Enter the Apprentice

The first degree of theodore Roosevelt 

First article in a multi-part series

Twenty-two days following his election as Vice President of the United States, Theodore Roosevelt submitted a petition and the accompanying $5 fee to Matinecock Lodge No. 806, F. & A.M in Oyster Bay, Long Island to begin his journey into Freemasonry. On his petition, Roosevelt listed his place of business as “Albany” and his occupation as “Governor”.

The advancement through the first three degrees of Freemasonry is an experience that requires time, dedication, and instruction. For many brothers beginning their journey, it may sometimes feel a bit overwhelming to learn something new and unfamiliar while juggling their regular vocations. It was no different for Brother Roosevelt who began his Masonic journey within 48 hours of stepping down as Governor of New York.

Investigating Committee

A well-formed investigating committee has the duty of determining whether a candidate is worthy and well-qualified to join Freemasonry. It is practical for a committee to be composed of members from various backgrounds to help communicate to the prospective candidate the expectations of him in Freemasonry. They must also be on the level with every potential member, whether he is a manual laborer or a world-famous war hero.

Longtime Manhattan attorney and presiding Worshipful Master of Matinecock Lodge, W:. Theodore A. Swan, referred the petition to an investigating committee consisting of R:.W:. William Lincoln Swan, Bro. Frank W. Bonifer and W:. William S. Moore. Their responsibilities included contacting Roosevelt’s personal references to inquire about his personality and traits, and meeting with him for a formal interview at his home in Sagamore Hill.

R:.W:. Swan was a founding member of Matinecock Lodge and may have even coined its name. Swan graduated from Princeton University in 1869 and practiced law for several years before devoting himself to horticulture, growing flowers professionally and becoming an expert in landscape gardening. He was the first commodore of the Seawanhaka-Corinthian Yacht Club in Centre Island in 1871, volunteer organist at the Presbyterian Church of Oyster Bay and a member of the Saint Nicholas Society. Swan was District Deputy Grand Master between 1904 and 1905 of the First Masonic District and was elected Worshipful Master of Matinecock Lodge nine times.

Brother Bonifer was a railway postal clerk and a member of the Kismet Temple, Ancient Arabic Order Nobles of the Mystic Shrine.

Masonic petition

W:. William S. Moore was a contractor and operative Mason, elected as Oyster Bay Town Superintendent of Highways for several years and was also the owner and proprietor of the Sagamore Garage in Oyster Bay. He was elected as Worshipful Master of Matinecock Lodge in 1898 and was a member of the Knights Templar and Royal Arcanum.

This diverse group of brothers voted favorably for initiation and advancement on December 12, 1900 and, on the same evening, Roosevelt was balloted and elected to become a member of Matinecock Lodge.

Entered Apprentice Degree

Early 20th century bank

On January 2, 1901, Roosevelt stepped into the third floor lodge room of Matinecock Lodge to be initiated into the degree of Entered Apprentice. The lodge room was located in the Oyster Bay Bank Building on Audrey Avenue and the rooms were illuminated by electric candles. The lodge began leasing the third floor in 1894, in only its second year of existence. The bank occupied the first floor and the basement included a pool hall and tobacco shop. Roosevelt was already familiar with the second floor office space, as it housed his governors’ staff when he would decamp to nearby Sagamore Hill, his primary residence since 1887.

The nine-year-old Matinecock Lodge was granted a dispensation to form a lodge in the town of Oyster Bay on July 6, 1892. “Matinecock” is a Native American term meaning “at the hilly land,” which perfectly describes Long Island’s north shore where the present town of Oyster Bay is located. The Matinecock Native American communities lived along the north shore bays and inlets, comprising twenty to thirty family groups, and assisted the first Dutch settlers with farming and harvesting shellfish.

Although W:. Theodore A. Swan was the elected Worshipful Master of Matinecock Lodge in 1900 and 1901, a list of visiting dignitaries, including two past Grand Masters, conferred the Degree of Entered Apprentice on the new brother. Presiding over the degree was R:.W:. Frank E. Haff, District Deputy Grand Master of the First Masonic District (1901-02), assisted by M:.W:. John V. Vrooman, Past Grand Master of Masons in the State of New York (1889-90); R:.W:. E.M.L. Ehlers, Grand Secretary; R:.W:. Douglass Conklin, District Deputy Grand Master of the First Masonic District (1899-1900); R:.W:. Frederick P. Morris, Grand Treasurer and M:.W:. John Stewart, Past Grand Master of Masons in the State of New York (1895-96).

Eighteen of the twenty lodges in the First Masonic District sent delegations to Oyster Bay on this cold, winter night with up to 46 separate lodges represented, joined by several past and present Grand Masters and other Masonic dignitaries. The many visitors in the room were witnessing the only time an elected Vice President of the United States has been initiated into his Masonic journey.

William H. Baldwin, President of the Long Island Railroad provided special trains to the nearby Oyster Bay train station for the expected influx of visitors to the small town on the north shore of Long Island. W:. Theodore Swan advanced the $25 fee for a string quartet to perform music during the degree. There is no record of a banquet before or after the ceremony.

Part of the Entered Apprentice degree ceremony includes the presentation of a white lambskin apron to the new brother, an emblem of innocence and badge of a Mason, to be placed on the remains after his passing. Brother Roosevelt’s apron lists him as “Colonel Theodore Roosevelt, Matinecock 806 F. & A.M. January 2, A.L. 5901”. His pride as leader of the Rough Riders in the Spanish American War was on full display, overshadowing his other accomplishments up to 1901. Brother Roosevelt never had a Masonic funeral service and his apron is housed in the archives at the Sagamore Hill National Historic Site.

Masonic lambskin apron
Masonic lambskin apron

When Brother Roosevelt was sworn in as Vice President on March 4, 1901, he was the first Entered Apprentice that would reach the second highest office in the land. Although President William McKinley was a Freemason for almost 35 years, the newly elected ticket would not be the first pair of Masonic brothers to be sworn in as President and Vice President at the same time. That distinction belongs to Brothers James Monroe and Daniel D. Tompkins in 1817. Brother Roosevelt is also the only President to be preceded and succeeded by two Masonic brothers: McKinley and William H. Taft.

Brother Roosevelt’s Fellowcraft Degree would take place on March 27, 1901, twenty-three days after he was sworn in as Vice President. The next part of this series will be published in March 2021 on the 120th anniversary of Brother Roosevelt’s Fellowcraft degree. 

Written by Wor. Bro. Ronald J. Seifried, DSA
Trustee Chairman and Historian, Jephtha Lodge No. 494 F. & A.M.
Area 1 Historian, Nassau and Suffolk Masonic Districts
Co-Editor, Craftsmen Online NY Masonic History column
32° Scottish Rite,  Valley of Rockville Centre
Companion of Asharokan Chapter No. 288, Royal Arch Masons
Member of Suffolk Council No. 76, Cryptic Masons
Author, “Long Island Freemasons,” Arcadia Publishing, 2020


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