Craig began his track career as a hurdler at Detroit Central High School, and only later developed into a sprinter at the University of Michigan. In 1910, he won the IC4A 220 y championship, repeating this the following year.
In 1912, Craig qualified for the Olympic team and went to Sweden, where he reached the final of the 100m. A big favourite was his compatriot Donald Lippincott, who had set a World Record of 10,6 in the heats. After no less than seven false starts, Craig won the race in 10,8 – Lippincott only finished third. Craig fought out another battle with Lippincott in the 200m, edging him to win the 200 m title. Craig was not a part of the American 4 × 100 m relay team, which was disqualified and didn't medal.
In 1948, he made a return to the Olympics as an alternate on the US yachting team. Although he did not actually compete, Craig (59) carried the American flag at the opening ceremonies in London.
- In March 1911, Craig set a new record by running the 40-yard high hurdles in 5.2 seconds, breaking the prior record held by Forrest Smithson.
- In May 1911, at his last competition wearing the Michigan uniform, Craig helped the Wolverines to a third-place finish in the inter-collegiate meet. He tied the inter-collegiate record in the 100-yard dash with a time of 9.8 seconds. He also tied the world record in the 220-yard dash with a time of 21.2 seconds. The Wolverines finished the meet with 24 points, trailing only Cornell (30 points) and Yale (24-1/2 points).