Dick Cheney Was a Great Boss

Neil Patel
Tue, 18 Nov 2025 20:03:46 -0800
Opinion

To the rest of the world he was the vice president of the United States, but we all called him "the boss." He was the ultimate boss.

Dick Cheney was tough. That part of him is widely understood. Almost everything else is misunderstood. Working for him for eight years, the man I got to know, admire and respect was nothing like the guy portrayed in public.

As a boss, he expected a lot. If you couldn't deliver, you wouldn't be around for long. If you could, he was amazing to work for. Think of any quality you want in a boss, and Dick Cheney had it.
Updated: Tue Nov 18, 2025

To the rest of the world he was the vice president of the United States, but we all called him "the boss." He was the ultimate boss.

Dick Cheney was tough. That part of him is widely understood. Almost everything else is misunderstood. Working for him for eight years, the man I got to know, admire and respect was nothing like the guy portrayed in public.

As a boss, he expected a lot. If you couldn't deliver, you wouldn't be around for long. If you could, he was amazing to work for. Think of any quality you want in a boss, and Dick Cheney had it.

The White House can be a chaotic place. You deal with constant emergencies as the weight of the world's biggest questions looms overhead. In the midst of all that constant drama, the boss was as close to drama-free as you could get. He kept a very regular schedule and stuck to it as much as he could. He got out in front of issues as early as possible, minimizing emergencies to things truly outside of our control.

More importantly, the boss loved to spend time with his family. He didn't just allow us to do the same, he encouraged it, at least as much as jobs like ours allowed. His commitment to family was so great that Air Force Two in those days was often full of kids. The boss's grandchildren were on board, many times alongside my own. After the administration ended, I remember boarding a commercial flight with my son Charlie, who was about 4 years old. He asked if we could go sit up with the pilots. I had to explain that it wasn't allowed — Charlie had spent so much time sitting in the jump seat on Air Force Two, he didn't know any better. I started the administration with no kids and had three by the end. We worked crazy hours, but thanks to Dick Cheney, I did not miss their childhoods.

The boss was akin to a human encyclopedia on the workings of government and public policy, but he still loved to learn. For a wonk, briefing him was a true pleasure. More than that, though, we truly looked forward to our staff meetings. They would usually start with jokes. They almost always included some interesting story or lesson based on his many years of service. Then we would get to work. It was thrilling to bring someone new in and witness their transformation from terrified beginner to pleasantly shocked veteran.

It would be an understatement to say the boss had a dry sense of humor, but he wasn't beyond a practical joke. When the press started calling him Darth Vader (something, to his great credit, he truly loved), I mentioned to him that they made extremely accurate, high-end replica Vader masks. He asked me to buy him one. When we delivered it, we took pictures at his desk in the West Wing. Then, to my shock, he wore it into the Oval Office for a meeting with the president. I still have his Darth Vader mask reimbursement check.

Finally, and most importantly, Dick Cheney was loyal to his people. When Scooter Libby was unjustly prosecuted and then left hanging by the president, Dick Cheney fought for him with all he had. He made the case for a presidential pardon all the way until the final days, and even hours, of the administration.

The average tenure of a White House staffer is about two years. At the end of the Bush administration, the president had a dinner in his residence for those of us crazy enough to stay all eight. Although the VP's staff was less than a tenth the size of the president's, nearly half the people at the dinner served the boss. We loved working for him.

Sometimes lost in all the controversies that followed him, certainly by his detractors on both right and left, is the fact that Dick Cheney was an American original. Born into a lower-middle-class family in flyover country, he was such a star that he got a scholarship to Yale. He proceeded to blow that chance due to immaturity and drinking, and had to go home to dig ditches and work on power lines. Undeterred, he got his act together, graduated from the University of Wyoming and went on to become the youngest White House chief of staff in history — then a congressman, secretary of defense and ultimately vice president of the United States. He earned all that, but most countries don't give a guy like that a shot. America gave him two.

Dick Cheney started out hated by the left and ended up hated by much of the right. I don't personally agree with everything he did, but I disagree strongly with those who think he did those things with malicious intent. Most importantly, though, from my perspective, I remember the amazing memories with a truly great boss.

Neil Patel is publisher of The Daily Caller, and was staff secretary and then chief policy advisor to Vice President Dick Cheney. To find out more about Thomas Sowell and read features by other Creators Syndicate columnists and cartoonists, visit the Creators Syndicate webpage at www.creators.com.