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From Reagan to Trump, a speechwriter’s legacy lives on in Washington

Last week, the world lost perhaps one of the most important figures of the 20th century, but most people didn’t know it.

For those who knew him, the loss felt monumental, cataclysmic even. You could perceive the shift, through a uniquely human sensibility, in looking to an encompassing sky, that a soul of weight and force had passed beyond earthly bounds.   

At once a steadying presence and a masterful cyclone of a man, Anthony Rossi Dolan embodied the best of what it means to live a good life and to serve one’s country.  

The folk singer, cowboy-boot-wearing, Jaguar-driving journalist turned speechwriter courageously took down the mob in his home state of Connecticut before wielding his pen to confront the evils of Communism. Tony had a unique ability to pierce, condemn, and inspire through his words and deliberately crafted phrases, to move ordinary people, strike fear into dictators, and ultimately, as he would say, tell the truth.  

In the aftermath of his death, his influence on the trajectory of the Cold War has been recounted by former Reagan speechwriters, and other friends paying tribute.

Tony said that the most important thing for speechwriters to do was to live a full life. It was through living fully, embracing and experiencing the peaks and valleys of life, that you would come to find the words sitting alone in your office, late at night, clock ticking.

This pulse on humanity that Tony had was not just an abstract concept, or one applied to the masses in the audiences of his speeches. He could understand people on a deep level almost instinctively when he met them. It’s why he excelled at managing the Washington bureaucracy, but it’s also what made him beloved by all those lucky enough to meet him.

In my own case, within a few minutes of meeting me when I interviewed for my speechwriting position, Tony cut right to the chase: “So what attracts you to psychopathy?” Coming from the academic world with a research focus on genocide, I might have expected this question. But of course, no one had ever asked it before.

He was a fixture at the White House. The click-clack of his boots echoing down the halls signaled the arrival of a legendary presence. In whispered tones, staffers would note that this was Tony Dolan, Reagan’s chief speechwriter.

He knew everyone, or seemed to, even those far removed from the speechwriting shop. And he had time for everyone, no matter their rank or connections, and their parents, and their siblings, their spouses, their boyfriends and girlfriends, and whomever else they had tagging along with them.

He served all eight years of the Reagan administration, served in the George W. Bush administration, and stuck around to serve again and mentor those in the Trump administration.

Multiple generations of speechwriters benefitted from his guidance. He was as hands-on as they come, even up until this current administration, working late into the night alongside the 20-something staffers trying to keep their heads above water.

It is an understatement of the highest order to say that rare is the man in Washington who returns administration after administration to guide younger generations and serve the president without any personal ambitions for grandeur, notoriety, or accolades.  

The goal is to keep your name out of the papers, he would tell young staffers.  

He also told the young men at the White House that they had better find their girl now while the ladies would date them in their professional prime. He once ended a meeting, where I was the only woman in attendance, so I could change before a formal reception at the White House that evening. 

“You look fine,” one of the men had said. “You know nothing about women,” Tony interjected, “the lady must change.” 

He quietly picked up the tab for a date I was on having been seated at a table nearby. It is a cliche to say, but there are too many stories of his quick wit, compassion and wisdom to recount.  

He looked out for me and every other speechwriter when anyone tried to interfere with our process or otherwise inflict some kind of bureaucratic or ego-driven harm. 

It’s Shakespearean, Tony said, quoting Jeane Kirkpatrick, the downfall of those in Washington. Not Machiavellian.  

How do you adequately pay tribute to a man who always knew what to say, to his friends, to his mentees, to his colleagues, to the president, to the world? 

The obituaries will report that he had no children. Just as an onlooker may have mistaken his low profile for a lack of consequence, so too might someone unfamiliar underestimate his legacy. 

Across Washington D.C. and our nation, generations of writers make decisions every day with Tony in their ear, not just in their professional lives at the highest levels of power and influence, but in their personal and private lives as well. 

So long Tony. We will miss you.  

Amanda J. Rothschild is a former special assistant to the president and senior national security speechwriter at the White House during the first Trump administration. 

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