[1] Prior to his election as mayor, Holloway worked at the Mississippi Tax Commission for 12 years, reaching the position of senior revenue agent, and served one term on the Biloxi City Council, representing Ward 3.

During his term as mayor, he oversaw the direct financial benefit to Biloxi from casino gambling that was introduced to the area in 1992.

On August 29, 2005, Hurricane Katrina hit Biloxi causing massive damage and loss of life.

Summarizing the devastation in Biloxi left behind by Katrina, Holloway told The Sun Herald, "This is our tsunami.

Holloway said in 2004 and again in 2007: "Future generations are going to look back on this chapter in our history as a time when we made the right decisions … when we cherished and protected our culture... and we did things to improve and enhance our quality of life.