John Arnot Mathews was born in Elmira, New York in 1824. He learned the mercantile business from his father, and left for Pennsylvania to become a merchant in 1845. He came to Winona in 1855, and established his business on Front Street, as a real estate and loan office. He earned the confidence of the town citizens, being elected mayor for four terms. He was a stockholder and director of the Winona & Southwestern Railroad, although he did not advocate the use of public funds to support the railroads. He was called “one of the most popular men of Winona, a safe and substantial business man, a true friend.”
Mathews endorsed the notes of the Mahaiwe Bank for a short time in 1856, in order to create a circulating medium for his locale.