Do you have trouble spelling? If so, you’ve got a friend in Daniel Webster, the father of the first popular American dictionary. Lately I’ve been reading bits of H.L. Mencken’s book from 1921, The American Language, and enjoyed the section on American spelling and Webster.

Already a superstar in lexicographical circles, Webster’s first dictionary in 1806 made him a household name. The most popular dictionary in the U.S. prior to his was published by an Englishman, Samuel Johnson, who made no secret of his disdain toward the new republic’s scrappy citizenry and its rowdy ways with the alphabet.

Americans took a near-patriotic stance in embracing the new book and its reforms, which were rooted in a quote by Benjamin Franklin that “those people spell best who do not know how to spell.” As such, Webster dropped silent letters and advocated phonetic spellings. Many characteristically direct American spellings exist thanks to him, including jail and wagon, instead of gaol and waggon.

Taking the opposite tack of Johnson’s directives, Webster removed the u from -our words such as colour and honour, flipflopped the ending of -re words including centre and theatre, and changed the c in words like defence to an s. Of course, Americans still adhere to these conventions of Webster’s today, while Brits have stuck with the “original” spellings.

But many of his proposals viewed now resemble an F-worthy fourth-grader’s spelling test. Webster listed tongue as tung, group as groop and women as wimmen, not to mention the appropriately heinous hainous. Across the board, he deflowered ph- words (such as phantom) to start with an f. He mercilessly muted silent letters: thumb was stubbed to thum, island became an iland and leopard lost a spot as leperd.

Many of these edits do make at least some practical sense, falling in line with those anti-British revisions that took root. However, later in life, Webster was dogged by his opponents for the arbitrariness of his reforms. One typical argument would ask, for instance, why he would change the c to an s in words like offense, but spell fence that way.

Time has been kinder to Webster, revealing that his spelling simplifications were a giant step forward for a country that had a very, shall we say, flexible orthography in its youth, one that allowed people to spell eternal as aetaernall, for example, and get away with it. On the other hand, bad spellers still aren’t helped much by a language that, despite Webster’s efforts, has more exceptions to its spelling than rules.