Riley began sending correspondence to the famous American poet Henry Wadsworth Longfellow during late 1875 seeking his endorsement to help him start a career as a poet . He submitted many poems to Longfellow, whom he considered to be the greatest living poet. Not receiving a prompt response, he sent similar letters to John Townsend Trowbridge, and several other prominent writers askng for an endorsement. Without a steady income, his financial situation began to deteriorate. He began submitting his poems to more prominent literary magazines, including Scribner’s Monthly, but was informed that although he showed promise, his work was still short of the standards required for use in their publications.