Lillian Loomis Dempsey: 

The Heiress of Northoline

A color postcard from around 1910 depicts “Northoline,” the then-new West Lane mansion of Lillian Loomis Dempsey. Recently widowed, Mrs. Dempsey had built the house after receiving a huge and somewhat controversial inheritance that made headlines from Georgia to New York.

 Lillian Dempsey was the wife of Thomas C. Dempsey, who had  died July 4, 1899, in Asbury Park, N.J. A few months later, on Sept. 25, 1899, The Baltimore Sun reported that “active negotiations have been pending for several weeks to prevent a threatened controversy” over Thomas Dempsey’s estate. 

That estate, according to The Sun and other newspapers, was said to be worth $1 million — equal to about $30 million in today’s currency.

“While Mr. Dempsey, who was 85 years old, was in bed three days before his death, he executed his will, by the provisions of which the bulk of his fortune goes to his widow, Lillian Loomis Dempsey, whom it appointed executrix,” the Sun continued, then adding, “She is about 32 years old and had formerly been the companion of one of his daughters by his first wife.”

In his will, Thomas left nothing to that daughter, Nellie, who was married to Richard Needham, a wealthy merchant from Columbus, Ga. He also ignored his son, Wilson P. Dempsey, who was an “inmate of a sanitarium” near Baltimore, The Sun said.

“Mr. Dempsey was a retired dry goods merchant of a Southern family, having his residence in Macon, Ga. He owned valuable real estate in that city and an old homestead in Ireland. The rest of his estate is comprised of securities, the exact amount of which is not known.”

Dempsey had lived most of the year in New York City and elsewhere in the North. “He was a member of the Roman Catholic Church and made liberal gifts to charity,” The Sun said. “There was much astonishment when it was ascertained that he had made no charitable bequests.”

While the will had been offered for probate in Macon, no formal objection had yet been filed, the newspaper said, adding, however, that “Mrs. Needham is much dissatisfied with its provisions, as she thinks she is entitled to a share of her father’s fortune. She has threatened to make a contest in behalf of herself and her brother.”

Who were this wealthy 85-year-old man and his 32-year-old wife?

A native of Ireland (he was not from a “Southern family,” as the Sun suggested), Thomas Charles Dempsey had been born in 1814 and came to the United States as a young man. He became a citizen in 1842 in Savannah, and was soon living in Macon where he amassed his fortune as a retailer and investor in real estate. Around the beginning of the Civil War, he married Marie Lumpkin. Wilson was born in 1863 and Ann Ellen, called “Nellie,” was born in 1871. His wife died in 1885.

Lillian Loomis Wickes was born in 1867 in Macon. While in school there, she became friends with Nellie Dempsey. At some point the widowed Thomas Dempsey began noticing this companion of his daughter and by the early 1890s, he had proposed to her. They were married around 1893, when he was about 79 and she was 27.

One wonders how Nellie Dempsey felt, seeing her old schoolmate become her stepmother. 

The next year, Lillian and Thomas had a daughter, Marie Monica. In 1896, Thomas Charles Jr. arrived, and on June 6, 1899 — a month before his father’s death — Norbert Anthony was born.

According to subsequent newspaper accounts, including an article in The New York Times, Mrs. Dempsey hired a New York City lawyer named Robert O’Bryne to handle the dispute over the will. In the end, Nellie and her institutionalized brother got $250,000, leaving around $750,000 for the widow Dempsey. That today would be about $7.5 million for Nellie and Wilson, and  $22.5 million for Lillian.

Attorney O’Bryne claimed a lot of credit for the settlement, but it is quite possible that Lillian Dempsey felt an obligation to her old friend and his brother — her stepchildren — and that Nellie, hardly poverty-stricken, realized that she would never get much more than that, especially considering that her dad had fathered  three children with Lillian — all of them then under 10 years old.

As one dispute ended, another began. Attorney O’Boyle filed suit in a New York City court in July 1900, claiming he had not been paid for his services. He maintained “he was the one who kept down a contest over Mr. Dempsey’s will, and for his services he was entitled to $24,000,” The Macon Telegraph reported.  

It added, “The widow vigorously denied owing him any money. She said she had never employed him, but had paid him for all he had done. He is insisting that what he did was worth the $24,000 additional.”

That $24,000 would be about $731,000 today.

The case went to a referee who apparently worked things out without publicity.

Meanwhile, Lillian Dempsey, who had been living in New York City, decided she would like a country house and somehow came upon a tract of West Lane farmland on a small ridge overlooking South Salem. The land was owned by John Brophy, who, like her husband, was a native of Ireland. Brophy had for many years been a  U.S. customs official at the Port of New York, a job in which he dealt with many influential people. It’s possible he and Thomas Dempsey had known each other and that Brophy offered the land to his widow.

She bought the property in 1901 and built her 22-room house. It is not known how much  she used Northoline, but she probably was in New York City and Macon much of the year. She apparently lived a quiet life, and her name no longer appears in newspaper articles. She was not active in the social world nor did she seem to become involved in any philanthropy. She was living in Macon in 1930, but by 1940 when she was 73, she shared a home in Scituate, Mass., with her two sisters. She died in 1946 in Cambridge, Mass., and is buried in Macon.

Her house is at 209 West Lane, a little south of Silver Spring Road and a bit north of the New York line — presumably the inspiration for its name, though it’s really more west than north of the state line. It later had a less controversial but far more famous owner:  Metropolitan opera star Geraldine Farrar, who bought the place in 1924, renaming it “Fairhaven.” Here, though retired from the stage, she entertained many international celebrities in the arts, especially the world of music.

Now surrounded by trees and shrubs, the house still stands, though at last look, it was painted white.