James Dolan, the prominent media executive and leader of Madison Square Garden sports properties, has been married twice throughout his life. Following the conclusion of his first marriage, which resulted in four children, he later entered into a relationship with Kristin Aigner, whom he married in a ceremony held in 2002. That second marriage produced an additional two sons, bringing his total number of children to six boys. Although public reports indicated that the couple experienced a separation in later years, his marital history reflects two primary, long-term unions that have shaped his personal life alongside his extensive corporate responsibilities.