Known Activities
Leadership of the Pinkerton Agency
Robert Allan Pinkerton served as principal of the Eastern branch of the Pinkerton Detective Agency, while his brother William Pinkerton managed western United States operations. (Source: bisbee_daily_review_1907-08-24_image8) By 1907, the brothers shared oversight of the agency, which reportedly employed over 1,500 people, with branches in major cities across the United States and Canada and agents operating in Europe as well. (Source: litalia_1907-09-14_image5)
Education
According to the News-Democrat, Robert Allan Pinkerton received his education at Notre Dame University in Indiana. (Source: news_democrat_1907-08-17_image1)
Methods and Reputation
According to the Bisbee Daily Review, Robert Allan Pinkerton was known among contemporaries as "the Chesterfield of detectives," a characterization that speaks to a certain polished, methodical quality in his professional manner. He was particularly noted for his skill in scheming and laying traps for criminals, rather than relying solely on pursuing and hounding them. He also worked on several major crimes in the Southwest. (Source: bisbee_daily_review_1907-08-24_image8)
Labor Confrontations
The agency under Pinkerton family leadership was involved in some of the most contentious labor disputes of the Progressive Era. According to the L'Italia account, in 1894 Pinkerton Agency forces engaged striking workers — described as being of various nationalities — at Carnegie facilities in Pittsburgh. The account notes that strikers had armed themselves with two Maxim cannons, and the confrontation resulted in what the source characterizes as bloody combat ending in the agency's victory. (Source: litalia_1907-09-14_image5) The precise role of Robert Allan Pinkerton versus William in directing these operations is not specified in the available source.
The Dundee Connection
Robert Allan Pinkerton was born in Dundee, Illinois in 1848, making his connection to that community a matter of personal biography rather than merely inherited family history. (Source: bisbee_daily_review_1907-08-24_image8) The L'Italia obituary account further situates Robert's legacy within his father Allan Pinkerton's origins in Dundee, Illinois. Allan Pinkerton — described in the Bisbee Daily Review as a Scotchman — emigrated to Dundee approximately 50 years before Robert's 1907 death, placing his arrival around 1857, settling in what was then described as a small frontier town roughly 30 miles from Chicago, reportedly infested with horse thieves, cattle rustlers, and counterfeiters. Allan Pinkerton was originally a cooper (barrel maker) by trade; his reputation for combating local criminals led to his election as sheriff of Dundee before he eventually moved to Chicago and established the detective agency that Robert and William would later inherit and expand. (Source: litalia_1907-09-14_image5)
Timeline
| Date | Event |
|---|---|
| 1848 | Robert Allan Pinkerton born in Dundee, Illinois (Source: bisbee_daily_review_1907-08-24_image8; news_democrat_1907-08-17_image1) |
| c. 1857 |