Chipman spoke at a Republican nominating convention on March 7, 1871, where he said, "If there was anybody here who didn't want his children placed in mixed schools he had better take them out of the District of Columbia." The statement was drawn out of Chipman after persistent questioning from someone in the crowd, and it caused quite a stir, considering that Republicans generally avoided committing on the subject of school integration in order to not alienate moderate white Republicans. Due to his friendship with Grant, name recognition, longer residency in the District, and his connection to the District's government, the convention decided to nominate Chipman over Frederick Douglass to be the Republican nominee for the District of Columbia's first delegate to Congress. While campaigning, Republicans advocated for long-time District resident Chipman over Democratic candidate Richard T. Merrick, who they said owned no property in the District. This argument backfired when it was revealed that Chipman had sold his home and was living at a hotel, while Merrick actually did own real estate in the District. During the April general election, Chipman won, receiving 15,196 votes to Merrick's 11,104. Republicans won fifteen of the twenty-two members of the District's House of Delegates as well.