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The Grand Master of Political Cartoons
B. Chris Ruli Grand Lodge Historian
On November 16, 1902, Washington Post illustrator and D.C. Freemason Clifford K. Berryman published the political cartoon “Drawing the Line in Mississippi.” The cartoon depicts President and Brother Theodore Roosevelt declining to shoot a chained bear while on a hunting expedition. The scene was based on an incident days before when Roosevelt arrived in Mississippi to arbitrate a territorial dispute between the state and neighboring Louisiana. The President agreed to join a hunting competition during his stay but declined to shoot a chained black bear for sport. Berryman’s illustration “went viral” (to borrow a contemporary phrase) and caught the attention of New York toy manufacturer Morris Mitchtom. Mitchtom quickly developed a prototype of “Teddy’s Bear” and received the President’s permission to use his name. This topical toy evolved into the Teddy Bear we know today. As for the toy’s “creator,” Worshipful Brother Berryman became so enamored with his beloved illustration, which he affectionately named Bruin, that he added him in future illustrations. Berryman and Bruin would remain a fixture not only in Washington politics and society, but also in D.C. Freemasonry for another four decades.
Berryman was born on April 2, 1867 in Woodford County, Kentucky. He inherited his father’s talent for caricature and later worked as a draftsman in the U.S. Patent Office where he developed highly technical patent illustrations. Avid in politics, Berryman often submitted cartoons to the Washington Post for consideration. This became a lucrative hobby for him as each published submission would garner him about $25, or more than a week’s salary at the patent office. Impressed with his skill, Washington Post Illustrator George Y. Coffin, a member of La Fayette Lodge No. 19, invited Berryman to serve as his understudy. When Coffin died in 1896, Berryman succeeded as the Post’s full time Illustrator until 1906 when he transferred to the Evening Star.
Like his predecessor, Berryman won critical acclaim and praise for his illustrations, which expertly summarized complex and timely editorial commentary - often down to a single panel. His cartoons targeted politicians indiscriminately and covered broad topics including local and national politics, campaigns and elections, international affairs, war, and early pop-culture. He was the Gridiron Club’s first cartoonist and served as their president in 1926. In 1944, he was awarded the Pulitzer Prize for his cartoon ‘But Where Is the Boat Going?’ — a commentary on the U.S. mobilization efforts during the Second World War.
Berryman began his Masonic career in Washington Centennial Lodge No. 14. He was initiated on January 6, 1892, passed February 3, and raised March 3. He served as the Lodge’s Master in 1897, and later joined other zealous Masons on December 18, 1907 to charter Temple Lodge No. 32. His interest in Masonry progressed and he rose up the ranks of the York Rite and Shrine, becoming a member of Washington Commandery No. 1, Knights Templar, and Almas Shrine, respectively. Berryman served on several Grand Lodge committees, most notably the Library and Museum committee, during the period where the Grand Lodge set up its membership card catalog. (See Vol 38, Issue No. 2 of this illustrious publication for more on the card catalog.) Among his original works, carefully preserved in the Library of Congress, we find several Masonic-theme illustrations that capture the spirit of Freemasonry while weaving in topical political commentary.
In fact, his Masonic illustrations were often infused with political commentary. Certain cartoons called upon the District’s Freemasons to help address local political issues, most notably, on the question of D.C. voting rights and statehood. When sojourning Shriners arrived in Washington for the Imperial Shrine’s Sessions, Berryman published several cartoons reminding some of the convention’s most prominent Shriners (some of whom were members of congress) to help D.C. obtain a vote. More lighthearted illustrations captured the excitement and grandeur of Masonic events including the National Masonic Fair and Exhibition. (See Vol 37, Issue 3 of this publication for more on these incredible fairs.)
Berryman serves as a classic example of a prominent Washingtonian who left a lasting impression on the District and the Fraternity. His professional work stands the test of time and serves as a guide for future generations to understand complex political commentary through caricature. As a Freemason, he appreciated the Fraternity’s values and principles and served his lodge as Master and later through Grand Lodge committees. His lasting contributions are perhaps best summarized by another prominent Freemason, Harry S. Truman, when on Berryman’s 80th birthday, Past Grand Master Truman wrote to him and said: “You are a Washington institution comparable to the Monument. To me you are ageless and timeless. Presidents and Senators and even Supreme Court Justices come and go, but the Monument and Berryman stand.”
Clifford Berryman

Berryman’s depiction of the 1902 National Masonic Fair and Exhibition held in D.C. The jurisdictional event was organized across the Grand Lodge, York and Scottish Rites, Shriners, and Order of Eastern Star to raise money for a new Masonic temple.

Berryman acknowledges the Shrine’s efforts to support children through hospital programs.

Theodore Roosevelt Teddy Bear George Washington (representing D.C.) and Bruin, both dressed as Shriners, march in the Shriner parade with the US Capitol in the background. Bruin holds a banner reminding the reader that DC Shriners proudly march in the parade, even though they’re the only jurisdiction that doesn’t have voting representation in Congress.


A soviet farmer envisions an American Shrine parade through Washington. He acknowledges that his efforts to lobby Shriners on communist ideology would garner little success.

Uncle Sam congratulates George Washington (representing D.C.) on organizing a great Imperial Session in the city, but Washington reminds him that the District still doesn’t have a vote in Congress.