“Welcome to O’Hare,” said the flight attendant on the overhead speaker as the plane touched down on a snowy day in March. It was Chicago, after all.

I had zero regrets about the Dodge Dart I rented. My usual forays into Chicagoland were in the suburbs, but that wasn’t on the docket this trip. In fact, no one knew I was here. It was a secret mission.

Many years ago I had gotten a call that one of my favorite ladies in the world was a raging addict who got caught and was currently locked up in rehab. I had no idea she was an addict. None. With my mouth agape, she unloaded on the phone call about her years of secret alcohol binges. A bottle of tequila before 10am? Just another Tuesday. Her addiction imploded her life, as she was fired from her lucrative job and forced into a day of reckoning.

“I’m coming to see you,” I said in between the tears. And I did. Before I knew it, I was on the Eisenhower Expressway heading into the heart of the city.

Whatever thoughts you have about the realities of rehab: the hospital-like corridors, inpatient gowns, a monk-like existence in a semi-private room with someone who bounced around homeless shelters – there was none of that here.

The rich lead a very different life and rehab was no exception.

The rehab place, in the middle of a skyscraper with a view of Lake Shore Drive, was more outpatient than inpatient. I met her in a private counseling meeting. She looked good, maybe a little better than the last time I saw her. We hugged and chatted with the counselor, as she explained the finer details of this terrible situation. We talked about our relationship and how to be supportive. We were going back to her living quarters a few blocks away.

“Why aren’t they housed here?” I asked the counselor. There were plenty of opportunities to grab alcohol at the bodegas or hit up someone on the street for a needle.

“They have to learn how to live with all the temptations of the world,” the counselor replied. “What better way to prepare them for that than to do it here? We drug test them everyday. If you’re positive, we kick you out.”

We left rehab central and walked to the apartments. We passed two bars. “It doesn’t bother you?” I asked. “Nope. I’m moving on.”

We paused outside a Seven-Eleven. “Wait here,” she said and disappeared inside. She returned with pouches of mint tobacco. “One addiction at a time,” she said as she placed one in her lip. Illinois was very strict about not smoking inside buildings. Nicotine was her last holdout.

The apartment was something out of a movie. Another skyscraper, the doorman greeted her like an old friend. The lobby was too pristine to sit in. “Coffee?” she asked. A coffee machine from the future was on a table. In a series of touchscreens, you could order whatever coffee creation your heart desired and it was free. Of course, I grabbed a mocha latte and we headed up to the 15th floor.

“This is home,” she said as she opened the door. My jaw once again fell to the floor. Ultra modern, with sleek natural colors, and floor to ceiling windows in the living room, the views of the city were breathtaking. My kitchen looked like one in an old single wide trailer compared to this one that fell out of a magazine spread. I heard another woman’s voice yelling on the phone behind a closed door. “That’s my roommate,” she said. “She’s a lawyer in the middle of a case. She’s an alcoholic.” Of course. This two bedroom, two bathroom joint cost more than double my mortgage and was half the size of my house. I also didn’t have access to an indoor pool and gym. Or a free coffee machine that made all my espresso wishes come true.

We chatted for awhile before I had to leave. Guests were not allowed overnight. I stayed with a mutual friend of ours to commiserate. I would be back in the morning.

Having never experienced rehab, I got my chance the next day. We met at the main center and they began their day with audio sessions of binaural beats. This helped them focus and bring clarity. I’ve found it’s very helpful to have in the background when writing something difficult.

And then I found myself in my first AA meeting, a requirement here. I sat in the circle and introduced myself when my turn came. Everyone here was highly professional: doctors, architects, lawyers. I was struck by the humanity of it all. They all had the same story: I was in control until I wasn’t anymore. I’m here because my business partners want to buy me out if I don’t get clean. These were highly educated and successful people, and if I’m being honest, one of my loved ones back home fit the bill for an alcoholic after hearing everyone talk. It was like a sucker punch to the gut. Everyone here drove luxury cars. Many had boats at the city marina. And yet, they were struggling just as much as someone living on the streets, only here they had more resources. They didn’t have to choose between basic needs and their addiction. In fact, their lifestyle almost encouraged addiction.

They had it all, but it wasn’t enough.

The Bible often talks about the difficulty of rich people getting into Heaven – more so than the poor – and I was convinced of that when I left the meeting.

I asked if I could take her to brunch and it was granted. The only rule was I couldn’t order alcohol, which of course, wasn’t even an afterthought.

The place was a short, cold walk away. It was crowded and it took us a moment to get a table, but we sat and chatted the morning away over good food. We talked about her family issues, hopes for the future, and she shared more interesting tales of rehab for millionaires. She had made friends with the upper crust of Chicagoian society, which was mind blowing to me. I was impressed with her brutal honesty about her failures, lies, and her unresolved pain from childhood which was probably at the root of this whole mess. I gave her the biggest hug before I left for the airport. I didn’t feel right leaving her, but she was a smart cookie and had the best care offered.

I stopped at ICE, a wine bar, back at O’Hare. This whole weekend had been surreal. A good Moscato made sense.

She was on of the success stories, released a month later. She managed to stay clean, but an opened can of worms included a hospital stay on a behavioral health floor a year later. I’m proud to say she worked the program and has been clean for several years.

I’d like to say she’s around the bend, but in recovery, there’s no such thing as cured. It’s always a conscious decision – a daily bread – not to use.

And I am proud of her for still choosing to stay clean.