On September 10, 2025, Conrad Black found himself in the Oval Office with President Donald Trump when news broke of the assassination of Charlie Kirk, founder of Turning Point USA. Black, who has known Trump for over 25 years, had not seen him in person for several years prior to this visit. He has written extensively about Trump, producing around two million words that are mostly favorable, though not without critique.

As Black arrived at the White House, he received an alert on his phone about Kirk's injury from an assassination attempt. Initially, he hoped for Kirk's recovery, as he was only vaguely familiar with him and his organization. While waiting in the outer anteroom, Black observed a bustling atmosphere filled with distinguished visitors, including a prominent senator and economist Arthur Laffer, whom he had not seen in three decades.

The anteroom was lively, with people frequently entering and exiting. Black noted the professionalism and dedication of Trump's staff, who were polite and engaged. After about an hour, Black was invited to meet Trump, who appeared fit and composed. They were soon joined by Laffer for a photograph before the conversation turned somber.

Trump informed Black that Charlie Kirk had died. Black expressed his condolences, and the two men, along with Vice President J.D. Vance, who was a close friend of Kirk, shared their grief. Black described the scene as surreal, noting that he felt like an unlikely participant in such a personal moment. He observed that both Trump and Vance focused solely on their sorrow for Kirk and concern for his family, without any hint of partisanship or vengeful sentiment.

Black emphasized that the president and vice president were exemplary in their compassion, expressing deep concern over the rising political violence in the country. He remarked that their conversation was devoid of any political implications, aside from his own comment suggesting that this tragic event might encourage more civil discourse.

As the meeting concluded, Trump mentioned he needed to call Mrs. Kirk. Black left the White House reflecting on the qualities of America's leaders, despite the controversies surrounding them. He expressed a wish for eternal rest for Charlie Kirk, recognizing him as a committed and patriotic individual who made the ultimate sacrifice.