I worked for Dick Cheney. As a young man 25 years ago, I was assigned as a ‘Lead Advance Representative’ to George W. Bush’s vice presidential nominee. I traveled from Portland, Maine to Portland, Oregon with Cheney (and his family.) What follows is part travelogue, part witness to history, part realization that, while no one person can make all the difference, one person with a plan, a vision, and the will to see it through, can make those around him, and the structures within they operate, conform to their will.
Brief Obituary
Richard B. Cheney, was the 46th Vice President of the United States. He was the youngest White House Chief of Staff at 34. Over the next five decades, Cheney learned everything there was to know about how the American government worked, where it could be formed and reformed, and how it could be used to push forward a worldview that came of age as he did: Both neoconservatism and neoliberalism would reach their apogees during his time.
The Before Times
When I went to work for Dick Cheney, we were still in the salad days of the post-Cold War Pax Americana. The economy was booming, America was on top, and shortly, the outgoing president, Bill Clinton, would leave office with a 66% approval rating. Take yourself back to that time, please, because it’s important to understand how different everything was, and how easy it is for nostalgia to cloud our memories.
As we criss-crossed the country, the issues of the day were values-based, with plenty of education reform and tax cuts thrown in for good measure. By today’s standards, the Bush-Cheney 2000 ticket was downright moderate. Neither Bush nor Al Gore were proposing, or looking for, radical changes to how the world worked. It was working fine (or so we thought.)
Rose Colored Glasses
Cheney himself was nice to the junior staff. He didn’t yell or scream or carry on about this being right or that being wrong. He wasn’t capricious. He wasn’t much of a speaker, but that wasn’t his job. He gave remarks to the faithful in Davenport, Iowa and hobnobbed (as briefly as he could) with donors at fundraisers. Cheney was many things in my experience, but a glad-handing pol was not among them.
They Cheneys traveled as a unit. Rare was the trip where Mrs. (Lynne) Cheney, daughters Liz and Mary, and an assortment of in-laws or grand kids weren’t in tow. If Cheney was unlikely to make his opinion known on something operational, the rest of the clan was quick to point out what they didn’t like or wasn’t right. This dynamic was far different from what I’d been used to. Getting yelled at is part and parcel of doing advance work. Getting yelled at by the candidate’s daughter was something else. There was no answer other than, “Understood.”
Two Sides of the Coin
Portland, Maine is a great town. I’ve been there for work several times and in 2000, Maine was a battleground state. We’d set up a “Victory Rally” in the gymnasium of a local technical college. Standing outside before “game day” a Secret Service agent asked what made a ‘victory’ event. You see, we put up the banners of all the Republican candidates in the state. Then the RNC transfers money to the Maine Republican Party and they pay for the whole thing. We stick the “Bush Cheney” banner in the middle, but the campaign doesn’t have to pay for it (remember matching funds!) Non-plussed, the agent declared, “If you were in any other business, I’d be arresting you for money laundering.”
Cheney had entered executive service as Richard Nixon’s presidency was unraveling under the weight of Watergate. As David Sirota writes in his new book, Master Plan, Congress passed sweeping campaign finance legislation after Nixon left office. But senior advisors like Donald Rumsfeld and Cheney ensured their boss, now-President Gerald Ford, did as little as possible to effectuate the changes. To these early sentinels of unvarnished political power, money was speech, and any attempts to stifle its use were bad for business (literally.)
The Portland event occurred during the final week of the 2000 campaign. In those closing days, an earth-shaking scandal hit the campaign: George W. Bush had been arrested for DUI in 1976. Standing in the locker room, the team, along with musical guest Travis Tritt, huddled as senior aides gave Cheney the news. He listened, nodded and looked around. In complete deadpan he responded: “What’s the big deal? I’ve got three.”
Aside: Think of how far we’ve come in 25 years, where a long-buried DUI arrest was considered dirty pool. Today we have a criminal enterprise running the country.
Off to Washington, We Go
I spend four weeks in West Palm Beach, Florida during the 2000 recount but was recalled to Washington, DC to rejoin Team Cheney at the presidential transition operation. Most of my friends had gone to the Inaugural Committee (one big advance operation) so we didn’t have a lot to do. We ran errands, picked up the family from the FBO in Dulles, made the occasional trip to Austin, Texas where Cheney and Bush were meeting with prospective Cabinet members. I drove Rumsfeld around town for a couple of days and gathered potential appointees from the airport.
Immediately before Inauguration Day, the soon-to-be administration’s operations shifted to Blair House, the official guest residence for the White House. The President-Elect moved in and Cheney worked there, doing last-minute interviews and convening with Bush and other senior members of the new administration.
I ate a lot canapes and hung around. One day, a friend and I were standing outside Blair House on Pennsylvania Avenue enjoying the day. Over our radios we heard, “Ambulance to Blair House! Ambulance to Blair House.” Given our charge, Dick Cheney, had already suffered several heart attacks, we panicked. Staff and Secret Service agents alike rushed to the second floor. There, in an easy chair, sat Dick Cheney, head down, eyes closed, newspaper in his lap. Like something out of a cartoon, we all waited for something to happen, peering inside the door. Cheney took a deep breath and then we did.
The radio call wasn’t for the vice-president elect. A cameraman setting up an interview in a salon downstairs had collapsed.
First Row of the Balcony
I need to go out of order here a bit to illustrate my experience with how Cheney’s presence effected the White House.
In 2002, I was still doing advance, now for the president, and I was never home. Even if I was home, it was only long enough to do laundry, catch up with friends, and fill out expense reports. That I would be home, in the building, and invited to a meeting with senior staff to discuss a new initiative was rare. Convening in a conference room of the Executive Office Building, there were Assistants to the President, Deputy Assistants to the President, Special Assistants to the President, assistants to the assistants, a representative from the Vice President’s office, and a mook like me.
After 57 minutes of outlines, plans, and calendars, it was time for everyone to get back to work. Before we could, though, Cheney’s person in the room said, “The Vice President has a different view.” Imagine 30 people sighing in unison. The president’s staff hemmed and hawed for a moment. Cheney’s guy: “The Vice President will discuss it with the President directly.”
And that’s how it went.
Breaking Old Rules, Making New Rules
Before September 11th changed everything for all of us, Cheney was holding court with oil and gas executives at the White House in his role as chairman of Bush’s energy task force. This should have come as no surprise given Bush’s own connection to the oil industry, and Cheney’s stint as the boss of Halliburton, the massive energy services company.
What made this particular situation notable, however, is the White House refused to release who’d been in the meetings or what had been discussed. As presidential historian Alexis Coe noted in our recent conversation, Cheney understood he could run out the clock on the story. Even two decades ago, Washington didn’t stick to one thing very long. It wasn’t until 2007 that the Supreme Court ordered the document released.
We Live in the World Cheney Helped Create
In the hours and days after Al Qaeda’s attack on New York and Washington, Cheney and Defense Secretary Rumsfeld began making plans for Iraq. 9/11 though, would carry American security policy and morality downstream for the next two decades.
Torture, Guantanamo Bay, unrestricted drone warfare, and mass surveillance of American citizens would not end when Bush and Cheney left office. While Cheney alone couldn’t make any of the decisions that have led to the world we’re in today, his force of will, and the compliance of the Washington establishment created the necessary momentum and lubrication for things like state-sponsored torture, unrestricted drone warfare, the indefinite detention of individuals at Guantanamo Bay, and mass surveillance of American citizens.
The 2001 Authorization for Use of Military Force passed by voice vote in the US Senate and 420-1 in the US House of Representatives. It is still in force today. The Obama Administration didn’t end it. The first Trump Administration didn’t end it. The Biden Administration didn’t end it. What started as a result of a horrific terror attack nearly a quarter century ago is still in force.
Guantanamo Bay is still in use as a prison, with 15 ‘detainees’ still housed there. Despite campaign promises to do so, President Barack Obama didn’t close it, Trump never would, and Biden didn’t either.
The Iraq War resolution passed in both houses of Congress with significant Democratic support. Obama ran on opposing and ending the war. In the end, though he brought about an ‘end to combat operations,’ American troops would be in place to fight ISIS after he left office.
‘National Security’ programs devised by the National Security Agency during the Bush Administration have given way to the federal government contracting with mass-surveillance companies like Palantir to track those that might be threats to the homeland. Ironically, we all willingly carry tracking and recording devices with us 24/7; constant surveillance has become a literal appendage to Americans.
Cheney was a strong proponent of the ‘unitary executive theory’ a stance in which the President of the United States cannot be denied the ability to utilize the federal bureaucracy as they see fit. There is a direct line from Cheney to Gerald Ford, Ronald Reagan, George W. Bush and now, to Donald Trump. Decades of legal work and reworking the federal judiciary in the idea that the President of the United States is an elected monarch, have brought us to the moment where the Mad King of the Potomac is now gilding the White House and building an edifice to his own monomania. It would be ridiculous if not so dangerous.
Responsibility?
Who is responsible for the state we’re in? Dick Cheney can carry blame into eternity, but could he have done it without us? Those in positions of power, influence, and with a public forum did not stand up when the time came. Years went by without serious efforts to slow the roll of a system that was clear in its objective: We are in charge, you are not.
I look back at my own time in that world, as junior as I was, and ask if I had it to do over again, would I do anything differently? Would it have mattered? Probably not, but the question still must be asked for any of us that had the opportunity to say or do something and chose not to, whether out of belief, careerism, or fear.
We’ve run out the string on the world that was. The world as it is will soon give way to something far different and unexpected. If there is a lesson we take from Dick Cheney, it’s to ask the key question: Why? And then demand appropriate answers.
As Founding Father Ben Franklin warned: “Those who would give up essential Liberty, to purchase a little temporary Safety, deserve neither Liberty nor Safety.”




If Congress would not have abdicated almost any pretense of governing........ but I suppose that's a different column. The peoples representatives. 🤣
Awesome piece. Would be interesting to hear your perspective on whether there any positive learnings to take away from Cheney, or your time with him, or both.