While you may not agree with the grammarian who asserted that "a long and learned word like this should only be used under the stress of great need," you might find that remembering how to spell "eleemosynary" makes you tend to use its synonym "charitable" instead. The good people of early England had mercy on themselves when it came to spelling and shortened the root of "eleemosynary," the Latin eleemosyna, to "ælmes," which they used as their word for "charity." (You may be more familiar with "alms," an "ælmes" derivative that came to denote food or money given to the poor.) The original Latin root was resurrected in the early 17th century to give us the spelling challenge of the adjective we feature today.