In the Beginning
TR was born October 27, 1858 three years before the Civil War. He’s the only president who was born in Manhattan.
The Roosevelts lived on 20th Street. They made their money importing glass and mirrors. Their business Roosevelt & Son at 97 Maiden Lane is a short walk from Wall Street.
TR began life slowtly. He was born with bad eye site and struggled with asthma. To help him breath the doctors gave him whiskey to drink and cigars to smoke. In the mid-19th Century practitioners believed nicotine helped cure asthma. You could buy asthma cigarettes.
His father told him if he was going to succeed in life he needed to get stronger. He built a small gym for TR where he could lift weights, box and exercise. He worked tireless keeping a detailed chart of his progress. He began living what he called the “Strenuous Life.” He said he never wanted to rust out, he wanted to wear out. The asthma slowly began to fade away.
He had an older sister Anna who was born with Potts disease (spinal tuberculosis). It’s where bacteria attack and weaken the vertebrae progressively leading to permanent disability, Despite her setbacks she was the Roosevelt rock. When there was a crisis everyone sought Anna’s advice.
TR’s younger brother Elliott was the father of Eleanor Roosevelt and his younger sister Corinne grew up best friends with Edith Kermit Carow the future First Lady.
To escape the summer heat the Roosevelt’s traveled to Europe, the Jersey shore and upstate New York before coming to Oyster Bay when he was 15. In town his father rented a home named Tranquility owned by Gabriel Irving the nephew of Washington Irving.
In Oyster Bay he’d hike, ride, swim, hunt, camp, fish, explore Center Island and row across the Long Island Sound. One day he got caught in a storm rowing from Oyster Bay to Throgs Neck and back. He didn’t return home until nearly midnight.
The future First Lady would visit from NYC. She’d take the L.I.R.R. to Syosset where the Roosevelt’s had a carriage waiting to take her to Oyster Bay. The two families knew one another. Their fathers toured Europe together. Edith Carow lived around the corner and growing up Edith and TR played together. For a brief time Edith was home schooled at the Roosevelt's. She and TR would read stories to each other on the front stoop. Over the Oyster Bay summers their friendship developed into a teenage romance.
TR spent much of the summer of 1876 being tutored by Arthur Cutler preparing for the Harvard entrance exam. In his freshman and sophomore years at Harvard TR and Edith remained close until August 22, 1878 when TR proposed to Edith at Tranquility. Neither family wanted to see the two get married. Edith's grandfather Daniel Tyler IV whose portrait is on the second floor at Sagamore Hill between the Master Bedroom and the Gate Room, forbid any engagement. It was partly because he believed Edith was too young and partly because he wrongly believed the Roosevelt's had a history of bacterial infection that caused the lymph nodes to swell and break open. TR's father forbid the marriage because he believed the Carow's had a history of alcoholism. Edith's father was an alcoholic. According to the families TR proposed to Edith several times, but whatever happened at Tranquility nothing went right. Edith had just turned 17 two weeks earlier and perhaps her age was a factor and perhaps some of what their families said came up in the conversation. Whatever it was tempers flared and the relationship ended.

Returning to Harvard TR fell head over heels for Alice Hathaway Lee the daughter of a wealthy banking family in Boston. In 1848 the lees’s established the successful investment firm of Lee, Higginson & Co. In 1892 the firm was instrumental in creating General Electric. In 1910 they helped build a struggling General Motors. Philanthropically they were influential in founding the Boston Sympathy Orchestra. By any measure the Lee’s were far wealthier than the Roosevelts.
In his junior year, hoping to impress Alice, TR spent more money on clothing than most students spent on tuition. He bought dueling pistols in case anyone challenged their romance.
TR proposed to Alice in June 1879. She told him she was unsure of her feelings and at that time she couldn’t commit to marriage. TR didn't give up. He waited 6 months and in January 1880 he asked a second time. Alice accepted. They announced their engagement on Valentine’s Day and married on his 22nd birthday. They spent their honeymoon night at the Massasoit House on Main Street in Springfield, Massachusetts before heading to Tranquility. A formal honeymoon had to be delayed until TR finished his first year studying law at Columbia. In the Spring when classes ended he and Alice embarked on a 5 month tour of Europe.
Two months after their marriage ceremony TR buys 60 acres in Cove Neck from Thomas Young’s. In August 1883 when Alice was 3 months pregnant TR buys an additional 95 acres on a windswept hillside looking over oyster Bay with the intention of building an estate for Alice called LeeHolm.
All in all he would own 155 acres. He then sold 28 acres to his sister Anna and 32 acres to Aunt Anna Bulloch Gracie (James Gracie - Gracewood). He kept 95 acres at a cost of $20,000 mortgaged.
He then spent $16,975 building a 22 room country house with a windmill and ice house. He then spent $5,160 to build a Lodge and Stable and another $19,000 to add the North Room extension in 1905.
When it was all said and done TR had spent $63,135 (his entire inheritance from his mother’s estate) to create Sagamore Hill which is about $1,400,000 in todays money.
After Alice died in 1884 and he began dating Edith he changed the name to Sagamore Hill for an old Indian chief named Sagamore Mohannis who signed away the rights to the land 250 years earlier.
They began building the house in March 1884 and finished in May 1885 making it a year older than the Statue of Liberty and a year younger than the Brooklyn Bridge. It became the first Summer White House in American History.
It was owned by the Roosevelt’s for 70 years. After Edith’s death the family sold Sagamore Hill to the Theodore Roosevelt Association for $175,000 in 1950. ($2,350,000 Today).
The Theodore Roosevelt Association opened the house to the public on Sunday June 14, 1953. They kept it in their care for 12 years before gifting Sagamore Hill along with a $500,000 endowment to the National Park Service. The transfer was authorized on July 25, 1962 and the park was established a year later on July 8, 1963.
