Stein writes a regular column in the conservative magazines The American Spectator and Newsmax. He has also written for numerous publications, including The Wall Street Journal, The New York Times, New York Magazine, Penthouse, Los Angeles Magazine, and Barron's Magazine. He wrote a regular biweekly column for Yahoo! Finance online, with his last article dated August 7, 2009. His bestselling books (with investment advisor Phil DeMuth) include Yes, You Can Retire Comfortably; Can America Survive?; and Yes, You Can Time the Market. In 2009, he published a collection of essays, The Real Stars.
Stein was fired from his position as a Sunday Business columnist at The New York Times in August 2009 owing to a policy prohibiting writers from making product endorsements or advertising. Stein had recently become an advertising spokesman for credit information company Freescore.com and, according to a Times statement, had assumed there would be no conflict provided that he did not discuss credit scoring in general or FreeScore.com itself in his column. However, the publication felt that it would be inappropriate for him to write for them while he was involved in advertising and terminated his contract. Writing in The Spectator, Stein states his belief that the real reasons for his firing were budget cuts at the Times, his criticism of President Obama, and pressure from those critical of Expelled, who "bamboozled some of the high pooh-bahs at the Times into thinking there was a conflict of interest".
On December 28, 2009, Stein appeared on CNN's Larry King Live with Ron Paul to discuss the attempted bombing of an American plane on Christmas Day 2009. Stein said that Paul's stance that the United States were "occupiers" in Iraq and Afghanistan "is the same anti-Semitic argument we've heard over and over again." The comment started a shouting match between the two men and prompted anger from Paul supporters and those who believe Stein went too far in calling Paul's argument anti-Semitic. Stein issued an apology on December 30, 2009.
Stein is a staunch supporter of Israel. On Larry King Live in 2009, in a heated exchange with then-Congressman Ron Paul, he has referred to Paul as anti-semitic for referring to the U.S. as "occupiers" in the Arabian peninsula.