Early in his career, Gwynne was part of the group of journalists and writers including also Rudyard Kipling, Perceval Landon, Julian Ralph and F.W. Buxton who helped start a newspaper, The Friend, for Lord Roberts for the British troops in Bloemfontein, the newly captured capital of the Orange Free State during the Boer War. Later, "[l]ike many another elderly Conservative in the nineteen-twenties [Kipling]'s reacted at the news of events in Ireland, Egypt, India, by moving further to the right in politics." Gwynne's Post "continued to fight its rearguard action, and [Kipling] continued to urge Gwynne to take stronger stands." Kipling "was for years closely associated with the editorial policy of the Post and on terms of friendship with Lady Bathurst ..., [and] spent many week-ends at Cirencester." Gwynne's relationship with Kipling continued close throughout the latter's life—he was a pallbearer at Kipling's 1936 burial in Poet's Corner at Westminster Abbey.