Jesse Watters has rubbed several people the wrong way because of the interviews conducted on his show, Watters' World, and the segment of the same name that he hosted for over a decade on The O'Reilly Factor. Interviewees, media, and many viewers have ill-received Watters' way of questioning people on the street.
For instance, in October 2016, during a Watters' World segment, he asked a series of racist questions to Asian Americans on the streets of Chinatown in New York City. His wildly criticized segment caused an uproar in media and was even denounced by NYC Mayor Bill de Blasio as "vile, racist behaviour."
Weeks after this controversy, Watters again made headlines for his ambush of Hampshire College President Jonathan Lash. Reportedly, Watters impeded Lash from entering his residence and continued to ambush him regarding the college's decision to lower the American flag in midst of the ongoing political distress. The local police department had to be alerted as a result.
Media has also criticized Watters for his 2015 interview with black homeless people taking shelter at Penn Station.
Watters' ambush interviews have also been quite controversial. In 2009, in the process of obtaining an interview, Watters allegedly stalked Huffington Post reporter Amanda Terkel for hours and after approaching her harassed her with questions without pre-context. In 2016, during a White House Correspondents' Association dinner afterparty, where Watters was involved in a fight with Huffington Post's Ryan Grim, Watters reportedly said, "I ambushed her because O’Reilly told me to get her, because she said some really bad shit..."