Recent demographic trends suggest that grandparents may play influential roles in the lives of their grandchildren. Despite this, the role of grandparents in the lives of youth remains an understudied topic. Using data from a nationally representative group of youth aged 14 to 19 years from the 1992 Wave 2 National Survey of Families and Households, this study seeks to better understand the role of grandparents in the lives of grandchildren by examining which factors predict the quality of the grandparent–grandchild relationship and what the implications of this relationship are for youth. Key factors influencing the quality of the grandparent–grandchild relationship are distance, the parent’s relationship with both the grandparent and the child, and age of both the child and parent. Results do not support the hypothesis that grandparents influence the dimensions of youth well-being examined here.