Oldham was born in Chicago and grew up in Seattle, where he attended Cleveland High School and Seattle University, with 1,530 points and 965 rebounds during his college career, after which he was drafted by the Denver Nuggets in the second round of the 1980 NBA draft.
In his NBA career, Oldham played in 329 games and scored a total of 1,455 points, playing for the Nuggets, Houston Rockets, Chicago Bulls, New York Knicks, Sacramento Kings, Orlando Magic, Los Angeles Lakers and Indiana Pacers. He was the last Bulls player to wear #33 before Scottie Pippen.
Oldham won gold as part of the US basketball team at the 1979 Summer Universiade.

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