For 1969–70, the Chicago Black Hawks claimed him from Montreal on waivers, known at the time as the "intra-league draft". Esposito had a spectacular season with Chicago, posting a 2.17 GAA and setting a modern-day NHL record with fifteen shutouts, for which he won the Calder Memorial Trophy as the league's best rookie. He also took the Vezina Trophy and was named to the First All-Star team at season's end. He also was runner-up for league MVP (Hart Memorial Trophy). It was during this record setting season that he earned the nickname Tony 'O' for his shutout abilities. In 1970–71, he again proved to be one of the league's top goalies and helped Chicago finish first in the NHL's West division. The Black Hawks made it to the Stanley Cup Final, but lost in seven games to Montreal. The following season he posted the lowest GAA of his career (1.77) and shared the Vezina with backup Gary Smith. He was again selected to the NHL's First All-Star team.