After four weeks they landed in Halifax, Nova Scotia, where Bennett briefly worked as a schoolmaster till he had enough money to sail south to Portland, Maine, where he again taught school in the village of Addison, moving on to Boston, Massachusetts by New Year's Day, 1820.

In 1839, Bennett was granted the first ever exclusive interview to a sitting President of the United States, the eighth occupant, Martin Van Buren (lived 1782–1862, served 1837–1841).

[3] The Herald was officially independent in its politics but endorsed for president William Henry Harrison (1840), James K. Polk (1844), Zachary Taylor (1848), Franklin Pierce (1852), and John C. Frémont (1856).

The author Garry Boulard speculates that Bennett ultimately turned against Pierce for not appointing him to a much-coveted post as American minister plenipotentiary (later called ambassador) to France.

Under Bennett's leadership, the New York Herald adopted a proslavery position, as he argued that the Compromise of 1850 would lead to "but little anxiety entertained in relation to the question of slavery, the public mind will be so fatigued that it will be disinclined to think of the matter any further.

Senator and loyal wartime Governor of Tennessee, and his following moderate Reconstruction Era policies and proposals towards the defeated South, following what was thought would have been Lincoln's gentle hand had he lived.

[7] Bennett and the Herald used racist language, advocated for Southern secession, attacked Lincoln for trying to keep the Union together and generally opposed the American Civil War.

In June 1863 the Herald supported a mass anti-war rally in New York City where the war was denounced as an unconstitutional crusade that would lead to freed Blacks flooding North and competing for white jobs.

[13] Bennett's account of the infamous 1836 Helen Jewett murder in the Herald was selected by The Library of America for inclusion in the 2008 anthology titled True Crime.