By Illinois Review
With control of Congress on the line in less than a month, Naples-based Chicago radio host Dan Proft spent part of Tuesday’s broadcast welcoming John Bolton, one of President Donald Trump’s most persistent critics.
Bolton appeared on Chicago’s Morning Answer with Dan Proft on AM 560 The Answer to discuss Iran and Islamic terrorism.
Proft introduced him as the former assistant to the president for national security affairs and author of The Room Where It Happened: A White House Memoir. The station’s official show notes and podcast description promoted the book as well.
That’s a curious credential to spotlight.
The Room Where It Happened is anything but a neutral account of Bolton’s 17 months in the Trump White House. The book portrays Trump as driven by political self-interest and delivers a sweeping criticism of his foreign policy and decision-making.
When Bolton reissued the memoir in paperback in 2024, during Trump’s presidential comeback campaign, he added a new foreword declaring that a “mountain of facts” demonstrated Trump was “unfit to be President.”
Bolton served as Trump’s national security adviser from April 2018 until September 2019, leaving after major disagreements over Iran, North Korea, Afghanistan and other foreign-policy issues. Since then, he has become an outspoken critic of the president.
And Bolton’s appearance Tuesday came with additional baggage.
In June, Bolton pleaded guilty in federal court to willfully retaining national defense information. Federal prosecutors said he used personal accounts to transmit classified information to family members who were not authorized to receive it.
Bolton had originally been indicted on 18 counts. His guilty plea to one count resolved the entire indictment. Under the agreement, Bolton faces up to five years in prison, agreed to pay a $2.25 million fine and is barred from collecting federal retirement benefits.
He is scheduled to be sentenced October 28, less than a week before Election Day.
So four weeks before the midterms, AM 560 gave morning-drive airtime to a former Trump official awaiting sentencing who has spent years publicly arguing that Trump is unfit for office. It also prominently identified him with the anti-Trump memoir that helped fuel their bitter public feud.
The interview itself focused largely on national security, with Bolton arguing that Iran’s weakened regime still poses a serious terrorism threat through proxies and operatives. But the timing of his appearance is difficult to ignore.
Republicans are campaigning to keep control of Congress and advance Trump’s second-term agenda. AM 560 markets itself as Chicago’s conservative alternative, and its audience includes many Republican voters heading to the polls in November.
Trump has spent years portraying Bolton as an overly aggressive foreign-policy hawk. Bolton, meanwhile, has continued attacking the president he once served.
Now, just weeks before the midterms, one of Chicago’s conservative radio programs welcomed Bolton back to the airwaves – with the memoir at the center of his public feud with Trump prominently included in the introduction.
