There are two stories pertaining to how Abraham Lincoln and proprietor and editor John G. Nicolay met. Thomas Hall Shastid, grandson of John Greene Shastid tells the story that while Lincoln was in Pittsfield, he ran into John Greene Shastid telling him that he needed a good printer. John took him to the office of the Free Press and introduced him to Nicolay.
In 1894 Nicolay granted an interview that went viral in the national newspapers. He was asked about the first time he met Lincoln. Nicolay said that he had been actively serving on a political committee in Pittsfield in the year 1856. That year John C. Fremont was running for president on the Republican ticket and Abraham Lincoln and Lyman Trumbull were canvassing the state of Illinois for votes. It was a large district Lincoln and Trumbull agreed not to appear together in the same location.
Nicolay went on to say that the committee did not know who was coming to Pittsfield so they advertised that both Lincoln and Trumbull would be there. It wasn’t a total lie, one of the men would show at the scheduled date and time. When the time came both Lincoln and Trumbull showed up in Pittsfield. The crowds were huge as the two men gave speeches well into the night. Nicolay stated that he was introduced to Lincoln late that evening.