James Bosler was born on April 4, 1833 to Abraham and Eliza Herman Bosler in Silver Spring, Cumberland County, Pennsylvania. He attended the Cumberland Academy at New Kingston, Pennsylvania before entering the nearby Dickinson College as a member of the class of 1854 along with his older brother John Herman Bosler. Neither brother finished their degrees and James Bosler withdrew from the College during his junior year and moved west.
From 1852 to 1854, Bosler taught school in Moultrie, Columbiana County, Ohio, where he also built his first store. After the store was destroyed by fire, Bosler moved to Virginia. In Wheeling, Virginia, he was admitted to the Bar, but the life of a lawyer did not suit him. Moving further west in 1855, Bosler partnered with Charles E. Hedges in Sioux City, Iowa in the real estate business. Together they established the Sioux City Bank under the name Bosler & Hedges. Bosler soon expanded his business interests into the growing cattle market, where he made his fortune. He served a brief term in the Iowa State Legislature, before returning to Carlisle in 1866.
In 1860 he had married married Helen Beltzhoover of Boiling Springs, Pennsylvania and the couple had two boys and two girls. Bosler remained a strong supporter of Dickinson College throughout his life. In 1883, he pledged $10,000 to endow a faculty chair, which his widow carried out after his death on December 17, 1883. Rather than merely fulfill the original pledge, Helen Bosler donated nearly seven times that amount to erect a new library hall for the College. She insisted that only the most durable materials, least liable to fire, be used in the construction, instead of constructing a larger building out of cheaper materials. The James W. Bosler Memorial Hall was completed in 1886, and housed the College’s library until 1967. Today Bosler Hall is home to the modern language departments.