by Yehudit Haspel Ben-Dak
What would you do if one day you ended up managing a $5.4 billion charitable estate, and were given carte blanche to leverage this to better the world?
While this may sound like a fairytale, it really happened to Sandor (Sandy) Frankel, a New York attorney who had the opportunity of living out precisely this dream through his famous ultra-wealthy client, Ms. Leona Helmsley. She wasn’t the only client he represented, but definitely she was the most flamboyant – and the wealthiest.
His story results from an enthralling eighteen year business relationship with Ms. Helmsley which is well examined in his memoir, ‘The Accidental Philanthropist’ which is published by Skyhorse.
Sandor Frankel’s book chronicles his journey from ‘country lawyer from a middle-class family in the Bronx’ to becoming Leona Helmsley’s personal adviser, and the ultimate executor of her will – which on her death set up the $5.4 billion charitable estate.
In a nutshell, Leona Helmsley was born Lena Mindy Rosenthal in New York to Jewish family immigrants from Poland. She dropped out of high school and changed her name four times in a short time before finally becomes Leona Mindy Roberts.
She was the second wife of billionaire real-estate and hotelier, Harry Helmsley. He was her third husband. When the couple first meet, Leona was already a millionaire in her own right from her real estate brokerage business.
Sandor Frankel met Helmsley in 1990. He had been added to her legal team at the request of the high-powered then-team leader, Alan Dershowitz.
Your first impression of her?
“I first met her when she flew up to Boston in her private 727 in early January 1990 to meet with the new team of lawyers that would be handling the appeal from her federal conviction, her state court case, and various related matters.
“She walked into the conference room dressed in obviously expensive clothing and wearing quite a bit of jewelry. Harry was with her– he was already deeply into his decline, and she paid constant attention to him. She loved him deeply. She had brought with her several cartons with dozens of sandwiches from the Park Lane Hotel, to make sure we were all fully fed. “
Back then she’d been convicted of tax crimes in that decade’s crime of the century, which led her to fire Prof. Dershowitz.
“She wanted us all to know that she was innocent. in time, I would come to agree with her”, recalls Frankel.
Name some of her dominant traits.
“Street-smart; strong-willed; could size up people pretty well; wary about people trying to use her; generous when she felt the causes worthwhile; sometimes difficult to get along with; often helped people in need.”
She was a very dominant, opinionated women but having the guts to fire a high-profile lawyer like Dershowitz?
“She didn’t like to lose. She did believe she was innocent. In her sumptuous Manhattan penthouse, I’d witnessed the wholesale bloodletting that took place when she fired Dershowitz and the rest of the team. I was the last man standing—the lawyer she asked to stay. After her conviction, people came out of the woodwork to sue her. She’d been wounded. Her time and attention were focused on keeping out, and then getting out, of jail.”
At that time Leona Helmsley was already known as bad news.
She was a favorite punching bag of the tabloid press and on constant media display for real and imagined acts of heartlessness and vulgarity. The woman who had reputedly been the “Queen of Mean” described by Newsweek as “rhymes with rich.”
For Frankel, being Helmsley’s lawyer seems sometimes like taking a supporting role in a Hollywood movie. Detailing their 18-year-long relationship, Frankel describes being fired and rehired during multiple fits of rage.
She was infamous for her explosive temper and for tyrannizing her employees who set up an alarm system that rang whenever she was on route. According to her staff, she once told her maid: ‘We don’t pay taxes. Only the little people pay taxes”.
But In 1989, it all turned on her. Helmsley was convicted of federal tax evasion and other crimes and served 19 months in prison.
In the golden times of Helmsley era the advertisements were iconic: Leona Helmsley stood dripping in diamonds at the foot of the palatial Helmsley Palace Hotel staircase. With her arms spread in grandeur, the tagline read: ‘The only palace in the world where the queen stands guard.’
A decade later, Leona’s lawyer, Sandor Frankel, recalled her striking that same triumphant pose from her advertisements, except this time she was wearing an oversized gray sweat suit and in federal prison.
In her darkest moment, Frankel remembers seeing his larger-than-life client as a ‘frightened 71-year-old inmate’ in desperate need of someone she could trust.
Not only her prison guards were talking about her in Yiddish she did not understand, and Helmsley the paranoid suspected they were spying on her, the millionaires had to borrow money to buy a cheap snake in the vending machine.
Frankel describes one moment in prison with her: “The woman sitting opposite me in the visitors’ room, now wolfing down popcorn I’d bought her from the vending machine that was the room’s sole decorative feature. She was at that moment the most maligned person on the planet.”
No wonder. A profile article in Chicago Sun-Times described her as estranged from her four grandchildren from her only son Jay, who had died of heart failure at age 42.
Did she have any friends?
“All the years I’ve known her, I don’t know a single person I would describe as a close friend. When I grew up in the Bronx my childhood friends have remained friends to this day. But we all had nothing but a baseball helmet. It cannot be replicated in the future. I think in Israel it’s different. I’m lucky I won it.
I was at social events with her. Many times, she was surrounded by “friends” who, it turned out, eventually sued her…”
Her real image compared with her projection in the media?
“I would say very broad. On the plus side: despite the way she was portrayed in the media she helped a lot of people! For a lot of her employees she helped them cover medical expenses that they sometimes could not meet, made donations and also was very kind and loving to her husband Harry. I met him when his condition had already deteriorated. But the way she treated it; not only were there nurses who cared for him she cared and insisted he sit at the dining table and eat with her as before. Even when he could not speak.
She kept him going. And it is very unusual. Obviously, she had resources 24/7 but she prolonged his life as long as possible.”
Did you get used to her totalitarian, sometimes brutal style, did you dare telling her anything related to her abuse?
“No, I didn’t like it when I saw her abuse but I didn’t tell her. Mostly speaking with her about legal matters. If there was a situation I thought she needed to hear I realized I was supposed to tell the truth, not just what she wanted to hear. After a few years with her, people always ended up telling her what she wanted to hear. I think she got used to me telling it as it is.”
Was she a wise woman?
“Over the years people were trying to outsmart her but she outsmarted them. Yes, she was smart. She had a lot of experience. She knew people were after her money. Being a very successful real estate owner and manager, she had to be tough and smart”.
Was there any time you regretted working with her?
( Laughs…) “A challenging question but no, there were no doubts. There were ups and downs. However, In my first sentence in my book I wrote: “The first time she fired me…..”
Did she have any soft moments?
“To be a real successful real estate person in NYC, you have to have some strength. You can’t be weak, otherwise you will be eaten up. She realized she was someone who people wished to go after for her money, so she had been trying to protect herself. I witnessed people who thought she had befriended, and they were very convincing but actually, she was just toying with them. She had her way of doing so.”
You became her consigliere, not just her lawyer…
“In time, she asked me to step beyond my litigation brief and I became her consigliere, taking pains not to be just another court retainer. Then I had to manage not only her legal matters, but also the relationship between us, and between her and the countless people trying to dip a pinky or a shovel into her fortune. She’d saddle me with a host of personal issues, some sufficiently urgent (in her view) to warrant 4:00 a.m. calls asking if I knew where a certain male friend of hers might be, and occasionally firing me and then checking in as if nothing had happened.
She asked me to perform many legal tasks for which I was particularly unqualified, interpreting each of my disclaimers of expertise as proof of my ability—and ultimately tasked me with drawing up a new will for her.
What gave her enjoyment except for money and power?
“Yeah…. well…I saw her interacting with her grandchildren and I think she had Naches from them. Yes, she did leave some money to her grandchildren”.
Was she really so mean or was it the image she wished to portray in the media and actually enjoyed it? How many times she was trying to fight media coverage in court?
“I don’t think she enjoyed her media coverage, but the press seemed to have an insatiable appetite for all nasty news about Leona Helmsley, so she eventually became used to the coverage and somewhat immune to it. However, there was one incident so highly personal which she found it so disturbing that she asked me to try to end it.
It was related to her only son who died from heart attack at age 42. He and her husband Harry were interred in a mausoleum in the Bronx. She wanted to sue the mausoleum because of new construction being done by the cemetery near the mausoleum. She got very angry when she saw the headline in the New York Post: “Tomb With A View”. It was a highly personal matter for her. Following a mistaken litigation path by another lawyer, I ended the embarrassment.
If she lived in the age of an aggressive social media, would it help her image for better or worse? In my opinion, her image would not have been helped by today’s social media. As I’ve mentioned, the unending appetite for negative coverage of Leona Helmsley knew no bounds, and I think social media would simply have provided additional avenues for that kind of coverage I hope that her legacy will ultimately be defined by the good that will come to the world as a result of the charitable trust she funded.”
But she did disinherit 2 of her 4 grandchildren...Do you know why?
“She never disclosed the reason…but later on it was disputed in court and they also got some funds.”
Did she talk about her only son she lost when he was just 42 years old?
“Occasionally, but it was very painful for her. I mentioned it in the book. She felt somehow responsible for his early death. When he saw a doctor, she felt he treated him differently in order to please her. Like what she would like to hear. Obviously, she had a big love for him. Just few times she spoke to me about him. “
Leona Helmsley died aged 87 in 2007. Her $5.4 billion estates included 84 properties. The Helmsley Building in Madison Avenue, a large stake in the Empire State Building, and other iconic NYC buildings like ‘The Flatiron,’ and Tudor City.
In addition to real estate holdings, Helmsley left behind $2 billion in municipal bonds, jewelry, and artwork, as well as a safe deposit box containing 299 gold coins that were wrapped in rolls of the twenties.
And there was a Maltese dog. Mrs. Helmsley would order the dog fancy food off the menu. Ten months after Ms. Helmsley’s death, the New York Times published a front-page story headlined:
“Helmsley Left Dogs Billions in Her Will.”
According to the report, there was a two-page “mission statement” in which she instructed that the entire $5.4 billion trust, which accounted for practically all of her assets, be spent on her dog Trouble’s welfare.
Frankel: “Nobody seemed to care that the story was simply wrong. In fact, in the documents establishing the Trust, Mrs. Helmsley had given the trustees complete discretion to determine which charitable purposes to support and the amount. Dogs had no entitlement at all.”
In fact, after her prison term some considered Helmsley generous in her charitable contributions. After the 9/11 attacks, Helmsley donated $5 million to help the families of New York City firefighters and police. Other contributions included $25 million to New York–Presbyterian Hospital for medical research in 2006 through a charitable trust fund. The donations eventually grew to $65 million to establish the Center for Advanced Digestive Care at the hospital in 2009
Did you come across more of her compassionate gestures?
“Yes. She did help some of her employees with medical bills when they needed it. The tabloids didn’t report about it…”
To work with uncertainty is quite challenging… A strong, opinionated woman like your client was known for sudden caprices. How do you function in such a decision-making environment?
“I called it like I saw it–that is, gave her honest answers to her questions and honest opinions when she asked. I think she was like most people in this regard: She appreciated someone being straightforward with her. She certainly dealt with enough people who told her what they thought she’d want to hear. But even though I was always straight with her, I always remembered a cardinal rule of giving legal advice: The lawyer advises, but the client decides (subject to ethical rules, of course).”
She didn’t trust many people, actually none… so why do you think she actually trusted you?
“I’d like to think she involved me in her estate simply because she trusted me—trusting people was not a character trait she had in abundance—but that may be falsely self-flattering. Maybe it was the little things: She once told me she’d noticed that when the legal team handling her criminal case would have dinner at the Park Lane on the evenings before court appearances, I’d always order an inexpensive dish while others (she remembered who) ordered lobster or filet mignon. She might have just figured I was honest—totally, or relatively, or maybe. The simpler explanation may be that she trusted nobody else, and I was the least undesirable of all the imperfect alternatives”.
She didn’t have friends, so whom she was close to?
She did leave bequests to certain people–two of her grandchildren, her brother, and her chauffeur. The trust she left to her dog was larger than nearly all of those bequests–it was so large that, after she died, we petitioned the court to reduce it, which the court did–from $12 million to $2 million, most of which went to the charitable trust when the dog died.
Did she have any political aspiration? Did she network with politicians to better her business position?
“Never in the l8 years I knew her.”
In his youth Frankel actually had considered becoming a writer, even a journalist but eventually wound-up at Harvard Law School. After evading the draft, he built a fulfilling and successful career as a trial lawyer. As Frankel puts it: “plowing through evidence and constructing a narrative out of what I’d find a lot like storytelling, but true.”
But dealing with the Helmsley estate was a life changer for Frankel.
Were you overwhelmed dealing with the wealth management of her estate when she died in 2007?
“Yes. I became an estate executer of her $5.4 billion fortune, perhaps the largest private real estate empire in the country, which I and my four co-trustees (now two, through life’s attrition) were duty-bound to give away to causes and recipients we alone would determine. It is why today, for example, literally today, I personally signed checks totaling several hundred million dollars made out to some organizations you have probably heard of and others you almost certainly have not. Very little in my life to that point had prepared me for such a role.”
Liquidating all of those properties and the assorted diamonds, cash, and other play-things of the really rich, and overseeing a vast charitable foundation funded with the proceeds of those sales was something else altogether.
“Leona Helmsley had provided the ticket that let me enter my “golden” years uniquely equipped to help make the world-, or at least a few corners of it, somewhat better.”
She wasn’t involved with Israel causes. Do you know why?
Like many American Jews, Israel was not a priority of hers. However, I’m certain she would be very pleased and proud at everything the Helmsley Charitable Trust has done for Israel.
Did she have any political aspiration? Did she network with politicians to better her business position?
“Never in the 18 years I knew her.”
The Israel Program
Helmsley had never been in Israel and never contributed herself to Israeli causes. But, surprisingly, she left her entire estate to Sandy Frankel and the other estate executers – giving them with total authority to decide how to spend her estate.
Frankel: “I am very proud of our “The Israel Program”. We have given as we speak right now over $530 million to Israel and its causes. This year will be more than $400 million, including Corona related causes. A very large portiong of the program is health related, mainly for hospitals and clinics as well as emergency grants (from North to the South) and including more than $12.5 million to Israeli hospitals dealing with Covid-19 treatment.
We have changed the physical health landscape of Haifa with the new Rambam Hospital’s Health Discovery Tower and put a lot of resources into the periphery in places like Sderot, Sapir College, Ashdod, Nahariya and more.
We have a very small operations team; it is not in Israel. They have to report to us. We do everything from here.in the US. We follow our donations very carefully. Everything is transparent. We go very often to Israel and we see eye to eye with our beneficiaries. We are very careful.
A $ 5.4 billion dollars estate to run but zero experience or knowledge!
Leona died in August 20th 2007. Frankel recalls: “After the first year regulations were very strict. We started the organization from scratch.
I didn’t have any experience with managing funds. Zero knowledge. We had to build up programs, to recruit a professional staff, select grant managers, also investment people to invest the money. We started out with altogether $5.4 billion of assets; we have already given away $3 Billion and now we now have $8 billion! Ms. Helmsley stipulated in the founding document to establish the fund that it should be a perpetual trust. We have to generate enough funds to keep going. “
She wasn’t involved in Judaism nor Israel.
“She was never in Israel. Never contributed to Israeli causes. It is actually very amazing. When she passed away, she left the entire estate to a trust she set up, her brother, driver, her dog and 2 grandchildren.
We were 5 people as executors of the trust. Her brother, her 2 grandsons, a business colleague of hers and me She gave us complete discretion what to do with the money… her brother passed away.
We are very careful about where the money goes. We work together and visit Israel very often. We follow were the money goes. It is all completely transparent. Although we have only a very small operations staff.
We always keep up the value of the money. We began with $5.4 billion in the trust, we have spent $3 billon and now as we speak, we have 8 billion dollars! The trust is perpetual according to the Helmsley estate. We have to continue to preserve the value of the money. We have financial people whose expertise is increasing money in the funds”.
In your book you describe a few anecdotes that illustrate how money talks…
“Yes. I taste the nectar of instant popularity, and I am unquestionable proof that when you control billions of dollars, you become wittier, funnier, far more profound than you’ve ever been, and always worth listening to. Friends, pseudo-friends, former friends, would-be friends, quasi-friends, friends of friends–all come knocking…
Yes, life becomes surreal. On a trip to Israel, I as invited to join then-President Peres for lunch, beginning at 1:00. Shortly before lunch, I get invited to meet with Prime Minister Netanyahu at 2:00 the same day. This is a sentence I neverdreamed I’d utter, I respond to the second invitation, but “please tell the Prime Minister I’ll be late because I’m having lunch with the President.” I pinched myself to make sure this is real.”
How come the fund has donated so much money to Israel?
“Because I am a Jew. Israel is the homeland of the Jewish people and it is necessary for their survival. And because Israel is a democracy, embracing Western values and flourishing in the midst of nearby countries’ tsunamis of wars, chaos and fanaticism and the only reliable ally of America. Israel’s contribution to the world in science, technology, medicine, the art etc. The country itself is miraculous. Investing in Israel is placing nearly can’t miss bets.”
And there is the Israeli connection after all. Sandy Frankel met his Israeli wife, Ruthie around a Manhattan swimming pool in 1974. She was an Israeli model for the high-end swimwear producer, Gottex and other clothing manufacturers. In NY she was studying at Manhattan’s Fashion Institute of Technology. Later on, she continuing to be involved with the arts. The couple have 3 children. He dedicated his memoir to his wife with warm words: “To Ruthie, still as dazzling as the day we met, and the beautiful family we’re blessed with.”
“I am always joking with my wife, what would have happened if it was a rainy day…” Frankel’s witty sense of humor is mixed in deliberately in his compelling book.