But I was young, and I was all the way in with Tommy. I was proud of making my own money (though I had no real concept of money). I’d recently received an enormous royalty check from sales of my debut album, so I thought I was set for life. Building a dream house with Tommy did not seem like a risk. I was selling millions of records by then. But I didn’t know that our dream mansion would come with an unfathomable thirty-million-dollar price tag. And as it turned out, my time in that house with Tommy would end up costing me so much more than money.
I did love the process of building that grand manor in Bedford. It opened up a new area of passion in me. I was finally able to give life to my childhood obsession with old Hollywood movies. Ironically, I was especially influenced by How to Marry a Millionaire, starring Betty Grable, Lauren Bacall, and Marilyn Monroe (of course). The images of palatial arched windows and glamorous, glossy floors were seared into my little-girl imagination. I made sure every room in our house was pristine and spacious, filled with air and sparkling with light. We worked closely with the designers and architects; we went over every detail together. I taught myself a lot about the styles of moldings and tiles. I became an expert in sconces—sconces, dahling! I also learned a lot about materials and would often visit various rock quarries. Though by no stretch do I like a rustic look, I do have a preference for tumbled marble on my kitchen floors. I was very particular and confident about what I liked.
Naïve as I was at the time, I decided I was going to build a great house. I had come from far too little to complain, “Oh, poor me; I have to build a mansion!” I was into it. After all, I sincerely thought I would be with Tommy forever and that the home we would make together would be just as timeless, everlasting, and spectacular as the music we were creating—behind which, of course, I was also the creative force.
And spectacular it was. We even had a ballroom. I was in my early twenties, with my own ballroom! I built a grand closet inspired by Coco Chanel’s closet in her 31 rue Cambon flat in Paris, full of opulent mirrors and a spiral staircase that led to its own shoe section. I had acquired so many shoes through all my photo and video shoots that I had to build entire walls of shelving for them. It was staggering to think that just a few short years before, I had been walking in my mother’s too-small, beat-up shoes, snow pouring in through cracks in the soles. I kept those dismal ankle boots for a while, with the intention to bronze them like baby booties, so I would never forget where I came from (as if that were even an option). In such a short time, I had gone from raggedy hand-me-downs to my own manor, complete with walls custom-built for an entire footwear collection. My faith and my fans blessed me with unimaginable riches. I was immensely grateful. But, despite that huge accomplishment, I had yet to learn that in reality, I’d just provided the design inspiration, and put up half the money, to build my own prison.
The magnificent compound I built in Bedford was just over ten miles from the village of Ossining, another quaint, wooded Westchester town, home to the most famous maximum-security prison in New York State, and possibly in the country: Sing Sing. A complex of grim stone and brick on 130 acres, landscaped with grand elm trees, Sing Sing sits formidably on the eastern bank of the Hudson River. The roller coaster–like arches of the Tappan Zee Bridge can be seen from the watchtower. In autumn, the views are breathtaking; the trees burn fiery orange, gold, and red.
Sing Sing confines about two thousand human beings. The popular terms for being locked up—being “upstate” or “up the River” or in “the Big House”—were coined at Sing Sing.
No matter how prime the real estate, how grandiose the structure, if it’s designed to monitor movement and contain the human spirit, it will serve only to diminish and demoralize those held inside. None of the irony of my proximity to the infamous prison, nor that of its peculiar name, was lost on me: jokingly, I referred to the Bedford estate as Sing Sing. It was fully staffed with armed guards, security cameras were installed in most rooms, and Tommy was in control.
While I was building Sing Sing, I thought it would be a healthy idea to have my mother and my nephews, Mike and Shawn, live closer to me. I loved the process of designing and creating a gorgeous home. While I had little freedom at Sing Sing, Tommy did support me buying a house nearby for my mother. It became a big thing for us to talk about, and he eventually understood how important it was to me to try and create something stable for my family. I later found out he secretly had security follow me around whenever I went to look at houses or run errands, but I was grateful for the small window of ignorance.
That child in me, deep down, still dreamed of a family that wasn’t fractured. I had begun to make my career dreams come true, and I thought maybe I could make us a family home—a home base, where everyone was always welcome—and I’d make my mother the head of it. I got excited about the idea of buying a home my mother would love, and I could finally afford to
