Henry Jarvis Raymond was born in Lima, New York to a farm family that had migrated from Connecticut. Raymond distinguished himself at the University of Vermont where he was graduated with high honors in 1840. During his college career he developed strict work habits and began submitting pieces to Horace Greeley’s New Yorker . He moved to New York City after college and pursued freelance writing until he earned a job with Greeley. Thus began a lifelong enmity between the two men whose views of the role and utility of journalism differed greatly. When Greeley founded the New York Tribune in 1841, his problems with Raymond did not stop him from offering the younger man a job as his chief assistant, a testament to how the older man valued Raymond’s skills and abilities (Darby 353-4; Wilson 373).

Raymond soon formed a close friendship with Pfaff’s visitor George Jones who worked in Greeley’s business office. Though lacking in start-up funds, the two were inspired with the dream of starting a paper of their own. It is speculated that Raymond knew others of the Pfaff’s crowd, such as Fitz-James O’Brien (Wolle 48, 53, 67). He may have belonged, along with Walt Whitman, to the “Fred Gray Association,” a group of young men who “drank and caroused together at Pfaff’s and elsewhere” (E. Miller, “Introduction” 11). The evidence to suppport his connection to this group of male friends, though, is somewhat tenuous because Walt Whitman only recorded the individual as "Raymond" without any further information about his identity (Blalock 50). No other concrete connection to Pfaff's can be established besides his possible membership in the Fred Gray Association.

During this time, Raymond took work at the Morning Courier and the New-York Enquirer . He eventually became managing editor of Harper’s New Monthly Magazine , a position he held until 1856. Raymond followed through on his partnership with George Jones in 1851 with the formation of the New York Daily Times (later renamed the New York Times ). He edited the paper while Jones ran the business office. In contrast to Greeley’s Tribune , Raymond’s paper advocated impartial, measured judgment, a move which may have been responsible for its immediate success. It gained twice the Tribune’s circulation even though Greeley engaged in aggressive competition (Darby 353-4).

In addition, Raymond actively pursued his political interests. Thanks in part to his reputation as a newspaperman, an orator, and a political strategist, he was elected in 1849 to the State Assembly. He aligned himself with the Free Soil contingent led by William Seward and won re-election in 1859. The competition between Raymond and Greeley continued in the political arena when Raymond beat Greeley for the nomination for Lieutenant Governor. Raymond’s accession to that office and his enthusiastic support of Abraham Lincoln at the 1860 Republican Convention contributed to Lincoln’s victory (Darby 354-9).