It is thought that this is Ella DeSombre (1902-1987) and August Pfeiffer's (1901-1960) wedding photo. The wedding took place in Swanville, Todd County, Minnesota. They were married 06/03/1930. (The man on the left is unidentified.)
Carl DeSombre (1859-1929) owned 3 properties in Sheboygan. The photo is of the South East corner of 12th Street and Michigan Avenue. The building on the corner housed The North Side Drug Co. and had 5 apartments upstairs with a shared bathroom. Carl also owned the house to the east of the store (left side of photo). He lived in the house until his son William DeSombre built the home to the south of the store (right side of the photo). His children Ella and George lived in the house after his death in 1929.
From Bayside Cemetery in Sevastopol, WI just outside of Sturgeon Bay. Quite a large monument and one of the best I have found. Lying in front of the monument from left to right are Carl DeSombre, Augusta DeSombre and Lydia Heimbecher.
William DeSombre (1889-1964) took an active roll in politics. He ran for alderman on at least two occasions in 1925 and 1935. He was the chairman of the Central Labor Council and chairman of the Sheboygan Socialist Campaign Committee. It appears that he was unsuccessful in becoming an alderman.
The ad for sheriff is from The Sheboygan Press dated 09/01/1922.
The article about his candidacy for alderman is from The Sheboygan Press dated 03/21/1935.