Leland's mother is La Fonda. When Leland was 8 months old, his father Duane "Dog" Chapman better known as Dog the Bounty Hunter went to prison. While his father was incarcerated, Leland's parents divorced. He didn't see his father again until he was 8 years old when Dog gained visitation rights to see Duane Lee and Leland. It took a very long time for Leland and Duane Lee to trust and to bond with him. Leland thought his step-dad was his real dad.

 

Leland lived in Pampa Texas in his early years, but during his teen years moved to Colorado Springs. He was involved in the gang culture during his childhood. His father moved his family to Hawaii in the early 1990s. Leland's grandparents, Barbara and Wesley Chapman, later joined the family and opened up a bail bonds office on the Big Island of Hawaii. Leland graduated high school in 1993/1994 Leland is the only one out of all his brothers and sisters to have graduated high school. Leland was arrested at age 17 for mugging a tourist. When Leland was 17 years old he began to train as a boxer, kick boxer, and extreme fighter. Leland has won many competitions with the help of local boxer Sonny. At age 21, Leland started his own bail bonds company, "Da Kine Bail Bonds," in Kona, Hawaii after earning his bail bonds license. Leland works in the family run bail bonds business with his older brother Duane Lee Chapman

Leland has recently embarked on a new business venture with two of his brothers, Duane Lee Chapman and Wesley Chapman. Together they have formed Chapbros Media and have launched an iPhone, iPod touch and website talent contest application called Show Off.