Pinkerton, McClellan was sleek, handsome, and dashing, and had led something of a charmed life. Born in Philadelphia in 1826, McClellan had entered the University of Pennsylvania at age thirteen, then transferred to West Point two years later, graduating second in his class. Upon leaving the academy, he served with distinction in the Mexican-American War, even performing reconnaissance missions for Lt. Gen. Winfield Scott, a close family friend. Following the war, McClellan joined Randolph Marcy’s expedition to discover the sources of the Red River, only to find upon his return that all the members of the expedition had been given up for dead. The following year, he put his engineering skills to work for Secretary of War Jefferson Davis, exploring possible routes for the transcontinental railroad. In 1855, at the height of the Crimean War, McClellan was dispatched as an official observer of the European armies, later producing a manual on cavalry tactics and a design for a “McClellan saddle,” which became standard U.S. Army issue.
When Pinkerton met him in 1857, McClellan had resigned his military commission, capitalizing on his engineering and railroad experience to secure a lucrative position with the Illinois Central. Though McClellan was seven years younger than Pinkerton, his remarkable catalog of achievements made a forceful impression on the detective, who adopted the young officer as a mentor and role model. Soon enough, their relationship would take a new shape on the battlefields of the Civil War, amid lasting controversy. To the end of his life, Pinkerton would be one of McClellan’s staunchest supporters, declaring himself “proud and honored in ranking him foremost among my invaluable friends.” In terms of political beliefs, however, it is difficult to understand how the seeds of that bond were sown so deeply during their early association in Illinois. Many of McClellan’s views would have struck Pinkerton as shortsighted and timid. McClellan had no particular sympathy for the institution of slavery, and he hoped to improve the condition of “those poor blacks,” but there were clear limits to his resolve. As he told his wife, “I will not fight for the abolitionists.” Even so, Pinkerton embraced him as a kindred spirit. “From its earliest incipiency,” the detective wrote, his working relations with McClellan had been of “the most agreeable and amicable nature.”
Pinkerton was oddly silent about another of his Illinois Central colleagues of this period. Like Pinkerton, Abraham Lincoln was on retainer with the railroad during these years, and the career of the circuit-riding lawyer—like the detective’s—was inextricably linked to the fortunes of the company. Having returned to practice law in Springfield after serving a term in the U.S. House of Representatives, Lincoln often found himself engaged in the legal issues arising from the rapid spread of the railroads across the state, and by the mid-1850s the bulk of his practice was devoted to railroad law.
George McClellan recalled crossing paths with Lincoln on many occasions during these years. “More than once I have been with him in out-of-the-way county-seats where some important case was being tried,” wrote McClellan, “and, in the lack of sleeping accommodations, have spent the night in front of a stove listening to the unceasing flow of anecdotes from his lips. He was never at a loss, and I could never quite make up my mind how many of them he had really heard before, and how many he invented on the spur of the moment. His stories were seldom refined, but were always to the point.”
Whatever his personal feelings may have been, McClellan made his political views clear during the fateful election campaign of 1858, when Lincoln, as the candidate of the newly formed Republican party, challenged incumbent Stephen Douglas for his seat in the U.S. Senate. McClellan and many other Illinois Central men threw their support behind
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