As of 2024,[update] he is the Executive Vice President of Entrepreneurship for the Greensboro Chamber of Commerce[2] Cheek's breakthrough was in the 2002 Winter Olympics in Salt Lake City, where he won the bronze medal in the 1,000 meters.

At the 2006 Winter Olympics in Turin, Italy, Cheek won the men's 500-meter event in dominating style, recording a two-run total time of 1:09.76.

That time was 0.65 seconds faster than runner-up Dorofeyev, and Cheek was the only competitor to break the 35-second mark in the competition, doing so in both of his runs (34.82 and 34.94).

[4] Near the end of NBC's coverage of the event, commentator Bob Costas noted that Cheek's application to Harvard University had not been accepted and lobbied the Dean of Admissions to reconsider the decision.

Cheek attended James B. Dudley High School in Greensboro, North Carolina, and graduated from Princeton University as a member of the class of 2011, where he studied economics and the Chinese language.