Dr. Sylvester B. Prentiss was born at Chester, Massachusetts on May 4, 1817. He was educated in the common schools and academies of Massachusetts and New York. In the fall of 1836 he left home and alternately taught school and studied medicine until he received his diploma in 1844. He began his practice in Coventry, New York. In 1846, his health being impaired, he moved to Jackson, Georgia, where he engaged in medical practice.

Anticipating the struggle between the North and South, he moved to Kansas and arrived in Lawrence on May 3, 1855. After making a tour of the territory, he selected Lawrence as his home. He settled upon the quarter section just northwest of town, where he lived for many years, enduring all the hardships and privations of pioneer life.

As an active Free State man, Dr. Prentiss was often beset by border ruffians and had some thrilling adventures in connection with early troubles. When the Free State Hotel was burned May 21, 1856, the ruffians surrounded his house and demanded whatever arms they might have. He and his wife presented guns at the windows and threatened to use them, and the marauders fled. His services as surgeon were often called for by both sides.

When Jones, a Free State man, was shot on the Wakarusa, it was Dr. Prentiss who was called to remove the bullet that killed him. (The bullet was later placed at the Kansas Historical Society). It was also he who, on his way back to town, found the dead body of Stewart, who had been shot during the doctor's absence. He loaded the body into his buggy and brought it into town.

He was also at Franklin with the company that went to capture the Ruffian Stronghold. In his own words--"I suppose the company thought it was a small affair, but to me it was quite exciting. I went to take care of the wounded, not expecting to have any, but we did. The company of ruffians were entrenched in a log house, through the cracks of which they poured a murderous fire into the ranks of the attacking party, killing one and wounding many. We began to think that we should have to give it up, when a load of hay was fired and run against the house, which drove them out."

When Colonel Titus was wounded, Dr. Prentiss dressed the wound. When 101 Free State men were in prison in Lecompton in 1856, he was called upon to be their physician. His office and drug store, located in the Eldridge Hotel, were destroyed in Quantrill's Raid, but he was moving around among the wounded before Quantrill had left town. Dr. Prentiss himself had a narrow escape. Hearing shots [while at home], he took his gun and started for town but was met by Mr. Gates, a neighbor, who was being pursued by two of Quantrill's men. Mr. Gates called "For heaven's sake, doctor, go back, it isn't war but murder." He turned his horse and rode back with Mr. Gates till their roads parted. Both raiders followed Mr. Gates and killed him in his yard, but Dr. Prentiss reached home safely. He came into town as the raiders were leaving.

He remained on his claim a number of years, building a comfortable home, planting trees all about, until the "Prentiss Place" became one of the most charming spots of Lawrence. After a time, his practice so increased that he moved into town to be nearer his work.

While he was only a private citizen and preferred to be only that, he was always interested in public affairs. He was emphatically a public-spirited man, interested in all questions which concerned the people. On the slavery question, and later on the temperance question, he was always decided and pronounced, and at the same time discreet and charitable. He took great interest in education matters, and in 1857 was "chairman of the citizen's committee on schools," which was as near a school board as they could get in the chaotic conditions of the times. Under this committee, the "Quincy High School" was carried on with success.

Without wanting office, he held numerous positions of responsibility. In 1855, he was commissioned surgeon general of Kansas volunteers; in 1857, surgeon of the Kansas militia. During the Civil War, he served as commissioner to examine applicants for the office of surgeon in Kansas regiments. He was the first president of the Kansas Medical Society, also first president of the Douglas County Medical Society.

Dr. Prentiss was married three times. He married Miss Louisa Brooks on October 25, 1839, at Norwich, New York. She died leaving two children, Joseph Lyman and Louisa Brooks. On April 14, 1847, he married Mary N. Converse at Coventry, New York. Mrs. Mary Converse Prentiss came to Lawrence with her children in October of 1855, six months after Dr. Prentiss arrived. She died May 22, 1865, leaving two children, Ella Allis and Frank. Dr. Prentiss married Annie J. Soule on June 21, 1866. They had two children, Hattie May (who died in infancy) and Charles Addison.