The biggest car mistake I ever made: Selling Charles Bronson’s Cadillac

Bottom Line Up Front: When we are young we don’t know what we don’t know. We have plenty of time but are impatient. When older we have patience but less time. Use the past as a classroom. Study your own mistakes. Learn to extract value from the painful decisions you regret the most.

What I remember about that ’64 Cadillac.

It was beautiful. Triple Black. Black exterior, black convertible top, black leather interior.

A 1964 Cadillac Eldorado convertible. Google “Charles Bronson’s Cadillac” and it’ll come up. It broke my heart when I did.

Before you hit me with the Jon Voigt thing from Seinfeld, I had the delivery tag. It belonged to Charles Bronson and Jill Ireland rode in it.

Here’s one embarrassing part.

I sold that beautiful car because I was in the Army and had orders to China. I didn’t see how I could keep it. We were staying in my wife’s folks’ house in Baltimore. A guy came to test drive the car. I did treat the car well but it intoxicated me. I took him for a test drive. While driving around North Baltimore with the top down, I punched the accelerator and the car sprang forward.

Have you ever done something foolish— maybe on a date as a teenager, in a high school play or in a job interview— when the stakes are high? It’s an important moment and you do something so inexplicably wrong that you feel the entire deal slide off the table. You know you have lost whatever it was you were trying so desperately to achieve. That’s what happened when I punched the accelerator on that car. The potential buyer and I both felt it.

I think he drew a couple of conclusions.

First, what I did was disrespectful to the car. I have only owned two Cadillacs. One was a 1963 6-window sedan. Silver blue, cloth interior, 4 doors. Nothing fancy but what a wonderful car from when nothing fancy could still be a wonderful car. The other was Charles Bronson’s Eldorado. Most owners of old cars respect the car in a way that I think I communicated I did not. In any case I misread the situation.

I cherished and respected that car, but communicated otherwise.

Second, maybe he concluded that if I would do something like that—punch it—that I had not taken good care of the car. I regret doing that to this day. If I could meet him again I would apologize.

Other things I remember about that car.

Waiting for it to arrive. I was at my Dad’s house in Alexandria, Virginia shortly before I was supposed to PCS (Permanent Change of Station) down to Fort Knox, Kentucky. I bought the car and was waiting for it to arrive. I had found it in Hemmings Motor News and was so impressed by it that I went hard for it. I needed help to buy it so I reached out to my crazy uncle. I called him about the car. I didn’t have enough money. I had half of what the guy was asking. I offered half and he said, flatly, “That ain’t gonna buy this car.”

Pretty good response, I think. My uncle, who had a restored 1958 Ford Pickup and a 1974 Jag with a Chevy short block, gave me the money to buy the car.

The car belonged to a retired minor movie actress. She had somehow acquired it through Bronson’s estate. I was young and very innocent. I accepted on face value that it had belonged to Charles Bronson (turns out it had), so that was never an issue. I didn’t doubt that it was legitimately his car. She had gotten older and was ready to part with the car so had asked her son to sell it for her. The pictures were in Hemmings and I saw them and I called on the car. I asked all the right questions, I guess. But I was buying from Virginia. My crazy uncle offered to have his mechanic check the car out for me. We’ll call his mechanic Rick.  Rick had done a lot of high-end work for my uncle over the years.

I told the actress’s son my uncle was coming by with a mechanic to look at the car. He said, “No problem.” My uncle and Rick took it to Rick’s garage to check it out. They ran some tests. I think they ran a compression test on the engine. I had never been to Rick’s shop but at the end of the day after my uncle and Rick had returned the car to the guy who was selling it, he called me.

Is he connected?

He said, “Hey, what’s up with your uncle?”

I said, “What do you mean?”

He said, “Well, I don’t know anything about him but he’s kind of scary.”

My uncle is a lot of things, but scary is not something I think anyone had ever called him. My son has a saying, “Only bad guys should be afraid of the good guys.” I think maybe that’s how my uncle is scary. He’s one of the scary good guys. He used to provide Expert Witness testimony and once some thugs on the other side of a legal proceeding came out from New York and tried to beat him up in a parking garage and he drew a gun on them. They ran off. No doubt in my mind he’d have shot them.

“Scary how?” I asked.

There was a pause on the line.

He said, “Is he connected?”

This was before most people knew what connected meant. I only vaguely understood. I said, “What do you mean, is he connected?”

“You know. Is he with the mob?”

“The mob? Like the mafia?”

“Yeah, you know, the syndicate.”

“Like criminals? Like thugs? Of course not. Of course not. Why would you ask such a thing?”

He said, “Well, if he isn’t then Rick is. They took the car to a very nice garage. It has black and white tile floors and they put it on a lift and he just acted like he was in the mob.”

I had never thought of him like that, ever.

I got played by a slick used car salesman who lied to me.

When I sold the car I wept. It’s silly but it’s true. After I sold the car I came back to the house where my bride and I were staying in Roland Park, Baltimore. She asked if the sale had gone through. I said it had and my eyes started to fill with tears. I apologized as I wiped them away. My eyes were hot and I felt so foolish. My beautiful bride said something so wise.

She said, “No, it’s not silly to cry when you sell a car. You see, when you were in that car you were someone else. You weren’t the husband and father of a large family with lots of responsibilities. You were free. You were a different man.”

When I sold the car at a Classic Car Show in Pennsylvania a couple of months later the guy who bought it kind of tricked me. I should have been smarter and tougher but I wasn’t. I believed he really loved that car. He told me he loved it and that he was a private buyer but he wasn’t. He lied to me, but he took all the extra things I threw in with the car at a ridiculously low price because I thought he was like me and loved what I loved. I had the shop manual and some parts in an aluminum Army footlocker my father had brought back from Japan. The footlocker still had his name stenciled on it. I threw it all in as part of the deal because I thought this guy and I were going to stay in touch. Foolish.

I’ll never forget how I felt as he and his team sprayed some special treatment on that 64 Cadillac to make its paint job gleam right there. He put a sign on it, “Owned by Charles Bronson” and jacked the price up and sold it for a very large profit. With the delivery tag and all the records and my father’s footlocker in the back, of course. All while I stood there. My head was spinning.

Here’s what I learned: Although that car was valuable because of its provenance, it was even more valuable to me because of what it did for my image of myself. That car was valuable to me because of how it made me feel. In a way, the way I felt when I drove that car made me a better husband and father. Also, I had to let that car go because I thought I didn’t have enough money to keep it. When you have something valuable, dishonest men will trick you to get it away from you. Recognize the value of what you have. Don’t sell it or yourself short. Learn the value of financial strength.

Call to Action: First, study your most painful mistakes. Do this in writing and do it for only a fixed amount of time. Study, don’t wallow. If you have not mourned those mistakes, do so. Do it this way: “I will let myself feel regret and sadness for an hour, a day, a week.” Then allow yourself that. If it’s a major mistake, write out your most intense feelings on paper and then set fire to them. It’s cathartic. Second, look at your own life and take stock of what you cherish, whether it’s material, spiritual, emotional, or human. What is it worth to secure it? Have you secured it? How would it affect you to lose it? Finally, ask yourself this question: What’s the downside to being financially strong? I’ll give you a hint: there isn’t any.