William Middlebrook was born in Lindsley, Steuben Co. New York on July 22, 1864. He received his early education in Lindsley and then went on to attend Allen’s Business College in Elmira, New York. Middlebrook worked for a time as a bookkeeper in New York before coming to Manistique in the spring of 1886. Here, Middlebrook found employment with the Weston Lumber Company and was placed in charge of the Clothing and Dry Goods Department of the company’s general store on Deer Street. He married Dora R. James in a ceremony at Manistique on June 2, 1887.