The Private Struggle of a Public Woman

To Orange County society, Debbie Simon had it all—beauty, wealth, family, friends, and a landmark Newport Beach address. But in the desperate months before her death last year, she lost what mattered most.

On a sweltering day in late August 2009, Debra A. Simon called her friend Rosalie Puleo with an unusual request: Could Puleo come over and help her clean out her closets?

They were an unlikely pair. Debbie lived in a stately Harbor Island home once valued at more than $30 million, a hot spot for high-society fundraisers for the Orange County Performing Arts Center and Hoag Memorial Hospital Presbyterian. Puleo was a single mom who’d bonded with Debbie over their mutual Italian-Irish ancestry, childhoods in New York, and a shared charitable commitment to Hoag. They had become close friends since Debbie moved to Orange County in 2001, so Puleo went.

She found her friend upset, convinced she was about to be evicted from the 12,000-square-foot, 10-bedroom,
12-bath French-style estate built on property once owned by financier Howard Ahmanson, founder of the former Home Savings of America.

Puleo knew things were bad; Simon had shared with her and a few other friends the details and endless frustrations of her long and ongoing divorce from fashion industry titan Arnold Simon. The home had been for sale since the previous year, but the real estate market had crashed and a buyer still had not been found. Plus, according to court records, Debbie’s husband had not paid spousal support for much of 2008, and she’d told friends it had forced her to cut back on everything, including her electric bill. She often turned off the massive home’s air conditioning.

“We were dripping sweat for eight hours, sorting through her clothes, trying to determine what to keep, what to give away, and what might be sold,” recalls Puleo.

It was an oddly desperate scene, considering the setting, but few realized just how desperate.

Two weeks later, in the late afternoon of Sept. 10, 2009, Debbie was found hanging by a heavy-duty extension cord tied to the second-story balustrade in her mansion’s foyer. She was alone at the time, and apparently left no note. Debbie’s death devastated her children, her parents, her siblings, and her friends, and it shocked Orange County’s high society. It also raised a troubling question:

How could someone who seemed to have it all come to such a sad, lonely end?

Debbie’s entrance into Orange County society eight years before was a perfect example of the gravitational force of money, and it obscured the modest life she’d led till then.

Just 53 when she died, the mother of three who was known for her industrious nature had traveled a long and enviable road, from a middle-class upstate New York childhood to a lavish life at the pinnacle of Newport Beach society. As an 11-year-old, the daughter of Frank and Kay Purritano already was earning money by cleaning houses. She often shared stories of her childhood in Troy and Latham, claiming to be an awkward adolescent and the dutiful oldest sibling responsible for her sister and brothers, including Marie, Frank, Joe, and Michael. But the girl who enjoyed climbing trees and playing touch football blossomed into a young woman of striking beauty.

Her looks led to a modeling career at age 12 and a series of beauty pageants that culminated with a 1974 state title at 18. After receiving her crown, Debbie set out to make her own way, taking classes at a local business school.

At 20, she was waiting tables in a New York restaurant when she met James Stone, who became her first husband. He was handsome and sweet, and he made her feel loved and protected. Neither was making much of a living, and two seemed a better bet against the world than one. But they were unprepared for the challenges of marriage. The union, which produced daughter Lauren, lasted less than three years.

Debbie then sought work in the New York fashion industry, a natural for the former beauty queen. She landed a secretarial job with the house of Bill Blass and eventually was promoted to account executive, selling the iconic American designer’s lines to high-end retail outlets nationwide. That’s how she met Arnold H. Simon.Arnie wasn’t a rich man when he and Debbie met. He owned a relatively small business selling children’s pajamas and T-shirts when their love affair began. They were married on Feb. 2, 1985, and signed a prenuptial agreement that suggests their relatively modest circumstances at the time. It provided that in the event of a divorce, Arnie would pay Debbie $250 a month for a period equivalent to half of the duration of their marriage. She also would get $25,000 as a property settlement.

Making their home in Saddle River, N.J., the Simons welcomed sons David in May 1985 and Scott in November 1989.

As revealed in court records, the family’s rocket ride began after Arnie’s business acquired licenses to manufacture popular brands of clothing, including Calvin Klein. In 1997, Arnie cashed in, selling his interests, consisting primarily of Designer Holdings Ltd., to clothing giant Warnaco for $365 million. Of that, Debbie, who had helped with the business, received $10 million. Arnie then began investing in real estate and collectible automobiles.

The family moved to Newport Beach four years later, in 2001, although much of Arnie’s professional life was still focused in New York. Debbie threw herself into Orange County’s social whirl. Her life here was marked by prominent displays of generosity as, again and again, she hosted charitable events at her mansion and worked to steer money from the county’s philanthropists toward her favorite causes.

Terry Dwyer, president of the Orange County Performing Arts Center, credits Debbie with helping the center raise millions as a member of the Angels of the Arts Support Group since 2002: “Debbie was a gracious and generous member of the center’s family. She opened her home to Angels of the Arts and Candlelight Concert events and planned trips for Angels donors. She also served on the Candlelight Concert Committee helping raise nearly $1 million each year in support the center’s artistic and education programs.”

But she didn’t become a leading light of Newport society by attaching herself only to Orange County’s richest; many of her friends here were not privy to her level of wealth. In a way, she led two lives: the glamorous and sexy society hostess, dressed to impress at every major event, and the big-hearted, down-to-earth former tomboy with an infectious laugh and a tendency to hug everyone like she meant it.

And why not? She awoke each day in a home with a pool, more than 300 feet of waterfront overlooking the harbor’s main channel, and docks for the family’s 39-foot boat and various other watercraft. On chilly days, she could warm herself by any of six fireplaces or otherwise enjoy a residence that included a library, a butler’s pantry, staff quarters, an elevator, and an underground eight-car garage. The Simons paid $14 million for it in 2001.

While Newport Beach in many ways adheres to conservative, small-town American values, money can trump any and all barriers. Pedigree matters little. And with their opulent home and Debbie’s passion for entertaining, the Simons had made the grandest entrance imaginable.Inside the mansion, though, things were unraveling. The 15- and 11-year-old boys were launched into the world of big-money Newport Beach teenagers. Their situation was complicated by tension between their parents. According to court records, the Simons—who had separated in 1999-2000, before their move west—had done so again in 2001-02. Arnie admitted in one divorce case filing that he “dated other women and spent money on them during these periods of separation.”

Debbie finally filed for divorce in 2005, listing July 4, 2003, as the date of separation. She confided to one friend: “Why is he doing this to me? I was his wife for 20 years and gave him two beautiful sons. I don’t deserve to be treated this way.”

Reached by telephone in New York for this story, Arnie declined to comment, saying only that, “Debbie was a lovely woman. The entire family is devastated by our loss.”

Things got more desperate for Debbie in September 2007, when younger son Scott, who was 17, nearly died. Like his older brother, he had moved back to New Jersey, but it’s unclear whether they were living with their father in Saddle River. Medical records indicate Scott “suffered cardiac arrest … following a drug-related incident.” He remained in a coma for four months, and still has health problems.

Debbie continued to build her new life in Orange County, pushing herself into the public spotlight with her big money, generous spirit, and self-deprecating humor about everything from her hair extensions to her cleavage. She made friends outside her high-society network, including Puleo and Cheryl Fisher, a floral designer who describes herself as Debbie’s best friend.

But the divorce case began to resemble the 1989 movie “The War of the Roses,” with both parties hiring some of the highest-powered—and most expensive—divorce lawyers in Southern California. Court records contain more than 1,800 filings by the two parties. “This case is one of the most contentious and acrimonious family law actions experienced by counsel,” wrote one of Debbie’s attorneys.

Court records show she initially asked for $750,000 a month in spousal support. The prenup, her attorneys argued, was “unconscionable” since “it is impossible that support of $250 per month could come anywhere close to maintaining any semblance of these parties’ lavish lifestyle.” In February 2005, after numerous court hearings during more than six months, Orange County Superior Court Judge Linda Lancet Miller ordered Arnie to pay Debbie temporary alimony of $120,000 a month and to keep up the mortgage on the Harbor Island home. Debbie withdrew her request for child support before that ruling, and the judge said she could meet any other needs from the almost $50,000 a month in income she was making on $14 million in bonds.

The mansion became a sore spot. California title records for the estate show $10 million in mortgage liens on the property, although an exhibit in the divorce files shows an amount closer to $6 million as of August 2007. The title was in the name of Daks LLC, an entity controlled by Arnie. Debbie clearly wanted to remain in the Harbor Island home, and in one court filing Arnie’s attorneys charged that Debbie refused to consider selling it “knowing full well that Mr. Simon could not continue to afford to maintain it, which resulted in Daks having no alternative but to go into bankruptcy.” Regardless of the reasons, the couple did not put the home up for sale until 2008. Asking price:$38.5 million. If it had sold anywhere near that amount, and assuming the couple would divide any profits in the divorce resolution, Debbie surely would have been able to live comfortably. But the economy had begun its downturn and months dragged by without a sale. After a year, the price was reduced to $32.6 million.

To smooth the way for a divorce settlement, Arnie had agreed in July 2006 to drop his effort to enforce the prenup. But by the time the case went to trial before retired Judge Richard E. Denner in January 2008, the hostilities had intensified. Debbie discovered that Arnie had fathered a child with another woman during their marriage. One of Arnie’s attorneys suggested in a court document that “the discovery of this was, most assuredly, the straw that broke the camel’s back in Mrs. Simon’s mind during the litigation.” Accusing her of a “vendetta,” Arnie insisted he had had the affair during one of their separations.

Arnie paid no spousal support between March and November 2008. After Debbie asked the court to cite him for contempt, Arnie said he’d run out of money, having forked out $5.9 million in spousal support since the divorce filing. He also claimed in a 2008 divorce trial brief that the cost of caring for Scott was approximately $600,000 a year more than the amount covered by insurance, and that Debbie was paying none of it.During that period, Debbie clearly was struggling. She cried often and started cutting back on everything. Debbie’s concerned girlfriends came by on many nights just to keep her spirits up, sometimes staying until she fell asleep. Debbie began enlisting friends to help clear out the house, including the home’s wine cellar and the storage areas around the docks. It’s not clear whether she was trying to sell those assets, or simply preparing to move. Looking back, Puleo raises another possibility: Could Debbie’s efforts to get rid of so many belongings have been part of a plan she was sharing with no one?

“It was obvious to me she was troubled,” said Barbara Venezia, a community activist who knew Debbie through their work on various charities, responding to a query from Orange Coast. “Even with all she had, there was an underlying unhappiness that was evident. In the weeks and months prior to her death, she was so desperate it was impossible to be in her company.”

The summer of 2009, Debbie’s last, was an emotional roller coaster. On the upside, Debbie told friends that Robert Mills Jr., a sales and marketing executive who’d been seeing her for about two years, proposed. Mills, her second relationship of any length since the split with Arnie, was handsome and trim, his silver hair always perfect, and he opened doors and pulled out chairs for her. Debbie seemed proud to have him by her side. Mills declined to comment for this story, so it’s not clear exactly when, or if, he proposed.

But Debbie told friends she turned him down, or at least put him off. Perhaps she thought Mills’ timing was bad, or perhaps she was under too much stress to consider marriage. Maybe she still struggled with her feelings for Arnie. She had often told close friends: “Arnie is the only man I ever truly loved.”

Also in June, she won a small victory in the divorce case. Superior Court Judge Kim R. Hubbard sentenced Arnie to 40 days in jail—five days for every month he’d failed to meet his spousal support obligation. Arnie claimed that proceeds from the sale of a boat and his fleet of 11 collectible luxury cars were intended to make up for his nonpayment of support, but the court didn’t buy it.

That same month, the bruising divorce battle appeared to be grinding to a resolution when Judge Denner apparently reached a tentative decision on June 24, though he did not file that decision with the court clerk. Debbie had been seeking permanent alimony, which Arnie opposed. It’s impossible to say how it concluded, though, because Denner died before filing his final decision. The tentative decision was never made public.

But something else happened that June, a sentencing report submitted on behalf of Arnie in the contempt matter. Filed June 22, it included excerpts from a letter son Scott wrote in January 2006—before his drug overdose—in which he recounted an episode when his mother had been drinking. Addressing his father, Scott wrote: “Right now I feel motherless and I feel really sad seeing my mom do this to herself. I don’t want her to be killing herself and I don’t want to watch her do what I was doing.”

Two months later came another blow to the increasingly fragile Debbie. The day before Arnie was scheduled to begin his 40-day sentence, an appeals court in Santa Ana granted his request for a stay. On Aug. 20, the court vacated Arnie’s sentence, finding that Judge Hubbard had not followed procedure in imposing it.

Three weeks later, Mills found Debbie’s body in her mansion’s foyer. He’d left the house the morning of Sept. 10, friends say, and made the grim discovery when he returned that afternoon.

Details of the investigation were not forthcoming at first. Her obituary appeared in the local newspapers and on websites, with no mention of the circumstances surrounding her death. The Newport Beach Police Department offered little information, fueling speculation of foul play, a cover-up, payoffs—even murder.

But the Orange County coroner found no evidence of homicide. The 10-page report describes the victim as a woman in perfect health, 67 inches tall, weighing 138 pounds. Debbie was found in a simple cotton nightgown, wearing no ring. Her body bore no marks of a struggle, no evidence that she’d recently ingested drugs or alcohol. Based on medical and pharmacy records to which the coroner has access, the examiner concluded she was clinically depressed. Cause of death: ligature hanging.

A second autopsy was performed at the request of Debbie’s family by doctors at Hoag Memorial Hospital Presbyterian, toward which Debbie directed much of her fundraising energy. According to Puleo, those results were not significantly different.

In the end, Debbie Simon, the woman who seemed to have everything, apparently lost the one thing she needed most—hope.


Arnold Simon, 64, is living on the East Coast and is CEO of Aris Industries, an apparel licensee in which he bought a majority share in 1999. He sold the mansion on Harbor Island, closing escrow in June at a reported sale price of $27 million. He is in the process of settling Debbie’s estate with stepdaughter Lauren, and sons David and Scott.

Lauren Stone, 29, Debbie’s daughter from her first marriage, announced her engagement just weeks before her mother’s death. After postponing their wedding, she and her fiancé are to exchange vows this month in New Jersey.

David Simon, 25, has joined a religious order of the Catholic faith, vowing poverty, celibacy, and devotion to God.

Scott Simon, 20, attends Passaic County Elks CP High School, a special-needs facility in Clifton, N.J., and is making progress.

Robert Mills Jr. delivered Debbie’s eulogy at a memorial service at Mariners Church in Irvine. He lives in Newport Beach.

In Memoriam

In memory of her mother, Debbie Simon’s daughter, Lauren Stone, will host the inaugural “Touched by an Angel, Sisterhood of Survivors Spa Retreat” at Miraval resort near Tucson, Ariz., from Feb. 17 through 20. The retreat is designed to help heal those affected by suicide, and will include an appearance by singer Judy Collins. For details, e-mail
This article originally appeared in the October 2010 issue.

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