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In October 2015, Gragg's book 40 Days of Direction: Life Lessons From the Talented Ten was published. It relates the personal experiences of Gragg and 10 of his Commodore football teammates as African American student-athletes on the predominantly white campus of Vanderbilt University, and demonstrates how those experiences would shape their personal and professional lives, offering a blueprint for success.

Following a 10-year tenure in C-USA, the Golden Hurricane were upgraded to the American Athletic Conference (AAC) in 2014, shortly after Gragg's arrival. They won four AAC championships in the 2014 season, including conference titles in men's and women's cross country and men's soccer. In the 2013–14 season, the Tulsa basketball team won 11 games in a row and earned its first NCAA Tournament bid since 2003. They made the tournament again in 2016, losing in the first round both times.

In March 2013, it was announced that Gragg would leave Eastern Michigan University for Tulsa University. His seven years as EMU athletic director was the longest tenure since Gene Smith oversaw the department from 1986 to 1993.

On March 22, 2013, Gragg was officially introduced as the new vice president and athletic director at the University of Tulsa in Tulsa, Oklahoma. He was the first Vanderbilt Commodore football alumnus to become athletic director of a major NCAA Division I university.

On February 21, 2006, Gragg was named the new director of athletics at Eastern Michigan University in Ypsilanti, Michigan. At EMU, Gragg was responsible for an intercollegiate athletic program with 21 teams, 550 student-athletes and 80 staff members. Under his leadership, the Eastern Michigan Eagles totaled 24 Mid-American Conference team championships, 32 MAC Coach of the Year awards, 38 MAC Player of the Year honors and 164 individual MAC champions. Gragg also spearheaded construction of EMU's $3.9 million multipurpose indoor athletic practice facility.

In 1993, Gragg was hired as an academic counselor at Vanderbilt University. Soon after he was promoted to director of student life in the athletics department. From 1995 to 1997, he was director of compliance at the University of Missouri. He went on to the University of Michigan, where he was an assistant athletic director from 1997 to 2000. Gragg joined the University of Arkansas athletic department in 2000 as an associate athletic director. In 2003, he was promoted to senior associate athletic director and then deputy director.

Gragg graduated from Vanderbilt in 1992 with a bachelor of science in human development. He went on to earn a master's degree in sports administration from Wayne State University in 1999, and a doctorate in higher education administration at the University of Arkansas in 2004. He is a member of Kappa Alpha Psi fraternity.

Gragg was born and raised in Huntsville, Alabama, where he played football and basketball at Lee High School. He attended Vanderbilt University in Nashville, Tennessee, and played wide receiver for the Vanderbilt Commodores football team from 1988 to 1991. He was recruited and played for head coach Watson Brown, before Gerry DiNardo took over as head coach his senior season.

Derrick Gragg (born November 16, 1969) is an American college athletics administrator. He is the athletic director at the University of Tulsa, a position he has held since 2013. He previously spent seven years, 2006 to 2013, as the athletic director at Eastern Michigan University and six years, 2000 to 2006, as senior associate athletic director at the University of Arkansas. Gragg played college football at Vanderbilt University, lettering as a wide receiver for the Commodores for four seasons, 1988 to 1991.