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More Than Maymont: "The Dooleys of Richmond" Explores the City’s Most Important Unknown Family

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"I was always a ‘bull’ on Richmond. The first money I ever made invested, as they say out west, ‘in Richmond dirt.’ I have been investing in it ever since, and I have never had cause to repent my judgment.”

While the speaker was addressing the Richmond Chamber of Commerce, it wasn’t the same audience that rallied this month at the Omni hotel downtown to mark the 150th anniversary of the regional business group — although it could hardly have found a more articulate, informed or more prosperous keynote speaker. These words were delivered in 1890 to the Richmond chamber by James Henry Dooley (1840-1922), a Richmonder whose name might not be known to many, but whose benevolence touches virtually every resident and thousands of visitors.

Jim Dooley, as he was called by family and associates, and his Lunenburg County-born spouse, Sallie May Dooley, have a legacy that includes the original Richmond Public Library on East Franklin Street, the Children’s Hospital, St. Joseph’s Villa on Parham Road, plus the region’s beloved cultural and horticultural pièce de rèsistance, Maymont. After living modestly for many years on Grace Street in a house that they shared with a number of other couples — and then later on Franklin Street, the two moved in 1893 to their glorious 100-acre estate in the West End and continued to adorn it with exotic gardens, specimen trees and architectural follies throughout the rest of their lives.

So we know their generous legacy, but do we know the Dooleys? How did they meet? From whence came their wealth? What informed their philanthropy?

“The Three Graces” a reproduction of an Antonio Canova  sculpture, and limestone Romanesque-style columns are shaded by a magnolia tree near the Maymont house.
  • “The Three Graces” a reproduction of an Antonio Canova sculpture, and limestone Romanesque-style columns are shaded by a magnolia tree near the Maymont house.

For thoughtful and often surprising answers to these and other questions, Mary Lynn Bayliss, a Richmond historian, has written a tight and spare — 222 pages — but well-researched and deeply informative work, “The Dooleys of Richmond: an Irish Immigrant Family in the Old and New South” (University of Virginia Press).

She thoughtfully and even-handedly traces the story of two generations of Dooleys in Richmond who were active in the years leading up to, during and following the harrowing Civil War.

Currently, with our national discussions of religion, race, gender and economics turning touchy, defensive and often apologetic, Bayliss doesn’t flinch at placing the Dooleys squarely in their own time and social class. When various Dooley men folk go off to serve the Confederacy, enslaved manservants accompany them to the front. During Reconstruction, at Democratic political meetings when the Southern anthem “Dixie” closes the proceedings, Jim Dooley joins in — well, who of Irish descent doesn’t like to sing? And as to woman’s suffrage, let’s just say that worthy cause didn’t get Sallie May Dooley’s endorsement. Later, when she buried her Catholic husband, he got a Protestant funeral conducted by her Episcopal pastor.

Bayliss delivers her history with refreshing dispassion.

Mostly, however, this is a story of antebellum and Gilded Age wealth-making by two men in the Upper South — and it’s no Horatio Alger yarn. John Dooley, Jim’s father, immigrated in 1834 to the United States from Limerick, Ireland with a number of immediate family members. Two years later he married Irish-born Sarah McNamara, and they moved to Richmond. Here they settled on East Broad Street just two blocks from the Capitol, and it put them in the center of the city’s political and social whirl. St. Peter’s Catholic Church, which was then the cathedral of the Diocese of Richmond, was also within walking distance.

John Dooley possessed the ability to make hats, an entrepreneurial spirit, and fair and level judgment. Not unimportantly he had enough capital to launch a retail-and-manufacturing operation. He would also invest in at least five railways — travel technology the launch of which coincided with his arrival. By 1861 he and his family were prosperous manufacturers and retailers that were supportive of their church and community. But here’s a surprise: John was also seriously vested in Chicago real estate, reaping the benefits of the suburban residential expansion in that growing metropolis. So he ran parallel but quite different operations — making the Midwest a place where he settled and supported other relatives seeking refuge from the Emerald Isle.

When war came he followed his adopted state and served in the Confederate army, achieving the rank of major. His perhaps greater service came after he resigned due to poor health: He was brilliant at organizing an ambulance committee and other relief operations as Richmond absorbed ever-growing numbers of wounded and dead.

His son, Jim, who was at Georgetown University when war broke out, returned home to read law and manage the family hat business. But he, too, enlisted and soon had his right wrist shattered by gunfire near Williamsburg. He became a prisoner of war.

Much of Richmond, the Dooley business included, was decimated in 1865, but John quickly reopened a limited version of the hat operation. Jim followed a path directly into law, quickly making a name for himself by taking on underdog clients. He also became a leader in politics, representing Richmond in the legislature. But it was the opportunity provided by rebuilding the railroad and canal infrastructure of Richmond and the South that kept Dooley-the-younger focused. This led to major investments in St. Paul, Minnesota — and markets as far west as Seattle, Washington.

Jim had seen how his father operated his business on a national scale. And he had seen how his father supported family, members of his faith and local community causes.

Author Bayliss, battling the fact that the Dooleys had their personal correspondence destroyed — a historian’s nightmare — has written a smooth, rich narrative using other sources, especially newspapers, and she puts special emphasis on the surprisingly national scope of James Dooley’s railroad operations and other investments.

When asked, a friend who recently read “The Dooleys of Richmond” told me that his take-away was this: “They looked after their family and they looked after Richmond.”

Indeed they did. And thanks to Mary Lynn Bayliss, it is an inspiring story. S

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