He played 886 games across 16 seasons in the NBA for the Cleveland Cavaliers, New Jersey Nets, Portland Trail Blazers, New York Knicks, and Phoenix Suns.

At Yale he played NCAA basketball for the Bulldogs from 1983 to 1987, was a member of Timothy Dwight College, and earned a degree in political science and economics.

The 1999 Knicks, the first 8th seeded team in NBA history to reach the Finals, lost to the San Antonio Spurs, four games to one.

[14] After his stint with the Knicks, Dudley was traded to the Phoenix Suns for Luc Longley, participating in 53 games in the 2000–01 season.

On July 18, 2001, Dudley, along with superstar point guard Jason Kidd, was traded back to the New Jersey Nets in exchange for Soumaila Samake, Johnny Newman, and Stephon Marbury.

From 2005 to 2007, he was a volunteer assistant coach for the Lake Oswego High School boys' basketball team, where he mentored UCLA-bound star Kevin Love.

[20] In the summer of 2009, Dudley, a Lake Oswego resident, was encouraged by the Republican Party to consider a run for the U.S. House of Representatives.

[24][25] On March 6, 2010, The Oregonian reported Dudley had raised over $1 million, aided by a $50,000 donation from Nike co-founder Phil Knight.

[26] In May 2010, Dudley won 39% of the vote in a crowded Republican primary to win the GOP nomination, and prepared to face former governor John Kitzhaber in the November general election.

His primary sponsors included the national Republican Governors Association, in-state timber companies, industry trade groups, and Portland area business executives.

[8] In April 2012, Dudley announced that his family was moving from Lake Oswego, Oregon, to San Diego, California so that his wife could pursue a business opportunity.

[33] During his playing career, Dudley donated $300,000 to a non-profit organization to help pay the cost of college tuition for a class of fourth-graders at Vernon Elementary School in Portland.

[35] In October 2018, it was reported that Dudley and current United States Supreme Court Justice Brett Kavanaugh were in a bar fight in September 1985,[36][37][38][39] which involved throwing ice and a drinking glass at a man who allegedly resembled Ali Campbell of UB40.

[40][41] Through an article published in The Guardian, Campbell wrote that whomever Dudley and Kavanaugh fought was not him, and that he was not at the bar that night.