[2] He was the youngest of five children to Chester Henry, an itinerant Southern Baptist preacher, and Alice Verna (Johnson) Jennings.

[2] From then on he grew up in a rural atmosphere that was intolerant of African Americans and gay people; several of his cousins and uncles were in the Ku Klux Klan.

"[3] He attended Paisley Magnet School in Winston-Salem, North Carolina[2] where he did well academically, but was beaten by classmates for what they saw as effeminate behavior and attempted suicide after realizing he was gay.

[2][7] Jennings then co-founded the Gay and Lesbian Independent School Teacher Network (GLISTeN) in Boston in 1990, to address the problems facing LGBT students.

[6] In 1993, Jennings was named a Joseph Klingenstein Fellow at Columbia University's Teachers College, from which he received his master's degree in interdisciplinary studies in education in 1994.

[4] In July 2004, Jennings received the National Education Association (NEA)'s Virginia Uribe Award for Creative Leadership in Human Rights.

[9] NEA Republican Educators Caucus chairwoman Diane Lenning protested the award because—by her reading of a story in Jennings' book One Teacher in 10—she thought he broke Massachusetts law in 1988 by not reporting a sixteen-year-old gay high school student's relationship with an older man.

[10] Three days later, the caucus ousted Lenning as chairwoman over her stance against gays,[11] and later that month The Washington Times published a letter from Jennings saying the accusations were hurtful, inaccurate and potentially libelous.

[13] The incident resurfaced in 2009 as part of a social conservatives' campaign against Jennings' appointment to head the U.S. Department of Education's Office of Safe and Drug-Free Schools,[13] as well as a conference sponsored by GLSEN with the Massachusetts Department of Education in 2000 where instructors were fired for promoting the practice of fisting to underage youth.

[17] Jennings and the director of the Gay Hockey Association met with officials of the Rangers and Madison Square Garden but failed to get much action from them.

[7] On May 19, 2009, Obama administration Secretary of Education Arne Duncan announced Jennings' appointment as an Assistant Deputy Secretary for the Office of Safe and Drug-Free Schools,[5] starting July 6, 2009[20] as the third director of the office, which was established in 2002 during the George W. Bush administration pursuant to the Safe and Drug-Free Schools and Communities Act part of the No Child Left Behind Act of 2001.

"[23] As Assistant Deputy Secretary, Jennings focused on matters relating to student safety, classroom discipline and bullying.

[33] Lambda Legal's board of directors announced it has named Kevin Jennings as the organization's new CEO,[34] following a five-year stint as executive director of the Arcus Foundation,[35] a philanthropic foundation advancing social justice and conservation issues, which he joined after leading Be the Change for a year and helping launch its Opportunity Nation campaign.

Since 2015, he has been the founding board chair for the Ubunye Challenge, which uses extreme athletic events to raise funds to build schools in southern Africa.

[citation needed] Jennings received the Distinguished Service to American Education Award of the National Association of Secondary School Principals in 2007.