Mihhail Kaaleste was born in Estonia to a Russian family. His family changed their last name from Stoljar to Kaaleste in 1940. Kaaleste took up sports, while he was in the army. At first he did cross-country skiing in winter and decathlon in summer. He took up canoeing in 1952, to get some variety to his training routine. And he was very successful in canoeing. Already in his first canoeing competition, the Dynamo championships, he won two titles and the coaches of Soviet canoeing team convinced him to drop skiing and decathlon and concentrate only to canoeing. Already in his first major championships, 1956 Olympic Games, he was successful, winning a silver in kayak doubles with Anatoly Demitkov. To the Olympic silver he later added gold from 1957 European Championships in kayak doubles and two bronze from the 1958 World Championships in K2 1000 m (with Anatoly Demitkov) and K4 1000 m (with Igor Pisarev, Anatoly Troshenkov, and Anatoly Demitkov). He also won six Soviet championships titles in canoeing and a bronze in 4x10 km cross-country skiing in 1955. Kaaleste tried to make also to the 1960 Olympic team, but was not selected. From 1964 he started to work as a cross-country skiing coach in Dynamo Leningrad. He was also a long time head coach of biathlon team in Dynamo Leningrad. His wife Anna was a successful cross-country skier, who was ninth at the 1956 Winter Olympics in 10 km cross-country skiing and seven times Soviet champion in cross-country skiing.