Gregg Sherwood (Her given first name was Dora Mae.) worked mostly as a scantily clad pin-up model and landed a handful small roles in forgettable film in the early 1950s. She married Walter Sherwood, a New York Yankees ticket manager, was eventually indicted on charges of grand larceny. According to Sherwood, most of the $43,000 he took went to Gregg’s parents. Sherwood divorced her in 1949. But in 1953, she hit the jackpot by marrying Horace Dodge Jr. the son of Horace Elgin Dodge, Sr., of Dodge Brothers Motor Company and Anna Thompson, of Dundee, Scotland. Horace Sr. died in 1920 leaving Anna with two small children and a massive car manufacturing fortune.
Horace Dodge Jr.
Gregg Sherwood was 28 he when she married the 51-year-old. Dodge, power-boat racing playboy had already had four wives. (Her number of husbands is a matter of debate; some sources say four; others cite five.) Their courtship was a rocky one, to say the least. At one point, he accused her of stealing four of his solid gold cigarette lighter, prompting police to pick her up in a Detroit bus station but they patched things up and were married at his mother's Palm Beach mansion, Playa Riente, (“Laughing Beach”) magnificent 70-room showplace set on 27 ocean-to-lake acres. The main house featured 15 master bedrooms and a bachelor’s wing permitting single male guests to come and go without being announced.
Three weeks after Anna Dodge bought Playa Reinte, she married her real estate agent, Hugh Dillman who was fourteen years her junior. Dillman had arranged a tour for a group of young African-American singers throughout Europe. It was on that tour that he met the middle-aged Anna Thompson Dodge, reportedly the richest woman in the world at that time.
The house he found, Playa Riente had belonged to Joshua Cosden, a wealthy Oklahoma oilman who had lost his fortune in horse racing. (Cosden regrouped, borrowed money and invested in the exploration and drilling of the West Texas oil fields, accumulating another fortune estimated at $15 million which he lost in the great depression) Dillman and Dodge were married May 8, 1926, in her Michigan mansion.
Anna Dodge, Horace’s mother, stayed in Palm Beach after her divorce and in the mid-1950s tried to turn her estate into a school or club, but the Palm Beach City Council refused to approve the zoning change. She sued and lost in court. She held a large estate sale and then had the mansion demolished in 1958. Anna returned to her Michigan estate Rose Terrace in Grosse Pointe Farms. (She had yet another tremendous estate, St Leonard's at Clewer, near Windsor, in Berkshire, in England. Anna died at the age of 103 in 1971.
Horace and Gregg led an extravagant life with Gregg spending her husband’s money lavishly. New York diamond czar Harry Winston sued, charging the couple had failed to pay off $176,800 in jewelry, including an $82,000 diamond ring. Mrs. Dodge returned most of the jewelry. Dodge insisted his wife bought much of the merchandise without his authorization.
In February 1954, a month before their son John was born, the first suit was filed against Dodge by a Palm Beach jeweler for allegedly failing to pay $524.00 Two months later, the Nat Lewis Corp. of New York sued Dodge for a bit more: $125,000 in unpaid purchases. (Which included a charge for two gold baby diaper pins, $179 each; several pieces of baby furniture, $2,325; an electric train, $1,700; a diamond ring, $6,300, and a diamond bracelet, $11,750.)
Dillman and Dodge
By 1958 the Dodges apparently were so mired in debt that his mother, Anna Thompson Dodge, foreclosed on their Palm Beach home to keep it out of the hands of creditors. That suit was the 32nd against her son since the beginning of 1954. The bills she had run up in 1961 included $21,500 for a platinum ring, $8,000 for gold dishes, $6,209 for clothes and $3,500 for a grand piano. An attorney for Dodge' contended her annual spending might exceed $300,000…in 1960 dollars. Dodge said that his income was less than $200,000 and that since 1959 he had borrowed more than $1.5 million from his mother.
In 1961, Dodge had enough of Gregg and started divorce proceedings against her, telling the press ""She's a spendthrift. I can't afford her. I can't afford the woman". However, in all fairness, Dodge had a very serious drinking problem. Horace died before the divorce was finalized and Gregg, whom Horace had purposely left out of his will, inherited an estate saddled with claims of $12.3 million and assets of only $718,000.
Shortly afterward Gregg sued her mother-in-law for $10 million, contending she had interfered in the marriage and turned Horace against her. Gregg also claimed she had another million coming based on the prenuptial agreement. The mother-in-law had always held the family purse strings as trustee for the $57 million estate left by her late husband, and she didn't let go after her son's death. In April 1964, Gregg and Anna Dodge, then 93, reached an out-of-court settlement, never unveiled but apparently to be paid in installments. Gregg's attorney said it totaled about $9 million; the lawyer for the senior Mrs. Dodge said it was considerably less.
As a single woman again, Gregg had a short-lived fling with Dean Martin. Although she downplayed it and another with baseball great Joe DiMaggio, making the scandal sheets for her midnight run-in with DiMaggio at an LA hotel where she was said to be pounding on DiMaggio’s door while she was almost too drunk to stand. Gregg always said it never happened. However, she managed to make the pages of the notorious scandal magazine, Confidential when she landed in the hospital after a bar fight with a flamenco dancer.
In 1965, she married Dan Moran, an Irish born former New York City beat cop whom she had hired as a bodyguard. She was 45, he was 27. The two of them blew their way through $11 million on parties and private jets. A judge later found that they managed to spend $34,000 a week (roughly $90 thousand today) In the late 1960s, the Moran’s bought their estate at 1089 S. Ocean Blvd. in Palm Beach. They remodeled the house, installing an extensive security system that included six TV cameras sweeping the 450 feet of sand bordering the Atlantic. Helping to fortify their home was a pack of Vizla dogs, a breed of Hungarian pointers. The dogs led to at least four suits, the largest ending in a $10,000 award to an upholsterer who alleged she was bitten. The family settled similar claims out of court. Meanwhile, Gregg's free-spending lifestyle spawned suits for allegedly failing to pay the debt.
Facing financial ruin and jail time for his messy financial dealings, Moran shot himself to death in 1978. According to Gregg, Moran had threatened to shoot her and her son John “He just felt we should all quit He was angry at me because I wouldn't agree to shoot myself and go with him,"
Gregg said that she woke up that morning at about 7 am. She slept in a different bedroom because Moran’s drinking kept him up all night. She said she entered his bedroom and pulled a chair close to the bed and said. "You said you wanted to have a serious talk today. I think we'd better talk, too. When he sat up I could see he was not himself in any way. Besides being very drunk, he was crazed His eyes were bulging and red”
Moran said he didn’t want to talk and walked to a nearby closet and came out charging after Gregg screaming that he would kill her and her son as soon as he arrived home. He also promised to shoot the couple’s four dogs. "He said there was nothing more for us to live for. I knew something was wrong."
When Moran headed for the spot where he kept a gun, Gregg ran out of the room and then heard a gunshot "At first I didn't know if I'd been hit or what." She said that she spun around to see Moran fall back from a sitting position on the bed, blood gushing from his chest "I didn't know what to do," she said. "I don't know what I did for a while."
The life insurance policy for $1.2 million on Moran had lapsed prior to the shooting because of nonpayment of the premiums.
That same year, 1978, Gregg filed for bankruptcy after amassing $3.5 million in debt and then in 1979, she was arrested for grand larceny after misappropriating $434,000 from her son John’s $8 million trust fund and another $75,000 fraudulently obtained from a New York bank. (It was John who posted her bail)
In her later years as Palm Beach matron, she dabbled in publishing, producing a short-lived society tabloid that was ultimately unsuccessful, in spite of her edgy observations. Gregg Dodge died on May 27, 2011, at the age of 87.