Together with his father, Dr. Benjamin Davenport, Timothy Woodbridge (T.W.) Davenport set forth across the American continent in the spring of 1850. Because of misguided leadership of one of the members of their team, the Davenports decided to take an overland route from Ohio instead of opting for the quicker, water route along the Ohio and Mississippi Rivers to Missouri. By the time they reached Missouri, the team was months behind the rest of the pioneers on the Oregon Trail and their oxen were already showing signs of wear. This late start may have been a blessing in disguise. As the Davenports proceeded across the Great Plains they heard of the massive cholera epidemic plaguing travelers that went before them. Before they reached the rigorous Rockies, the Davenports wisely decided to return to Newark, Missouri where they would wait out the winter. In Missouri Benjamin set up a medical practice for the winter and was able to purchase a new team of oxen for the trip. In the spring of 1851 the Davenport family once again set out across the plains, this time reaching Oregon Territory in the fall of that year and settling upon a 320-acre donation claim in the Waldo Hills of the upper Willamette Valley.

The first member of the Davenport family had arrived in America from England prior to 1640, originally settling in Dorchester, Massachusetts. The family remained in the Northeast for several generations. Benjamin Davenport, father of Timothy Woodbridge, was born in Columbia County, New York in 1799, the thirteenth child of Jonathan Davenport. Jonathan Davenport died when Benjamin was young. One of the few memories that Benjamin had of his father was of Jonathan lacing up his boots and exclaiming in pain. Jonathan removed his boots and socks to find a red pimple on his foot. Jonathan popped the pimple and died soon thereafter because of an infection in his foot. While the veracity of this story is hard to determine, it may have been a spark for young Benjamin to embark upon a medical career.

Benjamin Davenport left the Northeast for a while as young man, traveling to the South. Benjamin spent five years in the South, primarily in Kentucky and Louisiana. Despite a lack of formal education, Benjamin began practicing medicine. Relying on his quick wits and sound judgment, Davenport studied in his spare time and earned a reputation as a fair physician. While in the South, Benjamin objected to slavery, and he passed this sentiment onto T.W. When he returned to the North he would become an anti-slavery Whig and his home would eventually become a stop on the Underground Railroad. Upon his immediate return he resumed his medical studies with more rigor, eventually graduating from Pittsfield Medical College in Pittsfield, Massachusetts in 1826.

In 1825 Benjamin Davenport married Sarah R. Gott. Sarah had been born in 1803 to Story Gott, a wealthy landowner from Columbia County, New York. Story Gott was a popular man, known for his generosity and Epicurean tastes, as well as his distinguished service for the patriot cause during the American Revolution.

Timothy Woodbridge Davenport was born to Benjamin and Sarah on July 30, 1826 on a farm in Columbia County, New York. He was baptized in the Presbyterian faith and named after a blind minister, Timothy Woodbridge. The twenty-six letters of this name seemed too cumbersome for such a young boy so he earned the nickname T.W. His early years were spent at his maternal grandfather’s farm while his father continued with his medical education in New York.

Benjamin remained in New York, practicing medicine, until 1830. In the spring of that year his second son, Joseph, was born. That summer, in the first of series of moves westward, Benjamin moved his family and practice to Pennsylvania. He remained in Pennsylvania for five years before moving to Ohio where he jumped from town to town, finally taking up residence in Homer, Ohio.

While in Ohio, Dr. Davenport worked as an abolitionist helping slaves escape northward as part of the Underground Railroad. This period represented one of growth for T.W. as well. T.W. received the benefits of education, both in public schools and with private tutors. His studies ranged from classic Greek to Algebra and Geometry, which were beyond the normal curriculum for the time. The emphasis placed on education at an early age is clear from T.W.’s eloquent writing style. In 1845 T.W. went to Illinois as a schoolteacher and remained for two school years.

After two years as a schoolteacher in Illinois, T.W. decided to follow his father’s example and study medicine. T.W., however, was not as interested in the medical profession as his father and after one year at Sterling Medical College he returned to teaching in Woodstock, Ohio, though without much interest. When his father proposed a move across the country, T.W. jumped at the chance, planning to become a surveyor in Oregon.

The first years in Oregon were busy ones for the Davenport family. T.W. engaged in surveying and farming, but as his son Homer noted he was always a “politically minded farmer.” T.W. married his second cousin, Flora Geer, a gifted artist, and daughter of a prominent local family in 1854. In 1855 father and son, spurred by their abolitionist beliefs, helped organize the fledgling Republican Party in Oregon. This involvement led to the beginning of a political path for T.W. who would be elected to the first Republican state nominating conventions in 1858 and 1859.

While things seemed to be on an upswing for T.W. in these early years, tragedy struck in February 1857 with the death of Dr. Benjamin Davenport at the age of fifty-seven.

The outbreak of the Civil War in 1861 thrust the country into turmoil, though Oregon was able to stay out of the path of destruction. T.W.’s youngest brother Benjamin Franklin Davenport joined the Union cause, serving three years in Company C of the 1st Oregon Infantry. Being too old for military service, T.W. was asked by the Superintendent of Indian Affairs, William H. Rector, to serve as Indian Agent of the Umatilla Agency in September 1862.

T.W. entered a system fraught with corruption and broken promises. Many people gave lip service to the “civilizing” mission of the reservation system, but few people believed it was possible to “reform” the Native American population. T.W. was an exception. He honestly believed that he could make a difference, so he set out in October 1862 to the Umatilla Reservation in northeastern Oregon brimming with confidence.

The first action taken by T.W. upon arriving at the reservation was to appoint a man named Mr. Pinto to the position of schoolteacher. By doing so, T.W. amended a promise broken by his predecessor. This action upset the reservation doctor who wanted his wife, despite her lack of qualifications, to fill the vacancy. The reservation doctor resigned in protest, but told the reservation Indians that he had been fired, which angered the Indians. While T.W. managed to placate the outraged tribal leaders this incident illustrates how T.W.’s good intentions were met with resistance from the beginning of his term. T.W. was constantly challenged by Indians who, understandably, refused to move onto the reservation and by Army officers who expressed hatred for Indians. While he would write a fond reminiscence about his experience for the Oregon Historical Quarterly forty years later, T.W.’s term was not as successful as he hoped and he returned to the Willamette Valley in 1863 after less than a year of service.

The next few years would be ones of growing political success for T.W. He was elected Marion County surveyor in 1864 and reelected in 1866. In 1868 he was elected to the state legislature and reelected in 1870. He was nominated again in 1872, but declined the position. As always, these years of success were mixed in their blessings. While his political success grew, personal tragedy struck.

In November, 1870 T.W.’s wife Flora was struck with smallpox and died. The couple had produced four children. Their daughter Olive had died at age four and their son John did not live past infancy. After his wife’s death, T.W. became the single father of daughter Orla and his three-year-old son, Homer. That winter was a hard one for the Davenport family as T.W. grieved for his wife and, with the aid of his mother, cared for two children who were recovering from smallpox as well. The intense rains added to the isolation, darkening the already gloomy mood. Young Homer, trapped by rain and illness, spent his time drawing with intense vigor.

T.W. married Nancy Elizabeth Gilmour (Lizzie) in October 1872. Clyde was born in 1873, Adelaide (Adda) in 1875, Alice in 1878, Georgia in 1880, and May Delle in 1885. T.W.’s political career took some time to get back on track. He ran for Congress in 1874 on the Independent ticket, but his bid was unsuccessful. In 1882 he was elected to a term in the state senate and in 1895 Governor William P. Lord appointed him to a four-year term as the state land commissioner. Throughout this time T.W. continued to write political and historical essays on subjects ranging from the origin of abolitionist sentiment in Oregon to the support of William Jennings Bryan and the Populist cause.

Homer Davenport seemed to be a perfect blend of his parents. He had his father’s political sensibilities and his mother’s artistic talent. These traits combined to form a political cartoonist with a touch of genius. In fact, his mother actively tried to bear a genius. Following the advice of a eugenicist, Flora abstained from meat and salt during pregnancy and attempted to get exercise and fresh air. The key element in this design lay with the conception. The child must be conceived during daylight hours, preferably outdoors.

Homer’s artistic genius came not from art schools or scholarly study, but rather from a combination of an active imagination and a keen eye for detail. T.W. lovingly recalled the hours Homer would spend watching the interactions of barnyard animals and then recreating their actions. As he grew he would examine art books and nearby galleries, but he would not imitate the work he saw, preferring to use his imagination as a muse.

As a young man Homer grew restless. He worked at the family store for a while without much interest. Homer left home as a young man drifting from job to job, working as a railroad fireman, a jockey, and even a circus clown. His drifting led him to Portland where he landed a position as an artist for the Portland Mercury.

While in the employ of the Mercury, Homer was sent to New Orleans to make some drawings of the Dempsey-Fitzsimmons boxing match. While on the train he drew some pictures of an African-American minister preaching on a train in Texas. He sent these sketches to his father, who was so impressed with them that he sent them on to cousins in Chicago. As legend has it, these relatives opened the drawings while entertaining the head of the art department for the San Francisco Examiner. Homer was quickly offered a position at the larger newspaper, and he quickly accepted, beginning work in 1892.

The circulation of the Examiner spread Homer’s cartoons to a larger audience. Homer soon gained a reputation for bold cartoons that were not afraid to tackle any issue, including the political machine that ran the city. These cartoons soon caught the attention of William Randolph Hearst. When Hearst purchased the New York Journal in 1895, he wooed Homer away from San Francisco and into the national spotlight.

At the New York Journal Homer increased his attacks on corruption in politics, targeting the big trusts and the McKinley campaign for being beholden to big business. One figure that Homer attacked with particular vehemence was McKinley’s campaign manager “Dollar” Mark Hanna. Davenport portrayed Hanna as grossly oversized, wearing a suit covered in dollar signs and smoking a large cigar. These cartoons enraged his critics so much that they attempted to pass an anti-cartoon bill through the New York legislature in 1897. Fortunately for Davenport public opinion was on his side and the bill was defeated.

Homer Davenport’s political cartoons opened doors for him around the world. He visited the British Parliament, becoming one of the first American cartoonists to watch the assembly. With the aid of friend Theodore Roosevelt, Homer traveled to the Ottoman Empire, returning with the first purebred Arabian horses in America. These horses became his passion. Despite being the highest paid cartoonist in the nation, he preferred to remain on his New Jersey farm with his children and his beloved horses.

Homer’s life was cut short in 1912 when he died of pneumonia after covering the sinking of the Titanic. Hearst, to honor his beloved cartoonist, had his body sent back to Silverton to lay next to his father. T.W. died only a year before Homer, in 1911.