Appears regularly as an analyst on "Hardball with Chris Matthews" (1997) and "The Chris Matthews Show" (2002).
Named Senior White House correspondent for NBC News in February, 2001.
He was part of the NBC team covering the September 11, 2001, attacks reporting from Florida where President George W. Bush first learned of the catastrophe. He was the only television correspondent to accompany Bush to Ground Zero three days after the attacks.
In May, 2002, George W. Bush visited France to meet with French President Jacques Chirac. At a press conference, David Gregory asked of Bush, "You said in reaction to demonstrations against you and your administration during this trip in Europe that it's simply a healthy democracy exercising its will, and that disputes are positive. But I wonder why it is you think there are strong - such strong sentiments in Europe against you and against this administration? Why, particularly, there's a view that you and your administration are trying to impose America's will on the rest of the world, particularly when it comes to the Middle East and where the war on terrorism goes next?" Then, he turned to Chirac, whom he addressed as "Monsieur le President Chirac," and asked - in French - "Would you maybe comment on that?" Bush was not amused by this display of fluency. "Very good," Bush said. "The guy memorizes four words, and he plays like he's intercontinental." Gregory was surprised, possibly defensive, and definitely ready to turn the tables when he replied, "I can go on." Bush snarked in return, "I'm impressed - que bueno. Now I'm literate in two languages." Viewers of the televised segment were divided: some thought that Gregory had legitimately embarrassed Bush, while Bush's supporters that that Bush's sarcastic wit had made self-mockery of both of them.
Purchased a $2.45 million home in Washington, D.C., in October, 2005.