Dropping My Friend Off to Serve Her Time

“It was a mistake,” she told me.

In February of a few years ago, I got a call from my mentor and friend, asking if I was using Jackie (not her real name) for my books at Blue Shoe. I was. He then said I should stop — that there was an issue with her and the finances at a company we had both worked for a few years prior.

“What kind of issue?” I asked.

“Expenses,” he replied.

I didn’t think much about it at the time. I was thinking a few dinners on her AmEx. Jackie and I were friends, and when I relocated to Los Angeles to run the marketing department for the company, she was more than helpful to me. She was a good friend. She put my dog down for me when I was on the East Coast, taking care of my mom’s cancer-ridden end of life. She loaded up my apartment and sent my things to me. She was there for me, and she was there for her other friends. She was a giver, always the one to pull out her credit card. She purchased tickets to the Hollywood Bowl concert that I wanted to go to but couldn’t get myself together enough to buy tickets for. 

Six months passed, and the phone rang again.

“Did you get rid of Jackie?” my friend asked.

“No, why?” I replied.

“She was indicted today and charged with embezzling more than $1.5 million. Check your books.” Then he hung up. He does that; I think he has issues with good-byes.

All I could think of is, that’s a lot of sushi dinners. I sat there stunned. I thought about the new house she’d built next to her sister’s house and how I’d thought at the time she’d really gotten her finances together. I knew she’d had financial problems in the past. She’d lost a house in the 2008 mortgage debacle and declared bankruptcy, so when she started investing in property again and living a good life, I figured she had really pulled herself out of the hole. 

I called her. She didn’t call me back.

I called her again, and she picked up. 

“I didn’t do it. It’s a mistake,” she said.

But we both knew she did do it. I told her that I knew it was true and that she would not be defined by the worst thing she ever did — or the best thing, for that matter. I said that if she was honest with me, I would do whatever I could to help her because my experience with her was that she was a giving, caring friend, and I don’t walk away from people like that. I was the only one who stood by her, which is why on April 24, 2019, I was the one who drove her to West Virginia, to Alderson Federal Prison Camp, where she would surrender herself to serve three years. It was the same prison where Martha Stewart served time in 2004.

It was a long car ride there. We decided that I would write her story for her, and maybe there would be a book at the end of this journey she was on. I began taping our conversations. Nothing was off limits; I could ask what I wanted. Recently, I listened to those tapes and thought I just might write about it all, because it’s interesting how a felon is born. This is not to be confused with how a felon plots to become a felon, which I think is rarely the case. 

When we got to the small town, we checked into the motel where we would spend the night before I was to drop her off the next morning. Then we drove over to the prison to check the place out. It was beautiful, with manicured lawns in front of old brick buildings. It looked more like a college campus than a prison. OK, the wire fencing wasn’t particularly inviting, but I recalled that picture from the tabloids of Martha Stewart at the picnic table, and thought Jackie would be fine. 

I had spoken with a person who advises people on how to survive behind bars, and she told me that Jackie would state her name to a call box and her inmate number, and after a few minutes — or a few hours — a van would come down the drive. It would look like a Frito-Lay van, but without the Frito-Lay signage. We should wait in the car, and Jackie should show no emotion because they would see us, and laughing, joking, or sobbing would not serve her well once she went through the door.

Jackie was scared out of her mind. I was curious. 

When we arrived the next day, Jackie got out of the car, walked over to the call box, and said, “I’m Jackie, inmate number X, and I’m here to turn myself in.” 

The reply was quick and angry: “Get back in the car, and wait for our van to pick you up.” It was a harsh voice — a scary voice, to be honest.

She got back in the car.

“She can’t talk to you that way! How rude! WTF!” I exclaimed, livid.

Not five minutes later, the van came down the drive, just as had been described, and Jackie calmly got out of the car and walked over to it. 

I called my friend who had warned me about Jackie, and told him about the outrageous way she had been treated at the prison.

“What did you expect? ‘Please wait, we will be down to pick up your bags shortly and show you to your room’? For God’s sake, she stole more than a million dollars and went to prison for it! What is wrong with you?”

After dropping her off, I made the twelve-hour drive back home. I had a lot of time in the car to think about it all. As I said to Jackie, I believe we are not defined by the worst thing we have done — or the best, for that matter — but rather, by the little things in between. 

Jackie is out of prison now, and I haven’t spoken to her. But I think about the whole experience and how easy it was for her to slide into felon status. I think about her initial mistaken use of her business credit card for personal expenses and her realization of how easy it was to cover it up — and how after that it was a game. A sexy, risky game of f@#$ you to those she didn’t like in management, or that is how she justified it. Voilà, she became a felon. I’m glad I went with her that day; I am hopeful she builds a new life keeping the best of what she is in sight.