James “Jim” Anderson was a brother to William “Bloody Bill” Anderson, the famous Missouri Bushwhacker and Confederate guerilla in the Civil War.

James Monroe Anderson was born to Willam C. and Martha Thomason Anderson in Randolph County, Missouri in 1842. In 1850, his father followed the California Goldrush but later came back empty-handed. In about 1857, the family moved to Kansas, where they settled near the Bluff Creek Crossing on the old Santa Fe Trail in Lyon County. This area was made up largely of Free State residents and the Andersons were pro-slavery, so, at once, they found themselves at odds with their neighbors.

The eldest of seven children, 18-year-old Bill took jobs in the area and purchased land next to his father’s property. He then began to work for wagon trains making their way to and from Santa Fe, New Mexico. However, he and his brother Jim, along with several cousins, became horse thieves

Mrs. Anderson was killed by lightning in June 1860. Two years later, her husband, William got into an altercation with a neighbor, A.I. Baker, on May 7, 1862, and was killed. Afterward, Bill and Jim Anderson fled to Missouri, later sending a man to retrieve their three sisters who were placed with friends in Missouri. A few months later, the boys went back to Kansas and killed Baker.

The embittered brothers then formed a company of Confederate Missouri Partisan Rangers and raided Union Forces and sympathizers through the summer and fall of 1862. In the Spring of 1863, they joined William Quantrill’s guerrilla band.

In August 1863, shortly after Union General Thomas Ewing issued the infamous Order No. 11, the Andersons’ three sisters Josephine, Mary Ellen, and Martha, along with some other female relatives of guerrillas, were arrested and held by Union forces in Kansas City. On August 13th, the building collapsed, killing 15-year-old Josephine and crippling 10-year-old Martha. In retaliation, Quantrill’s band of partisans, along with Bill and Jim Anderson, sacked Lawrence, Kansas on August 21, in a brutal reprisal. From that day forward, throughout the rest of the war, the Andersons killed, and often scalped and mutilated every Federal Soldier they could get their hands on.

Jim’s brother, “Bloody Bill” Anderson was killed on October 27, 1864, but Jim continued to fight for the Confederate cause. When the war was over, he surrendered in Kentucky and for unknown reasons was sent to prison in Alton, Illinois. He was released at the end of 1865, after which, he joined the James-Younger Gang. In April 1866, Jim teamed up with Jesse James and killed a man named Ike Flannery in order to steal his recent inheritance of several thousand dollars.

Afterward, Jim made his way to Sherman, Texas, taking his two sisters with him. There, he married Mary E. “Mollie” Erwin Smith on October 21, 1868. In the meantime, Jim had made an enemy out of George W. Shepherd, who was a former member of Quantrill’s guerrillas and a member of the James-Younger Gang. Shepherd was the uncle of Ike Flannery, who Jim had killed in Missouri in 1866. On May 5, 1871, Shepherd tracked down Jim Anderson to Austin, Texas, where he slit his throat on the lawn of the State Capitol building.

Jim’s wife, Mollie, was pregnant at the time and gave birth to a daughter, Jimmie Maude Anderson, on August 21, 1871.

© Kathy Alexander/Legends of America, updated May 2022.

Also See:

James-Younger Gang

Old West Scoundrels

Outlaws on the Frontier

Outlaws & Scoundrels Photo Gallery