Although slavery was declared illegal in 1844 by the Oregon Provisional Government, many people brought slaves with them across the Oregon Trail. Due to the length and difficulty of the journey, most slave owners brought only a few slaves West -- often a single longtime family servant and generally no more than a family of slaves, or at least those members deemed able to survive the trip.
The ban on slavery in the Oregon Country had nothing to do with abolitionist leanings. In fact, the opposite was true: slavery was outlawed as a means of keeping the black population in Oregon to a minimum. Owning slaves was widely tolerated in the Northwest, and while some slaves successfully sued for their freedom or the freedom of loved ones, no whites were ever forced to free their slaves upon entering the Oregon Country after 1844. However, some did follow through on promises to free their slaves upon arriving in Oregon, and a small population of free blacks gradually became established in the Pacific Northwest.
Slaves were too valuable for many owners to willingly give them up. Nathaniel Ford, an emigrant of 1844, brought with him three slaves: Robin and Polly Holmes, and their daughter Mary Jane. Ford had promised to free the Holmes family after he had established himself in Oregon, but in 1850 he agreed to free only Robin, Polly, and their infant son -- the Fords kept three other children, including Mary Jane. After a long court battle, the other children were freed by order of the court in 1853. The judge cited the fact that slavery was illegal in the Oregon Territory as the reason for his decision. Although she had been freed, Mary Jane Holmes continued to live with the Fords until her marriage in 1857, and her husband had to pay Nathaniel Ford $750 for permission to marry her.
Not all relationships between slave and master were so antagonistic. In 1849, Rose Jackson willingly traveled the Oregon Trail inside a box in the back of a wagon, coming out only at night to stretch and get some fresh air. Her owners credited her work as a laundress with helping the family survive their first winter in Oregon.
Racism became more widespread and severe along the West Coast in the years leading up to the Civil War. The California legislature almost passed exclusion laws twice, prompting many free blacks to head north to British Columbia. Some slaves still held in the old Oregon Country escaped north, as well. In 1860, a boy held by James Tilton, Surveyor General of the Washington Territory, escaped to Victoria, BC, and was protected by the British. Nothing came of Tilton's protests to the Secretary of State in Washington, DC.
Pro-slavery groups agitated repeatedly to form a new federal Territory -- and eventually a new slave state -- out of what is now southwestern Oregon and northern California. Significant gold strikes in that area in the early 1850s lent some weight to the forces backing this plan, but the first effort in 1854 was thwarted when California refused to cede any of its land. A second attempt in 1857 also failed.
Also in 1857, a bill was proposed in the Territorial Legislature to protect the property of slave owners. While ostensibly intended to protect the interests of slave owners passing through the Territory, it was almost certainly intended to legalize slavery by allowing slave owners to keep their slaves after moving to the Oregon Territory. Forces opposed to the bill defeated it by arguing that it would grant special rights to slave owners which were not enjoyed by the citizens of Oregon.
With statehood imminent in 1858, Oregonians elected their first slate of state officers and legislators. Pro-slavery forces made an excellent showing at the polls, as Governor "Honest John" Whiteaker and other officials elected that year were well known for their views on blacks. Still, Governor Whiteaker was judged to have ably guided the newly minted State of Oregon through the Civil War. One of his contemporaries, Judge Matthew Deady, said of him, "Old Whit ... Wrong in the head in politics, he is honest and right in the heart."
Oregon's early racial politics were dominated by a wish to simply be free of the problem altogether by not allowing blacks to settle here. There was a degree of consensus between the pro-slavery and abolitionist sides to ignore the problem and hope it stayed in the East. Ignoring the problem, however, gave tacit approval to scofflaws who continued to hold slaves after settling in Oregon.