mayor Wentworth instituted the use of chain gangs of prisoners in the city as laborers. In July 1857, while serving as mayor of Chicago, Wentworth was charged with assaulting an attorney named Charles Cameron, who was attempting to communicate with his incarcerated client. Cameron testified that Wentworth "seized him by the coat collar and shirt bosom" and forcibly removed him from the prison, alleging that he had resisted officers. Wentworth, after requesting the case be delayed twice, refused to appear in court. The Judge found in favor of Cameron and charged Wentworth amounts of $25 "and costs" and $200. In his effort to clean up the city's morals, he hired spies to determine who was frequenting Chicago's brothels. In 1857, Wentworth led a raid on "the Sands," Chicago's red-light district, which resulted in the burning of the area. Wentworth served on the Chicago Board of Education. In 1864, Wentworth ran again for Congress, as a Republican, and was elected for his last term, serving March 4, 1865March 3, 1867. While he was in the House, there was a controversial vote to settle a boundary issue between Wisconsin and Illinois, with Wisconsin claiming land as far as the tip of Lake Michigan. Wentworth was promised that if he voted to give the land including Chicago to Wisconsin, he would be appointed to the US Senate. Wentworth declined the offer. According to city historians in Sandwich, Illinois, Wentworth was one of the key individuals who was responsible for the city getting a railroad stop. The town, which at the time, was called "Newark Station", was given the station, and in turn, the town gave Wentworth the honor of naming the town, which he subsequently named after his hometown, Sandwich, New Hampshire. It is also to note that the boundary line dispute with Wisconsin would have cut through present-day Sandwich, as it straddles the northern border with neighboring LaSalle County, which would have been the State Line had Wentworth not been successful in moving the line north. After retiring from Congress, from 1868 Wentworth lived at his country estate at 5441 South Harlem Avenue in Chicago. He owned about of land in what is today part of the Chicago neighborhood of Garfield Ridge and suburban Summit. When an author left a manuscript of a history of Chicago with Wentworth for his suggestions, he reportedly removed what did not refer to him and returned