Television series have featured teachers since the first years of the medium. Connie Brooks, of Our Miss Brooks (CBS 1952–56), is among the most popular sitcom educators, and she conforms easily to the pattern of the idealized teacher, which dominated among TV series until the last fifteen years. In keeping with traditional, gendered representations, she was a spinster. In recent years, depictions of TV teachers have become more complex, such as Roland “Prez” Pryzbylewski (HBO 2002–08). At first, this was a positive development as women characters balanced a successful professional life with personal relationships, but the trend has reversed more recently. The “good” teacher on TV has become overshadowed by negative portrayals of educators who: flee in emotional distress (Mike & Molly, CBS 2010–16); behave inappropriately (Teachers, TV Land 2016–19); straddle the childish and tawdry (Those Who Can’t, 2016– ); and, are generally deplorable (Vice Principals, HBO 2016–18). Two of the most promising educator characters on television are not conventional teachers, Kenneth (Speechless, ABC 2016– ), an aide to a severely disabled student, and Issa (Insecure, HBO 2016– ) an employee at a non-profit education organization. Kenneth and Issa, both played by African-American actors, are not classroom teachers, and their status as “outsiders” to the institution of education (a concept also explored in terms of race) separates them from the downward spiral of depictions of educators on television, notably the deprofessionalization of teaching during the years since the enactment of No Child Left Behind and Common Core. This chapter examines intersectional approaches to Kenneth’s character in Speechless ranging from his positioning as a man of color, a caregiver, a “man’s man,” an honorary member of the family, and a school employee and explores these categories as a basis for the construction and performance of a character that brings more positive than negative attributes into the blighted media landscape featuring educators on television.