HARWICH, Mass. – Anne Flaherty was a beautiful blond who had earned a certain notoriety after serving six years in prison for running a prostitution ring on Cape Cod.
Ken Simon was a successful financial manager who retired early here after amassing a small fortune.
Their marriage – the third for both – caused something of a stir in this quaint waterfront village on Nantucket Sound, but that was nothing compared to the shock waves it sent through Simon’s family.
His three adult sons did not attend the July 2004 wedding. A year later, they filed a series of lawsuits against Anne Simon, 44, saying liver disease and alcoholism had left him mentally incompetent and that she plotted to kill him.
They asked a judge to end the marriage – either through annulment or divorce – and to stop her from spending any more of his money.
Ken Simon’s death last month at age 72 did little to ease the hostilities. As his will makes its way through the courts, his sons are continuing what their lawyer describes as an effort to keep her from squandering his fortune, estimated at $5 million to $9 million.
“I think what the boys want is for this woman not to profit by what they see as fraud on their father and a scheme developed by her to take his money under the guise of being his wife,” said Russell Wilkins, an attorney for Simon’s sons, Kenneth Jr., Christopher and Kurt. “In fact, she was no more his wife than some other person on the street.”
Anne Simon, 44, calls her sons-in-law “gold diggers,” and says they are trying to get back at her for embarrassing the family with her past as a prostitute.
“They’ve never met me. Who the hell are they to judge me?” she said. “It’s a witch hunt because I was a madam.”
Anne Flaherty met Ken Simon in 1992, when she was running a disc jockey and karaoke business on the South Shore and Cape Cod. Simon, whom she described as “the silver fox-type,” was 27 years older. He pursued her from the moment they met, she said, but insists the relationship remained platonic for a decade.
By 1995, Flaherty’s second marriage was falling apart. She told television and newspaper reporters that her then-husband tried to strangle her with a nylon stocking. He was sentenced to six months in prison for violating a restraining order to stay away from her.
A few months after that, Flaherty was arrested in Bourne when she answered a call from an undercover police officer looking for “Kazuma the Tiger Woman.” Investigators said that was one of the names advertised by the escort service she ran, which employed at least six prostitutes.
“My family disowned me when I was arrested,” she recalled, saying Ken Simon was the only person who stood by her.
He visited her regularly in prison, proposing on the first visit.
“He was nonjudgmental,” she said. “He had a chivalrous side.”
“I realized the answer to my prayers was standing right in front of me,” she said. “I fell in love.”
They were married about a year after she was released from prison, in the backyard of Simon’s waterfront home, in a gazebo he bought to fulfill his bride’s childhood dream of her wedding day.
But the romance did not go over well with the sons from Simon’s first marriage. All three skipped the wedding.
“It never occurred to me to marry the guy for his money,” said Simon. “Anyone who knew Ken and I knew we were deeply in love.”
They spent the next year traveling around the world, until Ken Simon’s illness forced them to return home.
In August, a temporary guardian was appointed at the request of his sons after a judge found him mentally incompetent. The guardian then filed a lawsuit against Anne Simon, alleging she spent at least $195,000 in the year they’d been married.
A judge froze the couple’s assets and immediately halted renovations to the Harwich Port house. Anne Simon said she was trying to make the home handicapped-accessible for her husband, but the sons claim in court papers that she was planning to spend $200,000 to $300,000 on a home office for herself, a new master bedroom, new floors and a two-car garage.
Ken Simon died Nov. 2 from advanced liver disease caused by alcoholism. Separate memorial services were held, one by his wife, the other by his children.
Before he died, he deeded the house – worth an estimated $1.6 million to $1.8 million – to himself and his wife in a legal arrangement that would allow her to own it outright after he died. If a court grants the annulment, Anne Simon will no longer be entitled to the house.
In his will, he left her $100,000, plus another $110,000 in a trust to be used only for her education, said Gerald Nissenbaum, an attorney for Simon’s sons.
“Anne Simon thinks she’s going to live in style for the rest of her life by virtue of her marrying the guy,” he said. “That is just not in the cards.”
Through their lawyers, Simon’s sons declined to be interviewed.
In their annulment petition, they claim she married their father for his money and plotted to kill him either by giving him an overdose of prescription medications or pushing him down the stairs while he was drunk.
“Before the marriage, defendant stated to others she did not love plaintiff but was going to marry plaintiff so that, thereafter, she would then kill him to get all his money,” the complaint states.
Nissenbaum said he has two witnesses who can verify those claims. He would not identify them, but media reports have said one was a woman with whom Anne Simon had a lesbian affair in prison.
She denies the claim, saying she was “deeply in love” with Simon and that the former inmate is “a scorned woman” trying to get back at her.
“I never conspired or talked about killing anybody,” she said.
The will is being handled in Texas, where Simon maintained his legal residence. Kenneth Simon Jr. is executor of the estate.
Anne Simon says the legal actions by Simon’s sons have left her “destitute” and barely able to pay for food. But Nissenbaum says she “feathered her nest” before her husband’s death, prepaying the rent on an apartment in Somerville and the monthly payments on her car.
A Christmas card photo from 2003, before the Simons were married, depicts happier times.
The smiling couple is sitting at a table, holding hands. “Season’s Greetings. From Our Home to Yours,” the card reads.
Even Anne Simon’s enemies acknowledge they were in love.
“He thought she was beautiful,” Nissenbaum said. “He wanted to marry her and he wanted to travel with her. But I think his competency was compromised at that time.”
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