Born in New York City on May 3, 1906, Anna Roosevelt learned early—and embraced—the life of a career politician’s child. When her father served as Assistant Secretary of the Navy in President Woodrow Wilson’s administration, she attended the National Cathedral School for girls. In 1919 she was in a crowd of schoolgirls standing on New Hampshire Avenue, waiting for their bus home, when the British Prince of Wales, then visiting the city, stopped by and introduced himself. The prince recognized Anna by her last name and acceded to her demand that he should visit her school the following day. Later, the Prince told FDR “how he had enjoyed the entire episode.”[1]

After leaving the Cathedral School as a “tall, shy girl” in 1920, Anna attended Chapin School in New York, before returning to Washington, D.C., for her “coming out” ball in 1924. Two years later, in the midst of her studies at Cornell University, she was married in Hyde Park to Curtis Bean Dall. Anna was attended by her father, who had been recently stricken with polio, and her Belgian police dog, Chief, whom she had won in a Red Cross raffle during World War I. The couple had two children, Anna Eleanor and Curtis, but the marriage was not happy, and they eventually separated. In 1933, she and the children—who the reporters called “Sistie” and “Buzzie,” moved into the White House.”[2]

A prolific writer, Anna Roosevelt published two children’s books, several articles, and a spokesperson for mothers’ and children’s issues; in 1935—Anna became executive board chairman of the National Research Center in Washington, DC. During her tenure, she oversaw experimental nursery schools based on a “teaching by play” method, explaining that the school would focus on “learning of the right health habits; the discipline that comes from cooperative play with other children; [and] the early development of the sense of rhythm and the use of body muscles. There are stories, and music, and play, things to make, things to do, every day.” Anna even took out a design patent on a bunny doll named “Scamper,” that lived in the White House, and was the subject of one of her books. [3]

Anna divorced Dall in 1934, and married Clarence Boettinger the following year; the couple had one son. She became a frequent contributor to the Seattle Post-Intelligencer, to which her husband’s family was connected, and eventually headed its women’s page. She returned to the White House in 1944 to carry out the onerous role of First Lady, and accompanied her ailing father to the Yalta Conference in 1945. After his death, she appeared regularly on radio shows with her mother, following her interests in women’s issues and human rights. Unfortunately, Anna’s second marriage was also unhappy; Boettinger suffered from depression, and committed suicide after their 1949 divorce. [4]

Three years later, she married Dr. James Addison Halsted. Over the next years, the couple shuttled  between New York and Washington, D.C. She worked in public relations, nursed her dying mother in 1962, and served the Kennedy and Johnson administrations on women’s and human rights councils.

Anna died in 1975. [5]

One of the most distinguished children, not just in the Roosevelt family, but among all presidential families, James Roosevelt was born in New York on December 23, 1907. After attending school in Washington, D.C., during his father’s work in the Wilson Administration, James entered the Groton School in Massachusetts at the age of twelve. There, he was a noted athlete, a formidable tackle on the school’s football team, and a member of the debating team. During his subsequent studies at Harvard, he often spoke publicly on behalf of his father, then governor of New York, and an aspirant for national office.[6]

On June 4, 1930, in what was billed as “one of the outstanding events of the New York social season,” James Roosevelt married Betsy Cushing, the daughter of a famous surgeon, Harvey Cushing. It was to be the first of four marriages for Roosevelt, which produced six children. Although he entered the insurance business in Boston in the 1930s, James Roosevelt’s leanings were in politics. He assisted his father during the presidential campaigns of 1932 and 1936; in 1937, he became FDR’s presidential secretary, operated in his Cabinet, various federal agencies, and helped the disabled FDR to stand and walk during public appearances.[7]

At first derided by some (as his father had been) as a smiling non-entity, James Roosevelt quickly became a White House power broker. Some took to calling him “Assistant President,” because it was almost impossible for anyone–including leading senators–to reach FDR except through his son.

Soon, James became the target of accusations of White House nepotism; it was also suggested that he used his power and influence to boost his business interests. Adding to the controversy, was his 1936 commission as a lieutenant colonel in the Marine Corps Reserve after “receiving active duty training at sea,” although, as reporters pointed out, his “military experience is somewhat obscure”; FDR had pushed through the commission so his son could better assist him on diplomatic missions abroad. Although James left his position as presidential secretary in 1938, the innuendos would continue.[8]

In October 1939 he resigned as lieutenant colonel, and requested a re-assignment to the Marine Corps Reserve at a lower rank; this was done, and he became a captain. After Pearl Harbor in 1941, Roosevelt served in a variety of combat and staff positions with the Marines and the U.S. Army, for his service, he received a Navy Cross and the Silver Star–despite chronic health issues.

When World War II, ended, James attempted to start a political career in California, but with spotty results. Allegations of improper business dealings continued to surface, and he lost the 1950 race for governor. Five years later he was elected to the U.S. House of Representatives, and remained there a decade, until he resigned to become President Lyndon B. Johnson’s delegate to the United Nations Educational, Scientific, and Cultural Organization, (UNESCO). Later in life he switched parties, supported Richard M. Nixon, and Ronald Reagan, but faithfully campaigned on behalf of his father’s programs, such as Social Security.

He died in 1991.[9]

Born in New York on September 23, 1910, Elliott Roosevelt was among the more controversial members of an always-controversial family. Athletic like his brothers, he was a swimming champion at Hun Preparatory School in Princeton, N.J., and a guard on the football team at Groton. Officials at the latter school called Elliott a natural-born “fighter,” comparing him to his father, but in fact, he was closer to his mother. He was “the family rebel, the least tolerant of conventions and even considered rather scandalous. He hated studies, and after leaving prep school rejected college in favor of getting married and entering into business.”[10]

Nothing stuck for long. Elliott got divorced after just a year and dabbled in a few business ventures before deciding that aeronautics was his primary interest. As with his older brother James, allegations of improper business dealings also dogged Elliott, including insinuations that he illegally sold aircraft to Soviet Russia. Unlike James, he openly criticized his father’s political decisions when it suited him, earning him a reputation as “quite independent in his views.” With interests in radio, Elliott was also outspoken in opposition to the propagation of hate speech on the airwaves, stating for example, that censorship “might not be too high a price to pay if it will help insulate us against the anti-Semitic oratory” of “radio priest” Father Charles Coughlin.

Elliott’s commission as a captain in the Army Air Corps in October 1940 caused charges of nepotism to surface, with some calling it a “birthday gift” from his father. [11]

During World War II, Elliott served in several roles in aerial military reconnaissance. He claimed to have flown numerous combat missions, but those claims were later disputed. He ended the conflict as a brigadier general. Elliott Roosevelt’s postwar life was as complex as his prewar experiences had been. He wrote an exposé of his parents’ domestic lives, and nearly two dozen mystery novels that featured his mother as the sleuth.

His business activities were likewise various and led to attacks of alleged involvement in organized crime. After living at numerous locations at home and abroad; five marriages and four children, Elliot settled in Arizona.

He died in 1990.

Franklin Delano Roosevelt, Jr., was born on August 17, 1914, at his parents’ summer getaway at Campobello Island in New Brunswick, Canada. Like his brothers, he had a distinguished career in business and politics; but, unlike them, he achieved it without the same taint of controversy. As per the family tradition, Franklin, Jr., went to Groton and then entered Harvard in 1933; there, he was pursued by reporters who were eager for news of the new president’s family, and castigated by them for making a “bad impression” with “careless dress”.

Nevertheless, he pursued athletics and studied well. [12]

After graduation, Franklin, Jr., married the first of his five wives in 1937, from whom he would have five children. When he graduated from University of Virginia’s law school in 1940, his father gave the commencement address. Franklin was then commissioned an ensign in the U.S. Navy Reserve, moving into active service the following spring and promoted to lieutenant early the following year. “Every inch the sailor,” he served on destroyers in the Atlantic and Pacific, coming under fire numerous times. He was awarded a Silver Star for his conduct during a German raid on his ship during the invasion of Sicily in July 1943.[13]

After World War II, he practiced law, and entered a low-key political career serving as a delegate to the U.S. House of Representatives from 1949 to 1955. Idealistically, he proclaimed a new era in American politics and decried “big-city party organizations formerly held by irresponsible club-house loafers.” His own record was undistinguished, however, and he never again held high political office, again, even though he was associated with the Kennedy and Johnson administrations, and served as the first chairman of the Equal Employment Opportunity Commission. A successful businessman in the 1960s, he pioneered the importation of automobiles by Fiat and Jaguar into the United States.

He died in 1988.[14]

Born at Hyde Park on March 13, 1916, John Roosevelt kept the lowest public profile among all of his siblings. But his life was not without controversy. Tall and good-looking, he attended Groton and Harvard, but did not fare well under the glare of publicity. On a number of occasions, he ended up in car accidents after evenings of partying; when he was eighteen, he performed a “flying tackle” on a cameraman who had taken pictures of his brother Franklin, Jr., without permission; he pulled out the camera plates and exposed the film. In August 1937, John squirted champagne in the face of the mayor of Cannes, and then bludgeoned him with a bouquet, in what came to be called as the “Battle of the Flowers”; attempts to hush up the incident were unsuccessful, and it became a minor international scandal.[15]

John Roosevelt married Anne Lindsay Clark in 1938, and they had four children before their divorce in 1965. Unlike his brothers, John had little interest in the military. Although he dutifully registered for the draft, and said he would serve if called, he considered seeking conscientious objector status when World War II began. This dalliance was successfully quashed, however, and John became a junior officer in the Navy. Towards the end of World War II he received a bronze star for his service as a Navy supply officer in the Pacific.[16]

As a businessman, John Roosevelt shunned family connections, in favor of working his way up. He started as a department store manager, but during the Cold War, he invested in uranium. He also bucked the family trend by becoming a confirmed Republican, and campaigning for Dwight D. Eisenhower in the 1950s–despite his mother’s strenuous objections. Still, he had little interest in politics in his own right. “John Roosevelt is a businessman,” explained one newspaper account. “He’s always been that and expects he always will be. When he tells you ‘no politics’ the words have a solid ring. He likes what he’s doing and is plainly content to let others have the spotlight.”[17]

During the remainder of his life, he had various business interests; he worked, briefly, for the Teamsters Union, served on boards, and was actively involved with the Boy Scouts of New York, and the National Foundation for Infantile Paralysis.

He died in 1981.