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Duncan vs. Flynn- A Story of Mid-20th Century Housing Discrimination

Updated: Dec 2, 2022

During the years that followed the second world war, many white Americans experienced unprecedented prosperity in large part due to programs like the GI Bill that enabled them to more easily purchase homes than ever before. Unfortunately, their fellow black citizens were frequently denied these same opportunities. Massachusetts Commission Against Discrimination (MCAD) was a state body created in 1945 to enforce state-level anti-discrimination laws, its 1965 Annual Report indicated that several Longmeadow citizens both participated in and fought against this disgraceful practice.

In February of 1965, David Duncan III, a 40-year-old African American WWII combat veteran and manufacturing engineer at Pratt and Whitney, was looking to purchase a home when he came across a listing in a local newspaper for 24 Pine Hill Road in Springfield. Mrs. Duncan called the listing agent, Robert J Flynn, who was operating his real estate business, the Robert J. Flynn Real Estate Agency, out of his house in Longmeadow. During the phone conversation, Flynn informed Mrs. Duncan that the house was for sale for a price of $21,500 (about $190,000 in October 2021 dollars) and they agreed to meet on February 6th so the couple could see the house. After touring the house, Flynn informed the Duncans that the price of the house was $25,000 (about $221,000 in October 2021 dollars). When Mr. Duncan protested that the real estate broker had told his wife over the phone only a few days earlier that the price was only $21,500, Flynn retorted that his wife must have misheard him.

A little more than a week after the showing with the Duncans, Mr. Flynn received a call from Elizabeth Grandison, a white woman, also asking to see the house for sale. Unbeknownst to Flynn, David Duncan III had contacted MCAD to file a complaint about his experience trying to purchase 24 Pine Hill Road and the Commission had sent Mrs. Grandison to “test” Duncan’s claims. Ms. Grandison was a member of the Springfield Urban League and a civil rights activist from Longmeadow. She inquired about seeing the house and Mr. Flynn offered to show it to her that day. After touring the house, Flynn informed Mrs. Grandison that the house was priced at $21,500 but he would be willing to accept an offer as low as $20,000 (about $177,000 in October 2021 dollars).

After the showing, Mrs. Grandison reported back to MCAD and informed them of the results of the showing and confirmed the charge of discrimination. Based on Grandison’s and the Duncans’ testimony, MCAD Commissioner and Longmeadow resident John F. Albano, filed an injunction against Flynn in Hampden County Superior Court in order to prevent Flynn from selling the house to anyone except Duncan. Albano had been appointed to the commission in 1964 and concurrently served as president of the Springfield-Chicopee-Westfield AFL-CIO. Albano brought his nearly 30 years of experience fighting against unfair labor practices and used it to fight against racial discrimination.

In court, Flynn’s attorneys along with those of the property owner Jean C. Tierney argued that they should be permitted to sell the house because Mr. Duncan was misrepresenting the facts. They asserted that they had an asking price of $25,000 and were only willing to go as low as $21,500 and that the Duncans had told Flynn that the highest they were willing to pay was $20,000. The Duncans reiterated their story of the phone pricing vs. the in-person pricing. Judge Francis L. Lappin attempted to mediate and try to have the two parties come to an agreement. However, when it was apparent that the defendants were not going to come down in price low enough for the Duncans, he dismissed the injunction request allowing Tierney and Flynn to go about their business of selling the home.

While MCAD had failed to force the house in question to be sold to the Duncans, the commission still needed to have a public hearing to assess if discrimination had taken place. On September 20, 1965, with the benefit of both Duncan and Grandison’s testimony the MCAD commissioners Malcolm C. Webber, Ben G. Shapiro, and Ruth M Batson found Robert Flynn guilty of housing discrimination. MCAD subsequently ordered Mr. Flynn to stop discriminating against anyone he interacted with as part of his real estate business, he must include in all of his newspaper advertisements for his real estate business that they were “Equal Rights” listings and he was required to report in writing the steps he had taken to comply with the order to MCAD.

After the ruling, in October of 1965, Flynn sued MCAD to obtain a restraining order to prevent the ruling from going into effect. In February of 1966, Judge Joseph Ford ruled that Flynn needed to comply with the order. As a result, Flynn placed the ads like the one pictured.

In April of 1965, Elizabeth Grandison and her husband sold their house in Longmeadow and moved to Boston.

As for Mr. Duncan, in the years following the decision, he did successfully purchase a home in Springfield, MA where he lived until he passed away at the age of 80 in 2005. Duncan found much success and was a fixture in the Springfield community in the 40 years following the decision. He received numerous awards including the “Eyes on the Prize'' award in 1996 from WGBY and induction into the Black and Gold Society of his alma mater the Wentworth Institute of Technology. He was a member of the VFW, was very active in the Freemasons serving in numerous roles over the years, treasurer of the Alden Street Baptist Church, and on the Board of Directors of both the Dunbar Community Center and the Springfield Girls Club Family Center. Perhaps most notably, Duncan served as the first African American on the Springfield Police Commission and served as Chairman during the period of civil unrest following the assassination of Dr. Martin Luther King, Jr.

Albano continued to serve as an MCAD commissioner until 1969. After the end of his time on MCAD, he continued to play a large role in the labor movement in Western Massachusetts. In Longmeadow, he spent many years serving the Jewish Home for the Aged. When he died in 1979, his funeral had over 500 mourners in attendance and included political and labor leaders from across the state.

Mr. Flynn continued to operate his real estate business in Longmeadow after the MCAD decision until his death in 1969. Flynn never gave a reason for discriminating against Mr. Duncan, specifically declining to comment to the press after MCAD’s decision. The behavior that Flynn and others like him displayed created a system that denied black people the ability to equitably purchase a house.

This practice affected black homebuyers in the mid-20th century and this lost economic opportunity was passed on to their children and their children’s children. For example, if Mr. Duncan had been able to purchase this house at a price of $20,000 and then sold it today for Zillow’s current estimated value of $254,000, he would have made an inflation-adjusted profit of about $77,000 which he could then pass on to his children and/or grandchildren. In 1968, Congress passed the Fair Housing Act (FHA) which enshrined equal housing opportunity at the federal level and provided federal enforcement mechanisms to combat housing discrimination which were much more of a deterrent than most state anti-discrimination laws. While the work that David Duncan III, John Albano and Elizabeth Grandison combined with the passage of federal legislation, certainly has improved the housing discrimination situation, inequities and discrimination are still very much a problem all over this country and even in our region. That is why, if you are living in Massachusetts and feel you have been a victim of discrimination, you can contact MCAD either by phone at (413) 739-2145 or by email at and if you are living anywhere in the USA and you feel you have been the victim of housing discrimination, please contact the Department of Housing and Urban Development either by phone at (800) CALL-FHA (800-225-5342) or by email at

Special thanks to the Hampden County Clerk of Courts staff for their assistance with this research.


  • America, United States of. “CPI Inflation Calculator.” U.S. Bureau of Labor Statistics. U.S. Bureau of Labor Statistics, 2021. An Exceptional Opportunity, Robert J. Flynn Agency.

  • An Exceptional Opportunity Springfield Union, March 13, 1966.

  • Assessors, Springfield. 24 Pine Hill Road. Photograph. Springfield Assessors Database. Springfield, MA: Springfield Assessors, April 29, 2016. Duncan, Tracy.

  • Mr David Anderson Duncan III, 80 The Republican. July 28, 2005.

  • Flynn, William. Robert J. Flynn, Realtor, Dies Springfield Union News, July 25, 1969. Hampden County, Massachusetts Deed Book 3105: 128

  • Springfield, and Malcolm Webber, ANNUAL REPORT of the Massachusetts Commission Against Discrimination January 1, 1965 to December 31, 1965 § (1966).

  • Springfield Union, The (Massachusetts) 25 February 1965, Flynn Is Cleared,

  • Springfield Union, The (Massachusetts) 3 March 1966, Realtor is Told to Comply with MCAD Order,

  • Springfield Union, The (Massachusetts) 18 November 1966, Virginia Meyers Marries Lt. Wilfred Grandison,

  • Sunday Republican, The (Massachusetts) 11 November 1979, John Albano Hailed as a Friend in Need,

  • Zillow, Inc. 24 Pine Hill Rd, Springfield, MA 01118.” Zillow, 2007.

Contributed by Tim Casey, LHS Board Member

Originally published February 3, 2022

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