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Aged 10, appointed captain of his "side" at a spelling bee, he chose the best-looking girls, who proved to be less intelligent than the ugly children, and so lost.
He liked girls, but as friendly and intellectual companions. Said his sister: "He used to correct their grammar when they conversed, and gravely lecture them upon the folly of wearing stays. . . . No village belle ever liked to own that she laced tightly, or that she wore a 'board,' as it was a tacit admission that her figure could not bear unaided the test of the Empire dress; consequently, brother's remarks would be received by his young friends with an injure! air, and a vehement protest against such a false accusation. Brother would then test their truth by dropping his handkerchief and requesting them to pick it up; if they wore a 'board' stooping would be impossible, or, at all events, very difficult. The ordeal would cover them with confusion, when the philosopher of 13 years would resume his moral lectures upon the laws of hygiene and the follies of fashion."
He was ousted from the New York Evening Post's composing (i.e. typesetting) room because that newspaper desired "only decent-looking men about." Said his sister: "He seemed to me the embodiment of romance and poesy, and now, as I think of him, with his pure unselfish nature, so early devoted to what was noblest and best, I can only compare him to the high-minded boy saint, the chaste seraphic Aloysius."
James Gordon Bennett invited him to join him in establishing the New York Herald. Greeley declined. Instead, in 1834, aged 23, he began to publish and edit the New Yorker, a weekly literary journal (in no wise connected with the current smart-chart by that name).
Item from what corresponded to the Miscellany page of the New Yorker:
"A man by name of Tibbetts, a short time since, jumped into eternity and the Kennebec River at one and the same time! Cause, intemperance."
In 1841, aged 30, he founded a New Morning Journal of Politics, Literature and General Intelligence—the New York Tribune (now the New York Herald Tribune). "The immoral and degrading Police Reports, Advertisements and other matter which have been allowed to disgrace the columns of our leading Penny Papers, will be carefully excluded from this, and no exertion spared to render it worthy of the virtuous and refined, and a welcome visitant at the family fireside." Horace was editor; one Thomas McElrath, his partner, was business manager. Among those who worked on Greeley's Tribune at one time or another: Charles A. Dana (famed for the Sun), Whitelaw Reid (father of Ogden Reid, present Herald Tribune owner), John Hay (Lincoln's secretary and Ambassador to England), William Winter (famed critic).
"If I could save the Union without freeing any slave, I would do it—if I could save it by freeing all the slaves, I would do it—and if I could do it by freeing some and leaving others alone, I would also do that." Lincoln penned those lines in a letter to Greeley.
Vexed while traveling by certain citizens of Erie, Pa., Greeley broke forth in the Tribune; "Let Erie be avoided by all travelers until grass shall grow in her streets and until her piemen in despair shall move to some other city. . . ."