Holloway previously served as police instructor and
certified flight instructor. He embarked on his legal career following his graduation from law school. He started his legal career in U.S. Navy as an officer and judge advocate, graduating from the
Naval Justice School's advanced trial advocacy course, earning certification as trial and defense counsel. He subsequently served as an
assistant district attorney. Holloway is also the legal analyst for
WSB Radio in Atlanta, GA, and has hosted and contributed to true-crime podcasts, including the podcast
Sworn and Up and Vanished. In his 2015 CNN article,
Should 11-year-olds be charged with adult crimes?, he argues against trying
juveniles as adults, highlighting the risks associated with placing them in adult prisons and suggesting alternative approaches for handling juvenile offenders and emphasizes the need for rehabilitation and alternative programs to address the underlying issues and provide a chance for young offenders to reform. In the aftermath of the
Murders of Alison Parker and Adam Ward on live TV in Virginia in 2015, Holloway has argued that employers and
HR personnel need to recognize they are “putting lives at risk” when they fail to warn subsequent employers about the dangerous behavior of their former employees. Following Trump's prosecution in 2023, Holloway criticized
Manhattan District Attorney Alvin Bragg, stating that there is nothing illegal about such arrangements or being a philanderer and that these things happen regularly. His analysis focused on Bragg's actions and decisions, prompting a range of opinions from legal professionals. Later the same day, Associated Press clarified the attacker, while apparently having ties to ISIS, was an American citizen and former military veteran from Texas who was already in the country. ==References==