Reuben Crawford was a leader in Portland's Black community from the 1870s until his death in 1918. A skilled ship caulker, he was a founding member of several political, fraternal, and religious organizations, including Mt. Olivet Baptist Church in North Portland. In 1884, he was a founding member of the New Northwest Lodge #2554, the first Black Odd Fellows lodge in the state. At the time, the Odd Fellows had "White lodges," chartered by the Independent Order of Odd Fellows, and "Colored Lodges," chartered under the Grand United Order of Odd Fellows. Crawford was also an active member of the Bedrock Republican Club, which campaigned for candidates who represented the interests of Blacks in the community.  

Crawford was born into slavery on June 12, 1828, in St. Louis, Missouri. He was enslaved by William H. Glasgow, who hired him out at the age of thirteen to work for William Thomas at the St. Louis floating docks. It is possible that Crawford never knew his parents, as Missouri law allowed slave owners to sell the children of their slaves. According to the June 23, 1914, Morning Oregonian, he "began shifting for himself when thirteen years of age."   

In 1852, Crawford married Lavinia Blue, who went by the name Vina and was enslaved by Stephen F. Summers. Having different owners and no marriage rights under Missouri law, the couple was probably forced to live apart. Any children they had as slaves would have been Summers’s property. Vina Crawford received her freedom on October 2, 1862, emancipated by her deceased owner, likely in his will. Reuben Crawford purchased his own freedom on November 1, 1862. The same year, the couple had a daughter, named Harriet. 

Reuben Crawford registered for the Union draft in 1863 but was exempted from fighting so he could build warships for the North. The January 2, 1911, Oregonian reported that Crawford helped build the USS Merrimack, an ironclad warship built for the Confederate Navy. According to his obituary in the April 10, 1918, Oregonian, however, he helped build the Monitor, an ironclad warship commissioned by the U.S. Navy. But both ships were built on the East Coast while Crawford was still a slave, and it is likely that he was not involved in either of those projects but helped build the ironclad river fleet constructed for the Union in St. Louis.

In 1867, the Crawford family—now with two sons, born in 1864 and 1866—traveled to New York and booked passage to San Francisco. They spent a year in Marysville, California, with Vina Crawford's parents, Cupid and Susan Blue, and had another daughter. In 1869, the family moved with Michael and Harriet Nye to Hood River, where Reuben worked on the Nyes's farm and Vina tended to the house. When Harriet Nye died in September 1870, her husband sold the farm, and the Crawfords moved to Portland.

In the city, Reuben Crawford found that his shipbuilding skills were not only in demand but also highly respected. In a 1903 profile, the New Age reported that "as a caulker, he stands second to none in the city, and is always sure of work if there is any being done." He held an office in the Caulkers Union and christened two ships, a steamer and a barge commissioned by the Clatskanie Transportation Company. His job title was "dean of the Willamette River Caulkers." Crawford retired in 1913 at the age of eighty-five. He celebrated his eighty-sixth birthday by returning to the shipyards and visiting with Captain James Shaver, founder of the Shaver Transportation Company and the best-known shipbuilder in Portland. 

When not working, Crawford dedicated his time to organizing. He was a founding member and first vice president of the Portland Colored Immigration Society in 1879, working to bring more Black families to Portland, and he represented the Bedrock Republican Club at the 1894 Oregon Republican Convention.  A devout person, Crawford was the founding Deacon of Mt. Olivet Baptist Church in 1897. He was active in both the church and the New Northwest Lodge for the rest of his life. 

Reuben Crawford died on April 9, 1918. His funeral was held at Mt. Olivet Baptist Church under the auspices of the Odd Fellows, and he was buried at Lone Fir Cemetery. Crawford's grave remained unmarked until 2020, when the Peninsula Odd Fellows lodge in North Portland erected a headstone with this inscription: Reuben Crawford PNF "The Dean of Ship Caulkers." PNF, which stands for Past Noble Father, is the highest rank that can be achieved in a lodge of the Grand United Order of Odd Fellows.

Reuben Crawford's legacy was continued by his daughter, Harriet "Hattie" Redmond. When she was elected Most Worthy Governor of Golden West Lodge in 1903, her father was her Vice Most Worthy Governor. Redmond was also secretary of the Colored Women's Equal Suffrage League in 1912 and the founding vice president of the Colored Women's Republican Club in 1914.