Born into one of New York’s most prominent families on January 30, 1882, Franklin D. Roosevelt survived a harrowing delivery. After his mother, Sara, received a chloroform overdose during an excruciating 24-hour labor, Franklin was born motionless. A doctor brought him to life by breathing air into his lungs.

Due to his difficult birth, Franklin would be Sara’s only child—and the focus of her attention. Franklin’s doting mother dressed the toddler in miniature sailor suits and long dresses and kept him in long curls until he was nearly six years old. Adoring Sara infused Franklin with an optimistic temperament and mandated that he always remain positive.

“I do not believe I have ever seen a little boy who seemed always to be so consistently enjoying himself,” Sara recalled. “He seemed to me always just the average carefree small boy.”

There was nothing average, however, about Franklin’s patrician upbringing on the family’s Hyde Park, New York, estate. Tutored at home and with no siblings except a half brother who was 27 years his senior (and even older than his mother), Franklin lived a sheltered life with little interaction with other children. The boy’s companions consisted mostly of his parents, governesses and family servants. “In thinking back to my earlier days,” Roosevelt recalled, “Hyde Park was the center of the world.”

In addition to teaching his son to sail and ride horseback, the pious James Roosevelt imparted to his son the moral responsibility to help those less fortunate. A prominent Democrat, James took five-year-old Franklin to the White House in 1887 to meet President Grover Cleveland. “My little man, I am making a strange wish for you,” Cleveland told the future commander-in-chief. “It is that you may never be president of the United States.”

As in many aristocratic families during the Gilded Age, Franklin was taught to avoid unpleasant subjects and overtures of emotion while striving to please others. “Franklin learned an early vigilance for any sign that he was less than delightful,” writes author Jonathan Darman in Becoming FDR: The Personal Crisis That Made a President. “And in paying careful attention to the subtle reactions of other people—a change in tone, a twitch across the face—he developed powers of emotional intuition that went far beyond his years.”

Franklin was eight years old when his father sustained a major heart attack. When doctors warned the family to shield James from any unnecessary worry, Sara taught her son to hide any negative feelings and always put on a cheerful front.

“The fact that his father suffered this heart attack when Roosevelt was a child contributed to an already strong characteristic in the family to not show emotion. They conspired to keep things on an even keel to not upset his delicate heart,” says David B. Woolner, author of The Last 100 Days: FDR at War and at Peace and a senior fellow at the Roosevelt Institute. Roosevelt’s concealment of his feelings continued into adulthood and caused the press to nickname him “the sphinx” during his presidency.

At age 14, Franklin left the cocoon of Hyde Park to attend the Groton School in Massachusetts. His cloistered childhood left him unprepared for the rigors of boarding school and living away from home, and he struggled to fit in.

Franklin didn’t excel in the classroom or on the playing fields of Groton. Fellow students thought him a lightweight. “I always felt entirely out of things,” he acknowledged many years later. Not wanting to upset his parents, Franklin choked down his complaints and never let his dissatisfaction seep into letters home.

After his father died in December 1900 during Franklin’s freshman year at Harvard University, Sara focused even more of her attention on her son and rented a house in Boston to be near him. Franklin posted a C average and wasn’t athletic enough to play varsity sports, but he served as editor-in-chief of the student newspaper. Although his stature on campus rose after his cousin Theodore Roosevelt assumed the presidency in 1901, Harvard’s most exclusive organization, the Porcellian Club, rejected Franklin in what he called the “greatest disappointment” of his life.

While at Harvard, Roosevelt fell in love with his fifth cousin once removed, Eleanor Roosevelt. Sara did not approve when 21-year-old Franklin told her of their engagement. Thinking the couple too young and unimpressed with the shy Eleanor, Sara took Franklin on a Caribbean cruise in a fruitless effort to get him to change his mind.

Eleanor’s volunteer work with immigrants living in the tenements of Manhattan’s Lower East Side opened Franklin’s eyes to poverty he had never encountered. “My God,” he told Eleanor after bringing a sick child home to a dank tenement, “I didn’t know anyone lived like that.” “I wanted him to see how people lived,” Eleanor remembered. “And it worked. He saw how people lived, and he never forgot.”

Less than two weeks after his second inauguration, Theodore Roosevelt gave away his niece at Franklin and Eleanor’s wedding on March 17, 1905. “Well, Franklin, there’s nothing like keeping the name in the family,” the president said after the nuptials. The couple went on to have six children—one of whom died as an infant—between 1906 and 1916.

While Franklin attended Columbia Law School and passed the New York bar, the newlyweds moved into a six-story Manhattan townhouse that Sara had built as a wedding gift. Their new home featured retractable doors and passages that Sara used freely to enter from an adjoining townhouse. Having inherited her husband’s estate, Sara controlled the Roosevelts’ purse strings and hired and fired staff.

As Eleanor chafed at her domineering mother-in-law, Franklin entered politics and pursued a similar path as his cousin Theodore. Following election to New York’s state senate, Franklin served as assistant secretary of the U.S. Navy and a vice presidential candidate on the Democratic ticket that lost the 1920 race for the White House. While vacationing with his family the following year, Franklin lost the use of his legs when he was stricken with polio in the prime of his life, a devastating blow that would require him to summon all the optimism and faith instilled in him from childhood in order to continue his promising political career.