a news outlet reported the important information like deep economic or social analysis, that news outlet would quickly go bankrupt.  Thus we live in the age of infotainment, where during the entire 2016 presidential election cycle in depth analysis of the roots of poverty, climate change, or racial unrest were never discussed and the most controversial debate analysis was about the size of Trumps hands and other outrageous and salacioius debate statements.

Trump is famous for his manipulation of the press to get himself into the news cycle (see years of Trump's birtherism proclaimations), which makes any failure on his part red meat for the infotainment centered media and news consumers, and it also means Trump is very deserving of his treatment by the press.