My Ride With Rudy

Over the course of my career, I sold cars in Oakland, California on three separate occasions. Oakland, to be blunt, is a sad, sad place. The amount of poverty, crime and simple human desperation makes it a tough environment in which to earn a living. That being said, nothing bad ever happened to me during those years. I saw my share of weird stuff, but I experienced no violence or robbery. But there was the time back in the early 80’s I when I went for a ride with a man named Rudy Henderson . . .

Rudy was a drug dealer. I did not know this at first. He looked nothing like the drug dealers you see in the movies. He was not very tall, but he was stocky, and it was all muscle. (I would learn later that Rudy was a weight lifter.) He dressed conservatively; partial to jaunty caps perched on his massive head. He had a disarming way about him: cool, soft-spoken, and almost gentle in his own way. He did not use foul language and seemed like a pretty nice guy all things considered.

Rudy used to launder his money through car dealerships. This is how it worked: Rudy would come in and look at a car, typically an expensive one. “I don’t have time to drive it now, but I’ll be back later to buy it”, he would say. “Could I put a deposit on it?” The time I waited on him, he handed me $5000 in cash as a deposit on a Mitsubishi Starion. He peeled the money off a massive wad of cash extracted from the pocket of his loose-fitting kakis. “Be back later,” he assured me, and as he had done to many Car Men before me, he disappeared.

Sometime later, a week maybe even two, Rudy would reappear. He would tell you that he had decided not to get the car. Could he get his deposit back? Of course the returned money would be in the form of a check. He was happy with this because depositing a $5000 check in his bank account aroused fewer questions than $5000 in cash. That was it. He had used me, but what could I do? He was an Oakland drug dealer, and nice or not, this is not the type of person you can tell to screw off.

Over the months I learned to avoid Rudy, and his attention turned to newer salesmen who were not aware of his con game. But one winter evening, he came in and everyone was busy. I had no choice but to wait on him. He had a friend with him, a nasty-looking thug with two prominent gold teeth. He said there was a car outside he was interested in. He wanted to buy it for his girlfriend. What struck me was that the car he was pointing at was a modest sedan, not the type of car that Rudy usually picked for his scam. And this time he wanted to drive the thing. Whore that I am, the greedy part of me went into gear. Heck, even drug dealers buy cars, I told myself. Maybe this was my lucky day.

Thus began my ride with Rudy.

It was 5:30 on a dark, cold winter night. An afternoon drizzle had left glistening diamonds of water on the windshields of the cars. We closed at 7:00, plenty of time for a quick demo ride and a deal. I got the keys to the car. Here is where I got stupid: I neglected to tell anyone that I was going on a drive. I did not make a copy of his driver’s license. Why bother? I would be right back. Rudy and his buddy got in front seat. I climbed into the back. We were off.

It started to go wrong as soon as we left the lot. I suggested he turn right, but he turned left. Nothing pisses off a Car Man more than a customer who refuses to follow his prescribed demo route, but what was I going to do? It was his town; let him drive where he wants, I told myself.

Rudy glanced over the back seat. “You don’t mind if I make a little stop would you?” he asked politely.

I was reluctant, but I told him that would be okay. He then proceeded to make a series of turns into an area that an Oakland cop had advised me never to venture. It seemed that this neighborhood, an old housing track that had gone to seed, had only one way in and one way out. The perfect place to get hijacked, he warned.

Rudy drove a couple of blocks then suddenly pulled over to the curb. Out of the shadows came a young man. Rudy rolled down his window. The young man handed Rudy a thick envelope. Not a word was exchanged. Rudy placed the envelope in his coat pocket and we left.

Well, that’s done, I told myself. Now we can get back to the business at hand. But when Rudy emerged back on the main road, instead of heading back to the dealership, he took the car deeper into the bowels of East Oakland.

I was not a happy camper.

Rudy made three more stops, each one farther away from the dealership. I sat in the back seat becoming increasingly paranoid; hoping this evening would not have a bad ending. I kept my mouth shut and tried to be invisible. At each stop Rudy collected an envelope, the last one from a lovely young lady who wanted to have a chat, and chat they did for about ten minutes. In this type of situation, ten minutes can seem like a lifetime. I glanced at my watch. It was 6:20. The dealership was going to close in forty minutes. We were probably six or seven miles away. I decided to speak up.

“Rudy, we need to get back. The dealership closes at 7:00.”

Rudy glanced in the rear view mirror as if suddenly remembering I was there. “Don’t worry bro. I’ll get you back.”

Rudy turned and said something to his friend. I did not hear what he said, but they thought it was really funny. He took off in the car, again heading the wrong direction. We were soon in downtown Oakland. I became more than a little nervous, not exactly scared but close. Rudy was heading in the direction of the freeway that could quickly take us back, but a block before the entrance he made an abrupt right and turned down a dark side street.

He pulled over in front of an abandoned house. The two men stared straight ahead in silence. It had started to rain again. Only the rhythmic clapping of the windshield wipers broke the silence. Someone darted out of the darkness and knocked on Rudy’s window. I jumped in my seat. Rudy rolled the window down a crack and a fifth envelope was slipped to him. Then without a word he made a U-turn, turned right, and got on the freeway heading south toward the dealership.

I was one relieved son-of-a-bitch. Rudy pulled back into the lot five minutes before closing. He pulled into the parking slot and said, “See, I got you back.” But when we got out of the car he added, “I’ve got to think about this. Thanks for the ride, bro”. And that was that. The sucker had used me for a money collection run!


Six months later I was back selling cars in Hayward. One Saturday I was standing on the showroom floor talking with my GM, Freddie Martin Jr. Freddie had lived in Oakland for many years and seemed to know everyone in that town. All of a sudden who do I see walking across the lot? I said, “Well, if it isn’t Rudy Henderson.”

Freddie turned to me, startled. “How do you know him?”

I told him briefly about how I knew Rudy and added, “He’s a drug dealer.”
Freddie laughed. “David, he’s not just a drug dealer. He’s THE drug dealer. The biggest one in Oakland. He’s not someone you want to mess with.”

I looked at Freddie. “Don’t worry, Freddie. I’d never mess with Rudy Henderson.”

A few months later Rudy got busted. It was on the front page of all the newspapers, the leadoff story on the nightly news. Rudy was a big deal indeed; a mansion in the Oakland hills, another out in the country. He went to jail for a long time. Oh, did I mention that they confiscated several very expensive cars from his estates?

Well at least someone had made some money on him.


Note: In 2002 Rudy Henderson was released from prison. In December 2006 he was found in a car—shot to death. For more information, click on the link below.


ttp://www.sfgate.com/cgi-bin/article.cgi?f=/c/a/2006/12/05/BAGV1MPFM21.DTL