James Oswald Swinney was born in Lynchburg, Virginia, on March 20, 1830, to William D. Swinney and Lucy Ann Jones. His father was a wealthy tobacco dealer who eventually owned at least 86 slaves and $240,000 in property. The family moved to Howard County, Missouri, in the fall of 1832, and “Oswald” (as his family called him) enrolled at St. Charles College in 1843. While he was there, his mother urged him to attend Bible classes and avoid “bad habits, extravagances or anything else not praiseworthy.” Conditioned to a life of privilege, however, Oswald complained bitterly about the school and frequently ran into debt. In response, his father scolded him for failing to “appreciate the value of money. You do not know what it costs to get it & spend it for things of no value.”

Swinney enrolled at Yale University in 1849 and remained there for the next three years. During the 1851-52 academic year, he transferred to the University of Virginia, where he studied moral philosophy, natural philosophy, and chemistry. He married Maria Caroline Savage in Mason County, Kentucky, on November 10, 1852, and the couple settled in Howard County, Missouri. They had two children: Mary Ann, born around 1855; and William Daniel, who was born on June 5, 1858, and died of scarlet fever on November 5, 1863. Swinney purchased the local Hazel Ridge plantation in 1853, and the following year he formed a partnership “for the purpose of engaging in the Tobacco business.”

Swinney followed his father into the Whig Party, and in 1852, he helped organize a public dinner honoring Whig Congressman John G. Miller. Then, in 1855, he attended a pro-slavery meeting in Glasgow, Missouri. The crowd vowed to extend slavery into the neighboring Kansas Territory, sending “emigrants there who…will defend our common interest.” Swinney joined a local committee to put these plans into action. A year later, at another “Kansas Meeting,” he agreed to collect the names of “all the volunteers who went to Kansas from Howard County” and calculate “the amount of money to be allowed to each volunteer.”

Swinney remained loyal to the Union during the Civil War, but he initially tried to remain out of the conflict. By 1862, however, Union forces occupied the family’s Sylvan Villa and Hazel Ridge plantations. As Maria reported, “Oswald was compelled to go into the militia or leave home.” On October 3, 1862, he received a commission as a 2nd lieutenant in the 46th Enrolled Missouri Militia Regiment. In December, he was promoted to captain and placed on the staff of General Thomas Bartholow. He resigned his commission on March 20, 1863, and officials declared him exempt from future militia service.

Swinney’s father died in 1863, and he inherited roughly half of the estate, including “a large number of slaves.” Later that year, with slavery beginning to crumble in Missouri, Swinney offered the African Americans their freedom “under certain instructions.” Swinney would pay for them to leave the state, or they could remain on Swinney’s property as hired workers. Swinney gave his own slaves a similar choice, proposing to “liberate and emancipate all the slaves I own who may choose to emigrate from the state of Missouri.” He planned to “hold” the men and women who refused to leave “with the same control I now have over them as slaves for the term of five years,” at which point he would set them free.

The Civil War wrought economic devastation across much of the South. Because of his inheritance, however, Swinney emerged from the war much wealthier than before. By 1870, he and his wife owned more than $315,000 in property. He used this wealth to build Eglantine Castle, an elegant seventeen-room mansion, and to establish Pritchett Institute, a small college in Glasgow, Missouri. Swinney opened his home to friends and relatives, serving as the guardian for his niece, Berenice Morrison, and his granddaughter, Berenice Scarritt. The latter embroiled the family in a high-profile custody dispute. Swinney’s daughter Mary Anne died on August 28, 1876, and left her one-year-old daughter in Swinney’s care. The child’s father, Edward Scarritt, agreed to let her stay with Swinney until she turned 10. In January 1882, however, he filed a petition with the state Supreme Court, determined to regain custody of his daughter. The justices ruled in Scarritt’s favor, observing that a father “cannot irrevocably divest himself of…the custody and charge of his child.” Even so, they praised the Swinneys for their “amiability, culture, and deeds of labor and love.”

In the 1870s, Maria wrote, “Oswald entered into some mining speculations and lost all he had.” He invested his fortune in the Catlin Coal Mine in Illinois, the Juniper Silver Mine in Nevada, and the La Alba Silver Mine in Mexico. He overextended himself, however, and when these speculations failed, he fell deeply in debt. He was forced to leave Eglantine Castle and sell most of his property to his wealthy niece, Berenice Morrison. Undeterred, Swinney continued to seek financial success, reviving his tobacco business and purchasing a homestead a Colorado.

Eventually, Swinney vowed to “have no other business than preach the Gospel of Christ to my dying day.” He had converted to Methodism in 1855 and had become a circuit-riding minister in 1863. He had left the ministry after inheriting his fortune, and he later confessed that “nothing but sin and sorrow has come to me since I ceased to do that work.” Chastened by financial collapse, Swinney renewed his faith in the late 1870s. He described himself as a “Methodist Minister” in 1880 and published at least three religious tracts between 1879 and 1884. In 1894, he served on the Committee on Temperance at the Methodist Church’s annual state convention. The following year, he attended a Methodist district conference, and a local writer observed that he was “known by every one here” and “still very active in church work.”

By the 1880s, however, Swinney’s health had begun to decline. In 1882, the state’s Supreme Court justices described him as “in the decline of life, with health, never robust, much shattered and broken by unutterable sorrow [after losing his only daughter].” In the 1890s, one writer described him as a “total physical wreck,” observing that he suffered from “bladder, urinary and prostatic troubles.” He died in Glasgow on October 6, 1899, “from the effects of an overdose of laudanum taken through mistake.” Editors praised him as “one of the most influential and highly respected citizens of Howard County” and “one of the leading pastors of northwestern Missouri.” His funeral took place in the Glasgow Methodist Church, and he was buried in Washington Cemetery.