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It Happened In Syosset! - April 2, 2010

Part 3: The Syosset Farmer Who Would Have Shot TR?

(Editor’s Note: This is the third in a multi-part series by Tom Montalbano highlighting some of Syosset’s most shocking and most forgotten events.)

Twenty-eight-year-old Henry Weilbrenner, Jr. was the son of a German immigrant “truck farmer” who owned a 72-acre parcel of land on the west side of Jackson Avenue, encompassing what is now De Benedittis Nursery and the surrounding area. One of three brothers, Henry played a significant role in his family’s daily grind, which included hauling a large, horse-drawn wagon (truck) into Brooklyn or Manhattan each day to hawk fresh produce to restaurant owners, cruise ship purchasing agents, and servants to Manhattan’s elite. To balance the tedium and stress of his day-to-day routine, Henry apparently manufactured an imaginary love affair with Alice Roosevelt, the daughter of the 26th President of the United States, for whom the fantasy almost turned deadly.

A Young Man Falls in Love

Truck farming was a grueling life that could take a heavy toll on a man’s nerves. For the Weilbrenners of Syosset, life had become even more difficult at the onset of the twentieth century, as they had fallen into debt on their farm and had spent the next few years struggling to hold on to their investment. For Henry Weilbrenner, Jr., namesake of the farm owner, the pressure was sometimes debilitating.

At one point, Henry Jr. suffered what his family described as a “nervous attack which rendered him mentally helpless for a day or two.” However, the Weilbrenner family believed that medical treatment he had received at the time had cured him, as he had managed to keep up with his farm duties and stay out of trouble around Syosset for a number of years.

Unbeknownst to his family, in his mid-twenties, Henry Jr. developed an infatuation with Miss Alice Roosevelt, the very attractive daughter of President Theodore Roosevelt. Roosevelt, who maintained a “Summer White House” at Sagamore Hill in Oyster Bay, commonly visited Syosset to use the railroad station or to chat and smoke cigars with friends along Jackson Avenue. Alice, a product of Roosevelt’s first marriage, had risen to celebrity status both for her bold fashion sense and her “bad girl” behavior. In what family members described as an attempt to win her father’s attention, Alice constantly went out of her way to break common social rules for women, smoking cigarettes in public, staying out late partying, and even placing bets with a bookie. At one point during his presidency, TR was heard to declare “I can either run the country or I can attend to Alice, but I cannot possibly do both!” To some, Alice was a detriment to TR’s presidential image, but to a young, unsophisticated farmer such as Weilbrenner, her antics apparently stirred up quite a bit of excitement.

An Unconventional Marriage Proposal

Weilbrenner’s obsession crossed the line late in the evening of September 1, 1903, when he arrived by horse and buggy at the gate of Sagamore Hill dressed in a dapper black suit and an old-fashioned derby hat and advised the Secret Service operative that he had a “personal engagement” with the president. The agent, accustomed to turning away aggressive newspaper reporters and star-gazers, tactfully advised Weilbrenner that 10:00 p.m. was long past the hours when the president normally accepted visitors and that he could not let him through the gate. Weilbrenner persisted somewhat, but eventually turned his carriage around and rode away.

A short while later, Weilbrenner returned and insisted that he be allowed to see the president, if only for a minute. After refusing several times to answer why he needed to see the president, Weilbrenner reportedly snapped “None of your damned business!” This time, the Secret Service agent ordered him away from the property and warned him not to return.

The agent’s directive apparently did not dissuade Weilbrenner for very long. At approximately 11:00 p.m., as Roosevelt finished some work in his study, Weilbrenner appeared for a third time and demanded that he be permitted to see the president, “at once!” When the agent again refused him, Weilbrenner proceeded to create a commotion that drew the president out to his porch, less than 100 yards from the gate.

Upon glimpsing the president, Weilbrenner whipped up his horse as if to make a dash for the house. Instinctively, the agent jumped on the buggy, dragged Weilbrenner over the front wheels and brought him to the ground. As the president ran back into the house, the agent subdued Weilbrenner and hauled him to a barn on the property. There, he placed him under the armed watch of two stablemen while he secured the president’s home and searched Weilbrenner’s wagon, in which he found a fully loaded revolver.

Alarmed that the President of the United States might be under attack, the agent summoned five additional Secret Service operatives who were lodging at the Octagon Hotel in Oyster Bay. Upon arrival by horseback, the team conducted a full search of the grounds and the surrounding area, but found no evidence of accomplices. They then removed Weilbrenner from the stable and transported him, via a special Long Island Rail Road car, to the County Jail in Mineola, where he was locked up overnight.

Inside the Mind of a “Demented Farmer”

At his arraignment at the Nassau County Court the following day, Weilbrenner remained calm and collected as he explained the reason for his visit to Sagamore Hill.

“I went to see the president about his daughter.” Weilbrenner stated, matter-of-factly.

Asked if he had an appointment with the president, Weilbrenner responded “Yes. I talked with the president last night.” Questioned as to how he contacted the president, Weilbrenner answered “Oh, I just talked.”

The investigating officer then asked Weilbrenner if his family owned a telephone, to which he responded, “No.” At this point, the officer remarked, perhaps mockingly, “A sort of ‘wireless’ talk then, was it?”, evidently referring to the new wireless communication technology that had recently been adopted by the U.S. Navy.

“Yes. That is it…a wireless talk,” replied Weilbrenner, who went on to explain that he and the president could talk to one another from their respective houses without the assistance of a telephone, telegraph, or radio system of any type.

“And why did you want to see the president about Miss Alice?” the examiner continued.

“Because I wanted to marry her,” stated a perfectly composed Weilbrenner.

Asked if he had ever met Alice Roosevelt, Weilbrenner advised that he had known her for about six months and that she had visited him at his house in Syosset the previous night, having driven up in a red automobile with her brother, Teddy, Jr.

Questioned as to why he was carrying a fully loaded gun when he went to see the president, Weilbrenner stated that he had been practicing his marksmanship recently, but could give no reason why. He also advised that he wasn’t a very good shot.

When it became apparent that Weilbrenner might be mentally deranged, the examiner called the prisoner’s mother, brother, and sister in for questioning. The family members told investigators that Henry Jr. had been moody recently and that, with the president and his family constantly before the public, he had become obsessed with them.

Although Weilbrenner never claimed that he intended to kill the president, the headlines of many big city newspapers reported this to be the case, describing him as the “demented Syosset farmer” and a “dangerous lunatic” who “sought the president with a loaded revolver.”

The following day, Drs. George Stewart and Irving Barnes interviewed Weilbrenner, declared him to be insane and unfit to stand trial for an attempt on the life of the president, and immediately committed him to the Kings Park Asylum.

Although Roosevelt, in speaking with the press in the days that followed, described Weilbrenner as a “poor, demented creature,” a family member later quoted him as remarking in private “Of course he’s insane…he wants to marry Alice!”

Life Goes On

Teddy Roosevelt continued to visit Syosset and to use the train station on Jackson Avenue despite the incident involving Weilbrenner, whose family auctioned off their Jackson Avenue farm and left Syosset shortly afterward.

In 1906, Miss Alice married Congressman Nicholas Longworth of Cincinnati in what has been described as the “grandest White House wedding of all” and “the most spectacular social event in all of American History.”

Six years later, Roosevelt was shot and wounded by a saloonkeeper while campaigning in Milwaukee, Wisconsin. On his return to Sagamore Hill to recover from the shooting. Roosevelt fooled the hordes of reporters at the Oyster Bay station by secretly arriving in Syosset instead.

(About the author: Tom Montalbano is the author of Syosset: Images of America, the first of two photographic histories of Syosset, as well as Steel Rails Through The Pines: The First 150 Years of the Syosset Train Station, an e-book that can be downloaded free at He is currently compiling a history of the Syosset Fire Department in honor of its 100th Anniversary in 2015.)