Sherman retired from public life after resigning as Secretary of State. Except for one day, Sherman had spent the previous forty-two years, four months, and twenty-two days in government service. He gave a few interviews in which he disagreed with the administration's policy of annexing Puerto Rico and the Philippines. Later that year, his wife, Margaret, had a stroke; she died two years later on June 5, 1900. Sherman continued to alternate between houses in Mansfield and Washington. He mostly remained out of politics, except for a letter he wrote endorsing George K. Nash for Governor of Ohio in 1899. Sherman died at his Washington home on October 22, 1900, in the company of his daughter, relatives and friends. After a funeral at St. John's Episcopal Church in Washington, he was interred in Mansfield City Cemetery with his wife.