Pressing My Luck: A Doctor's Lottery Journey

By Shirley Press

In 2001, Dr. Shirley Press was your typical, hard-working pediatric emergency room doctor...until she won 56 million dollars (17.5 million take home) in the Florida Lottery with a ticket bought in the hospital’s gift shop. This stroke of luck brought with it numerous challenges as well as self-discovery.

In her memoir, Pressing My Luck, Dr. Press takes readers on a tour of her life and candidly looks back on how the lottery windfall affected it. She recalls her childhood in Camden, New Jersey growing up with parents who were Holocaust survivors, her determination to become successful, the wild 1970 summer adventure at Paul McCartney’s house and the years dedicated to practicing medicine. And despite her lottery fortune, she reveals how money didn’t shield her family from life’s adversities, such as her husband’s near fatal illness and her son’s drug addiction. With insight and candor, Dr. Press recounts her decisions, daily struggles as well as post-lottery observations on family, friends and life in general. In the end, Dr. Press can hardly believe that most of her confidence and personal growth that she thought was due to winning the Lotto could have been achieved without all the money.

• Language: English
• Publisher: Shirley Press
• Release date: Jun 19, 2013
• ISBN: 9780989406116

Shirley Press

I am a Florida-based author, physician and lottery winner. My interests are eclectic in nature...from the seemingly mundane to the strange and interesting. I ‘m currently in the process of publishing my lottery experience memoir, Pressing My Luck. When not editing or fulfilling my duties as an emergency pediatric care physician, you’ll find me sharing my books progress as well as my inspirations and thoughts on my blog http://www.shirleypress.com/blog.

Book preview

Foreword: First Impressions

When I was helping my mother move to an independent living facility we had to part with many of her things. She was going from a 2,200 square foot house to a 700 square foot apartment. At the time, I thought about what is left behind at the end of one’s life besides memories and photographs. My mother is a Holocaust survivor. Her life story is preserved in video interviews conducted by two organizations that document the lives of those who survived the horrors of Nazi Germany. These videotapes are her legacy. Her life is inspiring. While my life pales in comparison, I also would like to share and inspire. Plain and simple, that's why I've written this book.

After diagnosing otitis media (ear infection) over 15,000 times, I came to the conclusion that I am more than ready to try something new. Summoning the perseverance that saw me through medical school and residency in pediatrics, I applied myself to writing this book (although, it has actually taken me longer to finish than the four years of medical school). This work contains a lifetime of thoughts, experiences and perhaps some of my ego demanding its due after years of being suppressed by my shyness.

In a nutshell, this is my life. There are happy days, funny events, depressing and desperate times, revelations and a lot of coincidences. It’s a convoluted American dream in a lot of ways. Between the lines, I seek to find my special place and purpose in this world. One of my biggest fears in life is to be unmemorable or invisible.

Like many aspiring authors, I’ve been writing this book for much longer than I ever expected. To bend a well-known phrase; dying is easy; it's writing that's tough. Sometimes, I have ideas that evaporate before I write them down. I'm still working as a physician. I get distracted by life which consumes the time I vowed to dedicate to my book.

However, I finally got the jolt I needed when I was required to take a vision test and renew my driver's license a few years ago. As the clerk handed me my new license, I asked, When do I have to renew again?  She replied, Eight years. I was aghast. In eight years, I was going to be 66. I knew it was time to reinvent myself. I made a resolution not to waste any more time. Of course, this is impossible, but I am trying.

I considered writing a memoir before I won the lottery. There was my chance encounter with the essence of Paul McCartney, a total fantasy for a die-hard Beatles fan, though I couldn't see that it would amount to much more than a three to four page story. Then I considered writing about the Pediatric ER and learning more about my parents' early lives. However, with working long hours and raising a family, I never found the time. I thought I'd get to it when I went part-time or retired.

Then it happened. In 2001, I was your typical, hardworking, pediatric emergency room doctor … until I won 56 million dollars (17.5 million take home) in the Florida Lottery with a ticket that I bought in the hospital’s gift shop. It gave me the time needed to write and it cast a new light on everything. There have been unintended consequences to winning the lottery and the money has not prevented my family from facing despairing times. Yet the lottery has led to new experiences, such as wading into the South Florida charity scene, figuring out how to fend off scammers, meeting new people and harboring the admittedly juvenile feelings of payback that come into play. The win has also enabled me to expand my life and perspective in surprising ways.

As a little girl, I always dreamed about being rich, or rather, dreamed about not being poor. I thought if I was driven – studied hard, earned college scholarships, and picked the right career – I would be successful. And that's what happened. By the time I was 50, I had pretty much accomplished my goals, but also felt resigned that most of my major adventures were behind me. Then, my secret fantasy came true – I won the lottery. My polyester life turned to silk.

So I hope people will enjoy sharing my adventures and perhaps learn something along the way. I want the lessons learned in my life to be part of my legacy. With my writing, I hope to make a lasting impression.

1.  Ticket To Ride

As a doctor I’m well aware that the unexpected doesn’t come pre-announced. A person doesn’t wake up in the morning thinking, I’m going to wind up in the emergency room today or I’m going to have a car sideswipe me as I cross the street at lunchtime. As it turns out, the same thing is true when good fortune pulls up a seat at your dinner table.

I was aware that there would be a drawing on the night of September 5, 2001 for what was at that point the largest lottery jackpot in Florida’s history. I fully intended to buy a few tickets that day, as I did nearly every week, but I wasn’t sure I’d be able to fit it in. I worked a short shift in the ER that morning treating patients, took a mandatory course on blood borne pathogens right after that, and then had to race back to my office to deal with the mountain of paperwork that had been collecting all day.

At the time, I was the director of a pediatric emergency department and surprisingly many people were under the impression that I did nothing but attend meetings from nine to five. Besides seeing patients, the endlessly growing pile of documents to review, messages to read and calls to return attested to something very different. After I completed the course, I needed immediate documentation of my attendance so I had to take extra time after the class was over to get that from the lecturer. I really didn’t have a spot in my schedule to buy lottery tickets, but since I played the lottery so often, it seemed ludicrous for me not to participate in such an enormous jackpot.

The sprawling Jackson Memorial Hospital complex included an arcade with a variety of shops, including a gift shop that sold the tickets. I ducked in on my way back from the lecture and sighed heavily when I saw a line of around 10 people ahead of me, all waiting for the single cashier to help them out. This gift shop was never crowded, even when the hospital was very busy. It became immediately apparent that the huge lottery drawing was the reason everyone was lined up here that day.

I’m gonna get myself a gigantic house when I win, said one woman to another while they waited.

I’m gonna have steak every night, the other replied dreamily.

The man in front of them turned in their direction. I have my eyes on a Maserati. A black one with lots of chrome.

They all grinned and continued to expand on their fantasies. I could tell from their ID badges that they were workers at the hospital. A part of me wanted to join in on their musing, but I didn’t. I was wearing a lab coat and was obviously a doctor, and they probably figured I didn’t belong in the line in the first place. Most people, even those who work closely with us, are under the impression that all doctors are wealthy. Even though that’s far from true, I felt a little bit out of place.

I’m gonna get my kids back, said the woman directly in front of me. Everyone turned in her direction. She told the group that she’d lost her six children due to neglect, but that once she hit it big on the lottery, the family would be together again. That sounded better to me than throwing a few hundred thousand after a car, though the mention of neglect made me wonder if any amount of money could make that family whole.

I didn’t consider what I would do with all the cash. Since I’d never won anything in my life, and the odds of winning that night’s drawing were one in twenty million, I assumed my losing streak would continue. I just liked to play. What I did think about was everything I had to do when I got back to my office, along with wondering about crises that might have emerged in my absence. The woman behind the counter was doing the best she could, but she seemed to be moving very slowly. Twice while I was waiting, I considered getting out of the line, but I stood my ground. Once I got close enough to see that the store had York Peppermint Patties in stock that day – they’re my favorite candy – my resolve strengthened.

When it was finally my turn, I put a Peppermint Patty on the counter and asked for six Quick Pick tickets. I’d read somewhere that more people won the lottery by having the computer randomly spit out numbers than by choosing their own, so I always played this way. I stuck the tickets with my six sets of numbers in my lab coat pocket, opened the candy wrapper and headed back up to work.

As anticipated, there was a tremendous amount of work for me to attend to when I got back to my office. I literally had to squeeze in a full day’s worth of administrative duties in the few hours I had left that afternoon. The tickets as well as that evening’s Lotto drawing were soon forgotten.

When I got home, a different swirl of activity awaited me. A quick family dinner. Coaxing my teenaged kids through their homework. Relaxing in front of the television for a while. Taking care of a few household chores. At some point, the drawing for the largest lottery jackpot in Florida history happened but it was the furthest thing from my mind.

 Dr. Press, did you hear that someone from Jackson won the lottery? a nurse said to me as I walked into the clean utility room the next morning.

Wow, I said, my eyes widening. Who is it?

No one knows. The winner hasn’t come forward yet. All we know is that the winning ticket came from the gift shop.

I wondered if it could have been one of my line mates. Maybe it was the woman with the six kids. I continued to assume it wasn’t me, because I didn’t have that kind of luck. In fact, though I’d been playing the Florida lottery for as long as I could remember, I’d never had a winning of more than nine dollars.

Several others joined us at that point, and the speculation began on who it might be and what it was going to do to their lives. As the conversation continued, I tried to imagine how sudden wealth would affect someone.

That person is going to be such an oddball, I said during a lull. They’re not going to be able to fit in anywhere.

As the day went on, a rumor gained momentum that Carl in the key shop was the winner. He hadn’t come to work and this was clearly an indicator that he’d cashed in and was off scouting a beachfront mansion. When he came in a few hours later, the speculation moved on. It was fascinating to see how this story captivated my colleagues. At some point, some new information broke: the winner had bought six tickets at the gift shop yesterday.

That was the first time I started to consider the possibility that I could be the winner. Surely, I wasn’t the only person who’d bought exactly six tickets at the gift shop yesterday. Still, it narrowed down the crowd. Of course, I could have ended the mystery by checking my tickets, but I thought I’d left them at home on my desk not realizing that I had been spending the entire day with the equivalent of fifty-six million dollars in my lab coat pocket.

The hospital was swirling with activity and I wound up working late. By the time I got home, my husband and children had eaten already. I went upstairs to check my desk where I always left the tickets. The tickets weren’t where I thought I’d left them, which gave me a little surge of panic. I could not find them. I raced around the house like a cat on catnip frantically looking for the tickets. As much as I’d convinced myself that I couldn’t possibly be the winner, the chance was still there. What if I’d managed to misplace the winning ticket? I looked through my pocketbook. There were Tic Tacs, Double Mint Gum and salt packets but no tickets. I gave up and sat down for dinner, reading that morning's Miami Herald and eating my microwaved Stouffer’s frozen entrée. I mused again on the possibility of being the winner since no one had come forward to claim the gigantic jackpot and then quickly reminded myself that this kind of luck didn’t run in my family. The biggest prize any of us had ever landed was the case of baked beans my father had won many years ago at a grocer’s picnic.

During the meal, I had a fleeting thought that the tickets could quite possibly be in my lab coat. Once I finished dinner I found my lab coat hanging on the hall tree. Of course! I reached into a pocket and pulled out the ticket. Search over. They had been in the top pocket the entire time and I had not even bothered to look at them.

I got the morning paper and went through my usual ticket checking routine. I covered the last three numbers of the six rows of numbers and checked the first three against the newspaper. I did this every week, because the only way a person could be a big winner was to have these first three numbers match. Otherwise, the payouts were tiny (in other words, the kinds of payouts that I knew). Of course, my numbers never matched. However, this week was an exception. The first three numbers of the winner were 3, 9, and 10. One of my rows of numbers on the ticket started with 3, 9, and 10.

My heart jumped just a little. A fleeting thought hit. Wow, could it be? I knew the tickets were sold in the gift shop. I knew that there was one winner. I knew-- stop it -- I laughed out loud at the thought. Never, not me!

I froze; my heart was pounding not wanting to reveal the second three numbers. I chuckled again and uncovered them - 24, 33, and 35. I must have looked like a Looney Tunes cartoon character with my eyes bugging out. They were wandering left to right to left to right, focusing on the newspaper and then back to the ticket. They matched. Then I checked it again and again. My eyes weren’t playing tricks on me: the numbers in the paper matched the numbers on my ticket. I was the winner of the $56.37 million dollar jackpot!

My legs felt wobbly as I made my way down to the family room, trying to remain as calm as possible.

Um, Bill, I think I won the lottery, I said to my husband.

He looked away from the television and tipped his head toward me. You’re tired, Shirley. You didn’t win the lottery.

I had the ticket and the newspaper in my hand and I held it out to him. I’m pretty sure I did.

My daughter Sarah was sitting on the couch with him. With a groan, she got up and came over to me, taking the items from my hands. She examined both carefully and then did a double take.

Then she screamed at such a volume that I’m surprised the neighbors didn’t call the police.

She won! She won! Mom won!

When she started screaming, I started screaming, as though I hadn’t entirely believed it myself until I had a second opinion. My son Gershon got up to join us, needing to confirm this for himself. When he did, he started screaming as well. Someone listening upstairs might have thought that our family room floor had suddenly turned into a pit of snakes. That would have been a more likely scenario than the one that was actually playing out.

Bill had no choice now but to acknowledge that this was not a product of my tired eyes. He examined the paper and the ticket himself and his face went white. For the next several minutes, all he could say was, Are you kidding me? Are you kidding me?

This lightheaded moment lasted for at least fifteen minutes. Finally, though, it dawned on us that we had no idea what to do next. Obviously, we couldn’t take the ticket over to the gift shop for redemption. Something told me that they didn’t have fifty-six million dollars in their cash register. Having no better plan, we called Michael Dribin, a former neighbor and the only attorney we knew. Though we used to live only a couple of houses away from each other, we’d never really become friends. We’d say hello at the synagogue on occasion, but that was about it. As a result, it took a minute for Michael to remember us. Of course, what we told him after that guaranteed that he’d never forget us again.

Michael naturally had no experience with the procedures involved in collecting a huge lottery jackpot. However, he said he could make some calls for us and that he would get back to us as soon as he could.

We got off the phone and waited. I was rippling with energy, not sure what to do with myself. I’d had several life defining experiences like my father’s death when I was 18, graduating medical school, having children, but nothing I’d gone through in the past prepared me for something like this.

We’re going to be millionaires, I said, shaking my head in wonder.

Gershon seemed especially pleased about this. Now I can finally get my own car, said my seventeen year old. Sarah talked excitedly while Bill just seemed dumbstruck. I knew exactly how he felt.

Michael called back an hour later, though it felt as though days had passed. He told us that we had to photocopy the front and back of the ticket, put the original in a safe deposit box, and give him the copy so he could start the verification process with the state. It was too late to do any of this that night, so we had no choice but to set the entire winning-the-lottery thing aside for the rest of the night. It goes without saying that I had more than a little trouble getting to sleep. I took the ticket to bed with me.

The next morning, Bill and I arrived at the Miami Beach Public Library a half-hour before it opened. As we waited, I grew increasingly anxious. I imagined that everyone could tell that we had a massively valuable piece of paper in our possession and that there were muggers lurking behind every corner. When the doors finally opened, we dashed to the photocopy machine only to learn that we couldn’t get the thing to work. In increasingly louder whispers, Bill and I tried to coach each other through the process, but we failed. Finally, feeling horribly conspicuous, we asked for assistance. When two members of the library staff also struggled, I felt a little better. Still, I couldn’t help imagining one of these people – who were probably scrupulously honest – making a mad dash with our ticket.

A third staff member finally got the machine to work for us and we had our photocopies. If any of the people who assisted us had any idea of what we were copying, they gave no indication of it. So much for the neon sign reading new lottery millionaire I imagined flashing on and off above my head.

We secured the ticket in our safe deposit box and then brought a copy to Michael. He looked at the document as though it were a rare coin or an alien life form. This was definitely not what he thought he’d be dealing with this week when he woke up yesterday morning. It was Friday morning September 7 and the weekend was rapidly approaching.

I’ll get to work on this right away, he said. Meanwhile, don’t tell anyone about it until I find out more from the state.

How does one keep this kind of secret completely to one’s self? I couldn’t possibly do it. As soon as I got to a phone, I delivered the news to my mother and sister. My sister responded with the ecstatic screaming I’d become so familiar within the last twelve hours. 

My mother didn’t scream, though. She listened to what I was telling her very calmly and then said, Oh, I knew we would win one day. I always thought it was going to be me. It became clear to me immediately that she wasn’t talking about winning something in a vague sense; she’d genuinely imagined that one day she would win the lottery. That it had, as she put it, skipped a generation just meant that her vision had been off by the slightest bit. This fascinated me, and I’ve subsequently noticed it from many other people with modest financial means. It’s a sense that things are going to get exponentially better soon. I suppose that’s encouraging in a way, even though it’s nothing but an illusion for most. It certainly worked out for my mother.

Work that day was a complete blur. People were of course still speculating about Jackson’s big winner, and I did my best to participate in a few of these conversations to keep suspicion away from me. Fortunately, I had that ever present pile of paperwork to deal with in addition to my usual administrative duties. These gave me something else to concentrate on, and I did my best to throw myself into my work.

The next day was a Saturday and I had lunch scheduled with my friend Cheryl Levin. I’d known Cheryl for a long time, and