Press enjoyed a high-profile career in government, politics, and broadcasting that spanned more than two decades. He was chairman of the California Democratic Party, chief of staff to California State Senator Peter Behr, and director of the California Office of Planning and Research under Governor Jerry Brown. Press is an award-winning radio show host and television commentator. He has received numerous awards including four Emmys and a Gold Mic award. He was named Best Commentator of the year by the Associated Press in 1992.