From "The Clerks of the Four Horsemen" by Barry Cushman:
"Chester Gray, another James C. McReynolds short‐timer, clerked for the Supreme Court Justice for just one month during the 1925 Term. Gray was born in 1898 in Pittsburgh, where he attended public schools and Martin’s Business College.
He began his work life as an office boy for the Carnegie Steel Company, becoming proficient in shorthand by the age of sixteen. Following his service as a clerk in the Office of Naval Intelligence during World War I, ironically enough, he served for nearly two years as confidential secretary to then‐ assistant secretary of the Navy and a future McReynolds nemesis, Franklin D. Roosevelt.
He then worked as a secretary for the Treasury Department for almost two years and for the Department of Justice for one year. Gray attended the Emerson Institute in Washington and received his law degree in 1925 from the National University Law School, where the editors of the yearbook predicted that he would become “Dean of Northwestern University.”
He was admitted to the District of Columbia bar later that year. Gray’s tenure with McReynolds lasted only from February 25, 1926 - March 23, 1926. His departure before the conclusion of the 1925 Term suggests that the position with the Justice may not have been a good fit.
After leaving McReynolds, Gray married the former Ruth Hungerford of Wilkes‐Barre, Pennsylvania, and worked briefly in private practice before joining the Washington, D.C. Corporation Counsel’s office in 1928. He worked continuously in that office for the remainder of his career. By 1938 he had risen to the position of chief trial counsel, and in 1956 he became the District of Columbia’s chief legal officer.
He died of a coronary thrombosis at the age of sixty‐seven in 1965. He was a Fellow of the American College of Trial Lawyers and a member of many professional associations. A Methodist and a Mason, Gray was survived by his wife, a daughter, and two grandchildren.
At Gray’s death District Commissioner Walter N. Tobriner remarked, “‘The District of Columbia will feel a deep loss in the passing of Chester Gray. For the greater portion of his life he served the city with an unflagging zeal and tremendous learning in the law. The Commissioners have lost a most valuable servant and the community a protector of the rights of all.”’
The 'Washington Post' praised Gray’s “extraordinary tact and patience” as “indispensable assets,” and opined that “Chester Gray’s long and dedicated service to the District of Columbia richly deserved” Tobriner’s “warm tribute.” Gray consistently received strong performance evaluations, which characterized him as “a prodigious worker” of “exceptional competence” and “devotion to duty” who handled even the most difficult cases with “outstanding diligence, tact, and professional skill.”
He also was credited with inculcating “high standards of practice of the law and public service” among his subordinates while engendering “extremely high” morale among his staff. A memorandum in his employment file observed that he had “guided the District of Columbia through many stormy incidents, untied numerous legal knots, drafted much important legislation, handled major litigation of the community, and ably and brilliantly defended in court the District, its officers and employees.”
The memorandum praised Gray for driving loan sharks out of the District, and for contributing “substantially to the legal position taken in Berman v. Parker,” the Supreme Court’s landmark 1954 eminent domain decision.
Not everyone took such a favorable view of Gray. Earlier in 1965, the local ACLU had called for Gray’s removal over dissatisfaction with his enforcement of the District’s fair housing law, which Gray had drafted. Critics also charged that the District’s fair employment law, drafted in part by Gray, was insufficiently tough, and denounced his failure to pursue injunctive relief rather than exclusively criminal penalties against violators. George Washington University Professor Monroe Freedman mounted a bumper‐sticker campaign calling for Gray’s ouster. When Tobriner was named president of the District’s Board of Commissioners in 1961, “the Democratic Central Committee asked him to fire Gray, considered by some Democrats to be too reactionary for the 1960s.”
At the same time, the House of Representatives District Committee, headed by Democrat John L. McMillan of South Carolina, launched an investigation into whether the District Commissioners had exceeded their authority by banning racial discrimination in housing, employment, and at barbershops. Each of these prohibitions had been enacted based on Gray’s legal opinions that the Commissioners in fact possessed such authority.
Gray’s obituary in the 'Washington Post' opined that it was “ironic that most of the criticism directed against Mr. Gray’s office in recent months has been mounted by civil rights groups charging that the office drags its feet on regulatory interpretations in the civil rights field, because Gray’s associates thought that he would be longest remembered for his work with the so‐called ‘lost’ segregation laws before the United States Supreme Court.”
The litigation referred to, District of Columbia v. John R. Thompson Co., involved the questions of a) whether the Legislative Assembly of the District of Columbia had been authorized by the Organic Act of 1871 to enact an 1873 law prohibiting certain businesses from refusing to serve persons on the basis of race, and b) whether that law had survived subsequent enactments, including congressional statutes reorganizing the District’s government. The case was a prosecution by information against the Thompson restaurant chain, which refused to serve African‐Americans. The Municipal Court had quashed the information on the ground that the Act had been repealed by subsequent legislation, but the Municipal Court of Appeals had reversed on that count. On cross‐appeal the Circuit Court of Appeals for the District of Columbia held that the Act had been repealed and that the information should be dismissed. Chester Gray argued the case for the District before the Supreme Court on certiorari, and a unanimous Bench (Justice Jackson not participating) held that the law was valid and still in effect.
The 'Post' obituary remarked that “Mr. Gray argued the validity of the ‘lost’ laws and was vindicated in the landmark opinion that reversed the United States Court of Appeals,”and a memorandum in Gray’s employment file credited Gray with taking up “the cudgels against discrimination.” “He researched the law, concluded that the enactments of 1872 and 1873 prohibiting discrimination in restaurants were still valid, though they had lain dormant for seventy‐five years, and fought through all the courts. Thus, Mr. Gray, through persistent effort, made the first great contribution the striking down of race barriers in Nation’s Capital.”
When Gray died, 'Washington Post' editorialized that “what the city needs is precisely the kind of legal pioneering Chester Gray displayed more than a decade ago when he discovered and disinterred and breathed life into those ‘lost’ segregation laws in the Thompson Restaurant case.”
Although it is largely forgotten today, the Chicago-based John R. Thompson company was one of the largest “one arm” lunchroom chains of the early 20th century. We so strongly associate fast food chains with hamburgers that it may be surprising to learn that Thompson’s popular sandwiches included Cervelat, smoked boiled tongue, cold boiled ham, hot frankfurter, cold corned beef, cold salmon, and Herkimer County cheese, served on “Milwaukee Rye Bread” baked by the chain’s bakery. Thompson was proud that his meals were suited for sedentary office workers of the 1900s and 1910s. A 1911 advertisement claimed that lunch at Thompson’s “won’t leave you logy and lazy and dull this afternoon.”
John R. Thompson’s business would ultimately go down in history as one that refused to serve Afro-Americans. Or, as civil rights leader Marvin Caplan put it in 1985, “If the chain is remembered today, it is not for its food, but for its refusal to serve it.”
J. R. died in 1927. Where he stood on the question of public accommodations is unclear but the chain faced numerous lawsuits by blacks in the 1930s.
However the best known case occurred in 1950 when a group of integrationists led by Mary Church Terrell was refused service in a Washington D.C. Thompson’s. The group was looking for a case that would test the validity of the district’s 19th-century public accommodations laws.
After three years in the courts the Thompson case (for which the Washington Restaurant Association raised defense funds) made its way to the Supreme Court which affirmed the so-called “lost” anti-discrimination laws of 1872 and 1873 as valid.