Jack Henderson on tipping

A witty, rambling letter finds its way from Jack Henderson to his friend Billy, using the everyday ritual of tipping as a springboard for sharp social satire. Set in bustling Detroit, New York, and Atlantic City at the turn of the twentieth century, Henderson sketches the unwritten rules that govern how much a traveler should part with, turning simple meals into a study of etiquette, greed, and pretension.

His anecdotes swing from a bewildered waiter at Shanley’s who dares to return change, to gilded cafés where tiny portions demand oversized tips, and even a chance encounter with a hat‑room attendant who pockets a tidy daily sum. With a mix of street‑wise humor and pointed observation, Henderson exposes the double standards of the service world—who gets thanked, who gets ignored, and how money silently maps class and race. The result is a lively, conversational portrait of an era’s “art of tipping,” delivered with the casual charm of a friend sharing a scandalous secret.