After graduating, in addition to working professionally, he fell in love several times. He wed Maui Chapman in 1995. Leland, however, appeared to get sidetracked in some manner, and Maui grew distant from him, eventually divorcing him in 2005.
Her doubts were validated in 2006 when Leland was arrested. After being released from prison, he dated a different woman before getting married to Jamie Pilar Chapman in 2016. They’re still a unit. Leland gets along well with both his brothers and parents.