In a bizarre true crime story too weird to believe, FDR's son Elliott was accused of
hiring a hitman to assassinate the Governor of the Bahamas. But why?
Anna Roosevelt was the eldest child and only daughter of President Franklin Roosevelt and his
wife Eleanor. Anna became a writer and journalist, and in 1935 she married her second husband,
journalist Clarence John Boettiger. The couple got their break when newspaper magnate William
Randolph Hearst offered them both jobs at the Seattle Post-Intelligencer. Hearst made Boettiger
publisher, giving him a platform to support FDR politically — even when Hearst broke with
the president. But the couple was a package deal, meaning Hearst had to give Anna a job,
too. He had the perfect one, making her an associate editor in charge of the "women's pages."
That chapter of their lives ended when World War II broke out. Boettiger signed on with
the U.S. military in 1942, and a year later Anna returned to the White House. In the White House,
she acted as de facto first lady and White House hostess. Her mother was too politically active to
be bothered with social functions, so Anna served in her stead. Given her role as Roosevelt's social
secretary, Anna asked to accompany her father to the 1945 Yalta Conference, where he met with
Joseph Stalin and Winston Churchill to decide the fate of post-war Europe. President Roosevelt,
who was dying of heart disease, had the option of picking either Eleanor or Anna.
For the president, the decision was easy. His marriage with Eleanor was on the rocks,
particularly as rumors swirled about his affair with Lucy Mercer Rutherfurd,
so he put Anna on the delegation to avoid bringing her mother. At Yalta,
Anna's job was to make the ailing president's life as easy as possible, mostly by ensuring that
social functions ran smoothly so FDR could focus on his duties without compromising his health.
"Prime Minister Churchill arrives with his daughter. They are greeted by Mrs. Boettiger."
However, the conference and its aftermath resulted in friction with her mother. In 1945,
President Roosevelt died. Naturally, Anna told her mother of the circumstances of the death,
including a revelation that may have stung Eleanor:
FDR had spent his last moments with Lucy. Anna had known about the affair for years,
but concealed it from her mother, who took it as a personal betrayal of sorts.
Following her father's death in 1945, Anna reprised her media career,
purchasing an Arizona weekly newspaper alongside her husband. They had turned
it into a daily by 1947, and although there was some initial success, the venture failed,
leaving the couple indebted. The venture strained the marriage, leading them to separate and
eventually divorce in 1949. Three years later, her third marriage to James Halsted saw her pivot to
non-profits and international organizations. She died in 1975 of cancer at the age of 69.
James Roosevelt took a series of jobs and military service with the elite "Carlson's Raiders" in the
Pacific during World War II, before returning to the United States to pursue a political career in
California. In California, James remained a Democrat. But he got himself in trouble
with the party for supporting Republican Dwight Eisenhower, defending Richard Nixon, and endorsing
Ronald Reagan's 1980 and 1984 presidential bids. Roosevelt justified his endorsement
by claiming that Reagan was the best choice to continue Franklin Roosevelt's New Deal legacy.
But in 1987, the Los Angeles Times reported that James' "National Committee to Preserve Social
Security and Medicare" was facing accusations of running a "fund-raising scam that degrade[d]
the Roosevelt name." It allegedly used scare tactics to solicit donations from the elderly,
who depended upon both programs. The PAC argued that both programs risked major
solvency crises down the road, and the House Ways and Means Committee summoned James to testify.
The incident revealed a break between James and
the Reagan administration's policies. The PAC's executive director, Landis Neal,
made it crystal clear that donors to the organization were "frightened
by the Reagan administration," presumably a reference to various cuts to social services.
The scandal followed James until he died in 1991 at the age of 83.
In 1909, the future presidential couple lived in New York City with their two children, Anna
and James. That year, Eleanor Roosevelt wrote in her 1937 memoir "This Is My Story" that she gave
birth to a third, forgotten Roosevelt child — the first Franklin Roosevelt Jr. — in March of 1909.
Eleanor wrote that this child was, quote, "the biggest and most beautiful of all the babies."
For the first few months of his life, he was mostly under the care of nurses. He seemed to
be doing fine, despite his mother's worries that he would be a difficult child. But in November,
he, along with his two siblings, contracted the flu. A doctor's visit confirmed that he
had sustained heart damage, and the child died. Eleanor, in her memoir,
regretted not having spent more time with the child, and blamed herself for his death. She even
wrote that at the funeral, it seemed "cruel" to "leave him out there alone in the cold."
The child was buried at St. James' Episcopal Church in Hyde Park, New York. But in December,
1909, Eleanor found herself pregnant again with another son, Elliott Roosevelt.
Elliott Roosevelt was known as Franklin Roosevelt's "Black sheep" son,
as he was involved in all sorts of weird hustles.
"Did you ever sell Christmas trees?"
"Yes!"
"Did he?"
"Yes!"
But his shady reputation was mostly earned through involvement in various contracting
scandals involving aircraft. The first scandal occurred in 1934 and dropped in the press in
1936. The younger Roosevelt had entered into an agreement with Dutch aviation company Fokker to
sell military aircraft to the Soviet Union, disguised as civilian planes,
through a shell company set up by Elliott Roosevelt. They would split the profits.
A scandal brewed because the plan stank of influence peddling. Elliott had taken
the deal knowing that foreign governments would be more open
to working with him because he was the president's son. The president objected,
but did not stop him. Elliott denied any financial exchange or illegal conduct,
noting that the deal collapsed before payment because the Soviets backed out.
The second scandal came in 1943, when Howard Hughes tried to sell the government
a new photo reconnaissance airplane. He had the support of Elliott Roosevelt,
then a colonel in the Air Corps. The allegation was that the first son had once again put his
thumb on the scale in a quid-pro-quo arrangement with Hughes. Hughes' agent John Meier wined and
dined Elliott, spending over $5,000 for him to meet beautiful women at New York's most
exclusive clubs — presumably in return for getting the military to buy Hughes' plane.
Roosevelt denied all wrongdoing, saying he had been abroad when Meier's records had them meeting.
"Did any of those girls who were paid, were they procured for my entertainment?"
Later in life, Elliott Roosevelt faced a fresh scandal involving an alleged contract killing.
On September 18, 1973, Louis Mastriana, a man previously convicted of securities fraud,
testified to the Senate that Elliott Roosevelt had been part of an alleged
plot to kill the governor of the Bahamas, Lynden Pindling.
The dispute at the center of the alleged plot was straight out of
the world of organized crime. Pindling had allegedly reneged on a promise to give a
casino license to one Mickey McLaney in return for a $1 million donation.
McLaney reportedly had connections to some very dangerous people, including Murder,
Inc. honcho Meyer Lansky. Mastriana testified that Elliott Roosevelt offered him $100,000, including
$7,500 upfront in cash and a $2,500 check from McLaney to "whack" the Bahamian governor.
Weeks later, The New York Times reported that Elliott appeared in Washington to refute the
charges, calling them "vicious lies" resulting in "emotional, physical and financial stress beyond
endurance." He further called Mastriana's claims a hoax and demanded he be prosecuted. The evidence
was inconclusive. A check made out to Mastriana was entered into the congressional record,
so there was no doubt that Roosevelt had associated with him. But there was no way
to determine whether the money was for the alleged hit job, which Mastriana claimed
was called off because it would be impossible to escape the Bahamas quickly to cover his tracks.
Eliott Roosevelt died in 1990 at the age of 80.
The second Franklin Roosevelt Jr. survived infancy and went on to have a distinguished
military career, after graduating from Harvard and the Navy ROTC program. When the United
States entered World War II in 1941, he signed on to the U.S. Navy. He was posted to Europe,
where he was granted no favors as the president's son and cast into the thick of the action.
Roosevelt's commission brought him first to North Africa and then to Sicily in 1943. Then,
he was a lieutenant on the USS Mayrant, where the crew affectionately called
him "Big Pancho." In Sicily, he earned a Silver Star and Purple Heart for heroism
during a German air raid against the Sicilian capital, Palermo.
The original military citation reads that Roosevelt Jr. was decorated for
"conspicuous gallantry and intrepidity in action." German bombers struck explosive
munitions sitting near the docks, causing an explosion and sending shrapnel towards
the Maynard. As the bombs continued to fall, the first son rushed to help two wounded crewmates,
giving them first aid under fire and carrying them off the ship to safety, saving them.
After Palermo, FDR Jr. was transferred to the Pacific alongside a promotion to
lieutenant commander, the USS Moore destroyer to command, and a new nickname — "Big Moose."
He saw action in the Philippines, Iwo Jima, and Okinawa, earning another battery of decorations
there. After the war, he represented New York in Congress on a third-party ticket and headed
the Equal Employment Opportunity Commission under Lyndon Johnson. He died in 1988 at the age of 74.
John Roosevelt was FDR's youngest child and a bit of a political maverick. His
brothers all held political office: Elliott was mayor of Miami Beach,
while Franklin Jr. and James were congressmen and federal bureaucrats
in the Democratic Party. John broke with family tradition on both counts.
Unlike his siblings and much to their chagrin, John was a Republican,
making his party affiliation official in 1947. He also never held political office:
The closest he ever came was considering a run for the mayoralty of New York City
in 1957. He preferred to support candidates, lending his financial muscle and influence to
Dwight Eisenhower, Ronald Reagan, and most annoyingly for his family, Richard Nixon.
John became a successful businessman. He died from heart failure in 1981 at the age of 65.