Press started his broadcasting career in Los Angeles for TV stations KABC-TV and KCOP-TV. He has worked as a political commentator for CNN and MSNBC. He is best known for co-hosting CNN's Spin Room opposite Tucker Carlson, and Crossfire and MSNBC's Buchanan and Press.

Since May 2005 he has been a contributing blogger at The Huffington Post. Press also contributes blogs to the online version of Washington, D.C.'s nonpartisan newspaper, The Hill.

In politics

Press was the chair of the California Democratic Party from 1993 to 1996. He has served in different appointed positions such as a chief of staff to California State Senator Peter Behr (a Republican) and director of the California Office of Planning and Research under Governor Jerry Brown.

Radio talk show

Since September 2005, Press has been hosting a daily liberal talk radio program which is broadcast on terrestrial radio affiliates in the United States live from 6-9 AM ET. Originally syndicated by Jones Radio, the radio show is now syndicated by Dial Global. It is also heard on satellite radio, is streamed live from the show's website, and can be downloaded with a podcast subscription.

In the latest list published by Talkers magazine, Press was listed amongst the 250 most important talk radio hosts in the United States, but not in the top 100.