Howard Bailey

Dean Howard Bailey, retired Vice President for Student Affairs at Western Kentucky University (WKU), is a trailblazing leader in student affairs whose legacy is defined by service, advocacy, and an enduring commitment to student success. Over a remarkable career spanning more than four decades, Dean Bailey has championed educational access, civil rights, and community building, impacting thousands of students, professionals, and institutions across the region. 

A native of Middlesboro, Kentucky, Dean Bailey came to WKU in 1966 as a third-generation college student, yet the first in his family to attend a predominately white institution. From his earliest days on campus, he broke barriers and blazed trails. As an undergraduate, he co-founded the first Black fraternity at WKU, Kappa Alpha Psi, and became the university’s first Black male Residence Hall Assistant. While still a student, he began his professional journey as a full-time Assistant Hall Director at Barnes Campbell Hall in 1970. He went on to earn both his bachelor’s (1971) and master’s (1973) degrees from WKU. 

With the exception of a one-year professional experience at North Carolina State University, Dean Bailey devoted his entire career to WKU. His professional path led him through roles such as Assistant Dean of Student Affairs, Dean of Student Life, Associate Vice President, and finally Vice President for Student Affairs, a position he held until his retirement in 2015. Throughout his tenure, he was widely recognized for his student-centered leadership, especially his deep commitment to underrepresented and first-generation college students. 

Dean Bailey’s impact extended well beyond WKU. For more than 30 years, he was an active and influential member of the Southern Association for College Student Affairs (SACSA). Through SACSA, he contributed to the professional development of countless emerging leaders in student affairs. Whether serving on committees, leading workshops, or mentoring young professionals, Dean Bailey brought thoughtful insight, historical context, and a spirit of service to every role. His presence at SACSA conferences became a symbol of the values the organization upholds—integrity, inclusion, and excellence. 

A respected voice on topics such as leadership, race relations, and educational equity, Dean Bailey has presented at conferences across the country. In 1995, he spent a semester in South Africa helping post-Apartheid universities rewrite their student government constitutions—an experience that further cemented his belief in the transformative power of student voice and governance. He is also a founding member of the Kentucky Association of Blacks in Higher Education and has served on the Kentucky African American Heritage Commission, the local NAACP, the U.S. Jaycees, United Way, the BGMU Board, and the Inquiry Commission of the Kentucky Bar Association. Additionally, he served a term as the elected Staff Regent on the WKU Board of Regents. 

Dean Bailey’s professional and civic life has been driven by a singular mission: to open doors and lift others. Known as both a mentor and friend to countless students and colleagues, he leaves behind a legacy built on access, dignity, and possibility. 

He and his wife, Kayla (’73, ’80), reside in Bowling Green, Kentucky, and are the proud parents of a son, Malcolm, and daughter-in-law, Melissa.