Leland's mother is La Fonda Darnell. When Leland was eight 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 Dog and to bond with him. Leland thought his step-dad was his real dad. Leland lived in 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 supposedly ran the 100-meter in 9.89 seconds when he was 16, although there is no proof of this ever happening. The likelihood of this is doubtful since this time would put Leland up there with world class runners. Leland graduated high school in 1993/1994. Leland is the only one out of all of his brothers and sisters to have graduated high school. Leland was arrested at age 17 for mugging a tourist. At age 21, Leland started his own bail bonds company, "Da Kine Bail Bonds," in Kona, Hawaii after earning his bail bonds license. He also got married and had two children. A few years later the couple split.
Leland has two sons, Dakota Chapman, born March 24, 1995 and Cobie Chapman, born December 7, 2000 from a previous marriage, and a daughter, Leiah Breanna Chapman, Born on September 5, 2010, with his girlfriend, Lynette.