Farewell, Obi-Wan Kenobi

T ony Dolan, perhaps best known as former President Ronald Reagan’s chief speechwriter, passed away March 10 at the age of 77.

I suppose now it can be told. Tony Dolan was my old source, “Obi-Wan Kenobi,” back in the day, from 2004 to about 2011. Back then, Tony was a special adviser to former Secretary of Defense Donald Rumsfeld at the Pentagon, specializing in messaging and communications. But he was also extremely plugged in with the Bush-Cheney campaign and just about every major Republican mover and shaker in the country.

Tony had reached out to me after enjoying the initial months of campaign coverage on the Kerry Spot blog I wrote for NRO. I was (sigh) a very green 29 back then, and basked in the long conversations with an old Reagan hand who had seemingly been everywhere and done everything. Tony’s first campaign work had been for Barry Goldwater — he had gone to Yale, won a Pulitzer Prize, and climbed the ranks to become Reagan’s chief speechwriter for the entirety of his presidency. (This past January, Tony had been named the special assistant for domestic policy for the White House Domestic Policy Council under President Trump.)

Tony was a master storyteller, funny, insightful, often giggling at his own jokes and stories before he got to the punchline. When a wise mentor pops up in your life, you grab on and learn as much as you can. After a few conversations, I wanted to write about what he was telling me, and his serene confidence that George W. Bush would win reelection, and the American people would see through the 2004-era flim-flam from the likes of John Kerry, John Edwards, and Michael Moore. We agreed on the nickname “Obi-Wan Kenobi,” although I was much more of a Star Wars fan than he was. (A few months later, when Tony wanted to relay analysis from his mentor, I called that figure “Qui-Gon Jinn.”)

It didn’t take long for “who is Jim’s Obi-Wan Kenobi?” to turn into a fun guessing game in conservative media and Republican circles. I was told both Karl Rove and Newt Gingrich had been asked if it was them, and both had refused to answer. This just added to the mystery, fascination, and readership sense that whoever it was, this guy really knew what he was talking about and had the inside scoop. I steadfastly refused to confirm or deny Obi-Wan’s identity to anyone — because there was always the chance that someday someone might actually guess correctly. If anyone ever did, I’ve forgotten it, but apparently Tony was not exactly shy about either boasting or hinting that he was my source.

As the 2008 presidential cycle approached, Tony Dolan advised the presidential campaign of the late Fred Thompson. A whole lot of conservatives loved Thompson, but he indisputably lacked the cliché “fire in the belly.” After that campaign ended, I heard from other Thompson campaign staffers that Tony wanted Thompson to do what had worked for Reagan — purchase a half-hour of television time and speak directly into the camera about the challenges America faced. The other guys on the campaign liked Tony a lot — he was the loquacious, wry, garrulous grandfather you never had — but they felt like he wanted to run a 1980s playbook in a very different media and political environment.

I continued to talk to Tony and quoted him in my coverage of the 2010 midterm elections. As I wrote back then, “Several times a day, I get an e-mail: ‘So what does Obi-Wan think?’ And then, when I don’t write an update, many suspect Obi-Wan and I are pessimistic and in hiding.”

When the 2012 presidential cycle rolled around, Tony started advising the Newt Gingrich presidential campaign. This began to complicate our conversations. Tony was convinced Gingrich was the bee’s knees, and that nominating him would guarantee victory against President Obama. This meant whenever he would tell me his analysis of the GOP presidential primary, Gingrich was always running rings around the rest of the field. Polling did not concur with Tony’s rosy assessment, nor did my own instincts and perspective on that primary. We never got heated, but he would make some case that Gingrich was already on the glide path to victory and I’d reply, “Eh, I’m not so sure about that.”

In December 2011, the cover of National Review depicted Gingrich as Marvin the Martian from the old Warner Brothers cartoons, with Mark Steyn offering a scathing dismissal: “Newt writes bestselling books about government, produces DVDs about government, sets up websites about government, but he is as foreign to genuine private-sector wealth creation as any life politician. Indeed, his endurance in Washington represents one of the worst aspects of contemporary ‘public service’ — that a life in politics no longer depends on anything so whimsical as the votes of the people.”

I had no role in that issue, but Tony was infuriated — maybe you could even label him enraged over it. Apparently, he then started running around Washington saying that National Review had lost its way. And shortly thereafter, he stopped returning my emails and phone calls. I started seeing quotes in other conservative writers’ columns that sounded an awful lot like the things Tony used to tell me. It seemed I had been easy to replace.

To say I was angered by Tony breaking off his mentorship and our friendship is like saying the New York Jets have had some disappointing years lately. We had a good thing going, and I missed our conversations — even if his stories had started to get a little repetitive, and I had started to wonder if a guy in his mid-60s still had his finger on the pulse of the politics of the Obama era.

Perhaps five to ten years after we stopped talking, I bumped into him at CPAC. We had a short, curt exchange, with me raising my voice, pointing out that he walked away from me, not the other way around. Alas, that was the last time we talked.

A reader noticed that in the Dangerous Clique novels, the protagonists have an elderly mentor — a former deputy director of the CIA, nicknamed “Merlin” — who’s brilliant and has been around everywhere, but is maddeningly moody and prone to rambling about all kinds of wide-ranging esoteric and transcendent topics.

This reader asked if Merlin was “Obi-Wan” in another form. I hadn’t intentionally written the character that way, but . . . apparently the subconscious works in mysterious ways.

I’ll miss you, Tony. Even if things ended badly.