Tuesday, September 18, 2018

Raising the Flaggs Over Massachusetts

No American pedigree could be higher than to have an ancestor who was a “Minuteman” involved at Lexington, Massachusetts, the first battle of the American Revolution.  That was the banner carried by the Flagg family whose credentials included their name on a Boston liquor house for some seventy years — and beyond.

The story began with Josiah Flagg, a Worcester, Massachusetts, jeweler, engraver, and singing master, a man credited with forming the first colonial band and providing Colonial audiences with classical music.  Josiah also was a patriot, a member of the secretive “Sons of Liberty” whose goal was to win independence from England.  That pursuit found him firing at redcoats on April 19, 1775.  During the ensuing war Josiah was raised to sergeant in George Washington’s army.

Josiah’s son was a Worcester minister whose son, Barnabas “Barney” Flagg seemed to have strayed from the path of righteousness and in 1813, at the age of 21, landed in the Worcester jail, shown here.  Barney was accused of stealing $200.  Likely as a result of family influence he was released in May of that year.  Later Barney would marry and raise a family of whom the second-born in 1816 was Dennis F. Flagg, the whiskey man of this post.

This Flagg, born Francis Dennis, chose early in life to reverse his given names, and to honor his family’s military heritage by joining The Ancient and Honorable Artillery Company of Massachusetts.  Founded in 1638 and the oldest chartered military organization in North America, the unit would become an important part of his life.  The Artillery Company insignia is shown here. 

According to Flagg records, Dennis founded his liquor business in 1836 in Boston.  During approximately the same period he married his first cousin, Nancy Flagg, also a descendant of the famed Josiah.  They would raise a family of seven children, including three sons — Frederick D., Charles P., and Henry D. — all of whom would be involved in the Flagg liquor and wine business.

Flagg selected his location well at 165 Blackstone Street.  The avenue had been opened only shortly before on a landfill completed in 1833.  The name was an official tribute to the Reverend William Blaxton, a missionary to the Shamut Indians and considered the first non-native inhabitant of the area.  With other landfills following and development of the Town Dock for the nearby Quincy Markets, this section of Central Boston became increasingly retail and market oriented.  As new four and six story brick buildings were built, Flagg occupied one of them at ground level, taking advantage of the growing crowds jostling each other on market day, as shown here.

Flagg’s front window was a showpiece of the neighborhood, changed regularly to reflect the season of the year and holidays.  A trade publication, Liquor Store & Dispenser, noted and photographed the singularity of one of Flagg’s Spring display, shown above, featuring bottles of rum.

  Flagg’s Blackstone window also frequently featured hisflagship brand “Kentucky Bourbon,” sold in amber glass bottles with an elegant label from D. F. Flagg & Co.  The label featured an elaborate monogram and indicated that the proprietor also dealt in wines and teas.  

By the 1860s Flagg was financially able to move his family into a newly constructed home, shown here, in fashionable Union Park on Boston’s south side.  Considered today to be the largest urban Victorian neighborhood in the country, Union Park houses were built circa 1860 and gave the area a distinctly English look.  As soon his sons reached their mid-teens Dennis Flagg brought them into his firm and taught them the business.  The 1870 census found Fred, 25, in management and Henry, 16, and Charles, 15, working as clerks.

By this time Flagg had expanded to a second enterprise, a grocery store located at 150 Cambridge St. operated as “Flagg & Favor” with a partner, E. W. Favor.  In time Dennis Flagg’s health seemingly declined.  By 1880 he was no longer involved in the grocery or the liquor house that bore his name.   His three sons, with an older partner, George Hart, were operating Dennis F. Flagg & Company.  In October 1884 Flagg died at the age of 68 and was buried in Forest Hills Cemetery, Jamaica Plains, Suffolk County.  

With her husband’s death, his widow, Nancy, sought a change of scene.  Two months after his interment, she purchased land from the State of Massachusetts and commissioned a new house at 206 Commonwealth Avenue.  Designed by Allen and Kenway, noted Boston architects, the Flagg home was completed in July 1886.  Two of Nancy’s children lived with her: Henry Flagg and Elizabeth (Flagg) Simmons, a widow.  They all previously had resided at  the Flagg home in Union Park.  Nancy had only a few months to enjoy the new home, however,  dying in November 1887.

After Frederick Flagg died in 1891 at the age of 47, management changes occurred at the liquor house.  Now Charles was listed as proprietor, along with Hart.  Charles and Henry also owned a real estate firm that operated from the 185 Blackstone address with Henry taking the lead in that enterprise.  Charles sponsored a large ad in a local business directory citing 1836 as the year his father founded D. F. Flagg & Company at 165 Blackstone Street and noting 69 years of continuous operation.  Although his date of death is unknown, Charles Flagg disappeared from Boston directories after 1909.  About that time, the company name and liquor stock appear to have been sold.  By 1913 D. F. Flagg & Company was recorded as operated by Harry B. Golden.

Although shut down by National Prohibition, the company name was revived after  Repeal.  A 1948 directory listing indicates that with T. H. Hagan as manager, the Flagg firm was featuring the “finest in imported and domestic liquors” and located at 206 Dartmouth Street, Boston.  A 1954 listing shows Harry Nathanson as manager.  A 1960 directory recorded D. F. Flagg & Co. still in the liquor and wines  business at the Dartmouth address.  

Accepting 1836 as the year Dennis Flagg founded his establishment on Blackstone Street, the run of some seventy years under family ownership is certainly a record for Boston liquor houses.  Moreover, the fact that despite National Prohibition, the Great Depression and World War Il, the name D. F. Flagg survived in Boston’s liquor trade for at least 125 years is reason enough to celebrate the Flaggs, a family born with the Revolution and a multi-generational American success story.

Note:  The story of the Flagg family was brought to my attention by Peter Samuelson, a New England collector of labeled whiskeys who frequently asks my thoughts on pre-Prohibition brands.  After he sent me the two photos of Flagg bourbon shown here, I was spurred to undertake the research that resulted in this post.  Thanks, Peter, for providing the photos — and my incentive.  


  1. I have been searching for some 30 years for the parentage of Barney Flagg, the black sheep of the family. You have revived my hope. Could you let me know your source for saying that he was the grandson of Josiah Flagg? Thanks in advance

  2. Joseph: My information came through a DAR application/statement on Mrs. Elizabeth Flagg Simmons that links her father, Dennis F. back to Josiah. It item does not mention Barney --but he is listed as the father of Dennis -- specifically but it may be because of his problems. I just clipped the reference off the internet and did not take a full reference. Sorry.