A native of the Snoqualmie Pass area of Washington, Deneen was raised in Cle Elum where his family's ranch remains his home.

[3] After his father found the flattest slope near the lodge, Deneen skied down toward his mother who was at the bottom, turning along the way as people called his name.

[3] At the age of 15, he gave up competitive horse riding to focus on skiing,[4] and began the transition from alpine to freestyle; at one point he won a downhill race and a moguls contest during the same weekend.

[6] Deneen had difficulties at the beginning of his professional career; after his World Cup debut, in which he finished 48th,[1] he was forced off the international circuit for a year due to a knee injury.

[5] Returning to the FIS World Cup circuit in January 2008, Deneen reached the podium with two straight 3rd-place finishes at Lake Placid, New York.

[8] Deneen's 2009 World Cup season was marked by inconsistent results, including 4 crashes; his finishes ranged from 3rd to 45th and 47th place within the span of one week in January.

On his final run, he landed a back layout and a twisting 720-degree spin, earning a score of 26.68 which bested the runner-up by fifty-seven hundredths of a point.