The careers of male lawyers are radically altered by their experiences in the formation of families. These understudied male experiences fuel income differences, creating a highly hierarchical profession focused around a male mystique of “living large.” This study traces these processes across a 20-year longitudinal study of Toronto lawyers. We argue that time with corporate clients is a very specialized investment that is rewarded with partnership and earnings and that, among men, bears an unexpectedly unique relationship to having children, and that this specialized investment and its relationship to family are more culturally driven than biologically derived.