Not Your ‘Useful Idiot’: The Pune-Born Indian American Reporter Who Gets Under Trump’s Skin

When Shirish Date reaches out to the Trump White House for comment, he doesn’t expect quotes or clarifications. He expects insults.

“Your mom did,” White House press secretary Karoline Leavitt texted the HuffPost senior White House correspondent when he asked who recommended Budapest for a now-canceled meeting between President Trump and Russian President Vladimir Putin. Moments later, White House communications director Steven Cheung sent Date the same juvenile reply.

The exchange went viral, generating headlines and social media mockery of the administration’s sophomoric response. But for Date, a veteran journalist with three decades of experience covering politics from Florida statehouses to the White House, it was just another day at the office—and proof, his editor believes, that he’s “gotten under their skin.”

A Career Built on Tough Questions

Date’s journalism career spans more than three decades, according to his HuffPost bio. He has worked at the Times-Herald Record in Middletown, New York, the Orlando Sentinel, the Associated Press, the Palm Beach Post (where he served as Tallahassee bureau chief), National Journal, and NPR before joining HuffPost.

Date’s reporting has frequently challenged powerful figures and institutions. In 2003, he won awards for a series exposing fraud and abuse in then-Governor Jeb Bush’s prized school voucher program—reporting that prompted a criminal investigation.

In 2002, his reporting about the Florida state House speaker’s hiring of an unqualified aide—a former waitress at a Tallahassee Hooters restaurant—led to him becoming the first reporter to be banned from that chamber. For Date, being banned for tough reporting appears to have been a badge of honor rather than a deterrent.

His work has also included two political biographies: “Quiet Passion: A Biography of Senator Bob Graham” (2004) and “Jeb: America’s Next Bush” (2007). He’s also the author of five novels, demonstrating a versatility that extends beyond journalism into creative writing.

The Question That Made Him Famous

But it was a single question on August 13, 2020, that catapulted Date into national prominence and set the stage for his contentious relationship with the Trump administration.

At a White House press briefing, with cameras rolling and the nation watching, Date asked then-President Trump: “Mr. President, after three and a half years, do you regret at all, all the lying you’ve done to the American people?”

Trump, visibly taken aback, asked: “All the what?”

Date repeated: “All the lying, all the dishonesty… You have done.”

Trump did not answer, instead moving on to the next question while Date waited for a response that never came.

The moment went viral, with the video spreading rapidly across social media. Date later tweeted that he had been “wanting to ask him that for five years.”

“Everyone knows the president lies,” Date wrote in the tweet. “Most people understand that he does it every day, about pretty much everything. We’ve gotten used to it. What we forget is just how corrosive it is to our democracy.”

A Target of Trump Administration Ire

Now, in Trump’s second term, Date has become what Alternet describes as a regular target of White House vitriol. According to a recent New York Times profile, “Top Trump officials, Mr. Date said, tend to reply with insults, often bundled with praise for their boss.”

He immigrated to the United States with his family in 1967, when he was just three years old. Date grew up in Waltham, Massachusetts, Rochester, New York, and Anaheim, California.

The “your mom” exchange was merely the most publicized example. When Date asked about the Budapest meeting recommendation—a serious question about a consequential diplomatic decision regarding the Russia-Ukraine war—the juvenile responses from both Leavitt and Cheung became instant internet fodder.

“I was kind of like, this is a serious war that’s going on that has killed tens of thousands of Ukrainians in their homes,” Date told the Times.

Why They Target Him

Whitney Snyder, HuffPost’s editor-in-chief, offered her theory to the Times: “Their response to [Date] was ridiculous, but it doesn’t bother us,” she said. “Maybe he’s gotten under their skin.”

Kevin Robillard, HuffPost’s political editor, explained to the Times what makes Date’s reporting particularly concerning to the administration. Date is “alarmed” by Trump “not because he’s a Republican, but rather because his actions ‘are breaks from precedent and oftentimes massive shifts in how this president is operating,'” Robillard said.

This focus on Trump’s departure from democratic norms, rather than simply partisan opposition, appears to be what distinguishes Date’s approach—and what makes his questions particularly uncomfortable for an administration sensitive to accusations of autocratic tendencies.

The Author of ‘The Useful Idiot’

Date has channeled his Trump coverage into a book. According to his HuffPost bio, he authored “The Useful Idiot: How Donald Trump Killed the Republican Party with Racism and the Rest of Us with Coronavirus,” published in 2020 and updated post-January 6.

The book captures what Date sees as Trump’s corruption of the Republican Party and his mismanagement of the COVID-19 pandemic. The title itself—”useful idiot,” a term originally used to describe naive supporters of authoritarian regimes—signals Date’s unflinching assessment of Trump’s presidency.

More Than Just Politics

Shirish V. Date was born on February 13, 1964, in Pune, India. He immigrated to the United States with his family in 1967, when he was just three years old. Date grew up in Waltham, Massachusetts, Rochester, New York, and Anaheim, California, experiencing the American immigrant story across multiple regions before finding his calling in journalism.

He graduated from Stanford University in 1985 with a bachelor’s degree in political science. That Stanford education would prove foundational for a career spent holding powerful figures accountable—from state legislators in Florida to presidents in Washington.

Date’s life extends well beyond the White House briefing room. According to his HuffPost bio, he is a bluewater sailor with 35,000 ocean miles under his belt. He undertook a two-year sailing trip aboard a 44-foot cutter with his two sons, crossing the Atlantic, sailing through the Mediterranean, and returning via the Caribbean.

Between his time covering the Florida statehouse in Tallahassee and the White House in Washington, Date logged some 15,000 nautical miles aboard his boat, Juno. This adventurous spirit—the willingness to cast off from safe harbors and navigate uncertain waters—seems to parallel his journalistic approach.

Date is married with two sons, both now adults who accompanied him on that memorable sailing journey.

This story was aggregated by AI from several news reports and edited by American Kahani’s News Desk.