This qualitative research study addressed this question: What influence did early environmental surroundings and family have on the talent development of a cohort of American speed skaters who each competed in four Olympic Games during the 1980s and 1990s? The skaters were Bonnie Blair, Dave Cruikshank, and Dan Jansen. Independent interviews with each skater uncovered rich and unique stories with common threads. Regarding environmental surroundings, all hailed from communities in the Midwest with a rich skating tradition, an oversized hockey rink or 400-m oval, a large skating club, and strong coaches and teammates. In addition, all gravitated to Milwaukee, a speed skating Mecca with ideal training facilities, where they crossed and joined paths. Regarding family, all were born into skating or athletic families and were raised by supportive and guiding parents who were involved but not pushy. Siblings also played an influential role for Blair and Jansen, who were the youngest behind long lines of brothers and sisters who were also talented skaters and who paved the way for their youngest siblings.