Born to a prominent attorney in New York, Stewart studied law in Minnesota and became the first African American lawyer in the state of Oregon.

Living in the era of Plessy v. Ferguson and "separate but equal" doctrine, his life was said to "reflect an unyielding commitment to the principle of justice for all powerless people in the northwest.

His brother, Gilchrist, would also become and attorney and his sister, Carlotta Stewart Lai, would help develop Hawaii's public education system.

A strong follower of Washington's principles, Stewart's father operated his office and his business relationship with his son under strict guidelines.

He required that his son sign a contract which specified his employment and compensation in detail, noting that "my intention is to pay you $3 per week to cover your fare, lunches; allow you 5% of all my fees; at 21, I shall make you Notary Public and put your name on the door.

His reason for choosing a northern school in a state with a small black population was never revealed, however the change in environment gave Stewart a new sense of purpose and maturity.

Unlike his years at Tuskegee, he was a model graduate student in Minnesota: he excelled academically, wrote from the school newspaper and was an active member of a literary society.

[2] During his senior year, his fellow Tuskegee alumnus and University of Minnesota Law student Jay Moses Griffin recruited him to work as business manager of a local newspaper, the Twin-City American.

Several other patrons observed the incident and left their names with Stewart, who filed an administrative complaint with the Minneapolis City Attorney's Office under the recently passed 1897 state civil rights law.

[4] That June, alongside his classmates, Stewart was sworn into the state bar by Minnesota Supreme Court Chief Justice Charles M.

[4][11][12] In the years immediately following his graduation, Stewart continued to make his home in Minneapolis and speak to crowds in the Twin Cities.

He was allowed to represent clients in local Portland courts before passing the bar examination, and was assigned as the public defender in a few cases in 1903.

[4] Stewart disregarded the advice and remained in Oregon, and was the first African American admitted to the state bar on March 1, 1901.

[4] The case involved Oliver Taylor, a black Pullman car porter, who was required to sit in the balcony at a Portland theater.

When informed that the theater prohibited the seating of blacks on the main floor, the plaintiff refused to exchange his tickets and sued the owner for $5000.

The state's largest newspaper, The Oregonian, sided with the theater owner's right to exclude any race from its premises; it editorialized that "Colored people are wise to accept conditions that they cannot change or control, and go their way cheerfully", further asserting that "it is a well known fact" that whites objected to sitting next to blacks.

Believing he had done no wrong, Stewart objected and the policeman arrested him and made him walk a mile on his prosthetic leg to the police station where he was booked for drunkenness.

Authorities refused to charge Stewart, and the next day he filed a complaint of assault and battery with the district attorney, who issued an arrest warrant against the officer.

Democratic Governor George Earle Chamberlain appointed him as Oregon's representative to the 1908 National Negro Fair in Mobile, Alabama, where he gave a keynote address.

[4] He was then appointed by Chamberlain as chief commissioner to the National Emancipation Commemoration Society, organized by President William Howard Taft in 1909.

[4] A few months after moving to San Francisco, Stewart had to return to Oregon to close his office, bring his family to California and finish the appeal of his final Oregon case, Allen v. People's Amusement Co. Just like Taylor eleven years earlier, the case involved a black patron denied seating in the white section of a Portland theater despite his purchase of a general admissions ticket.

[2] Upon returning to California, Stewart's optimism for San Francisco was short lived: despite the larger black professional class, there was little affluence and even more racial segregation than in Portland.

[4][22] On April 14, 1919, unable to read his morning newspaper and fearing that he was about to go blind, Stewart wrote a note of farewell and shot himself in the head in his office.

[2] Although Stewart followed many of Booker T. Washington's philosophies of self-reliance, industriousness and good citizenship, he also differed by actively advocating for civil rights for African Americans in an era when discrimination was high.

During its inauguration, J. Clay Smith, Jr., former dean of the Howard University School of Law, noted that "Despite the ominous shadow of segregation, Stewart refused to sacrifice his principles at the expense of his clients or to derogate his beliefs.

Mary Katherine Stewart-Flippin donated her family's papers, including those of her grandfather T. McCants Stewart, her father, and her husband to Howard University.