Willie attended San Jose Normal School (now San Jose State University) before transferring to Michigan. He was a two-way player for the Wolverines, excelling at both running and passing. He was also a superb punter and kicker.

Heston was a consensus All-American in 1903 and 1904. He was also named the captain of the 1904 team. In his four years at Michigan, Heston scored 72 touchdowns, which is still a school record. He also rushed for 2,339 yards and passed for 1,003 yards.

After graduating from Michigan, Heston played professional football for the Canton Bulldogs in 1905. He suffered a broken leg in his first game, and this ended his playing career.

Heston then turned to coaching. He was the head coach for Drake University in 1905 and North Carolina College of Agriculture and Mechanic Arts (now North Carolina State University) in 1906. He then returned to Michigan to practice law. Heston was inducted into the College Football Hall of Fame in 1954.