bootlegger A smuggler; a dealer in illicit goods; originally, a dealer in contraband whiskey, so-called because the bottles were often carried hidden in the legs of his tall boots. Though the term gained currency during the era of Prohibition (1920-33), it dates at least from the mid-19th century. It was much used in the dry states of Kansas and Oklahoma in the 1880s. Back formation yielded bootleg, both verb and adjective.

cutpurse A pickpocket, a thief. This term, in use since the 14th century, originally described those who stole by cutting purses off the belt or girdle from which they were hung. Since purses or money-holders are now carried in pockets rather than worn at the waist, the term pickpocket has all but replaced its older counterpart cutpurse.

Dick Turpin Any especially daring or flagrant highway robber or bandit. Dick Turpin (1706-39) was an infamous English highwayman renowned for his criminal derring-do. He appears as a character in William Harrison Ainsworth’s romance Rook wood (1834), as well as in various thriller novels.

five-finger A thief, pickpocket. In this expression, the obvious reference is to the hand and its role in stealing something or in picking someone’s pocket. A similar expression, five-finger discount is used to describe shoplifting, the implication being that by virtue of one’s five fingers, a 100% discount has been obtained. Other similar expressions dealing with the hand’s role in theft are light-fingered, sticky-fingered, and itchy palm.

fly-by-night A temporary and usually unethical business; a poor credit risk; a person or enterprise of dubious reputation or questionable merit. This expression originally referred to a person who defrauded his creditors by hurriedly and furtively leaving town in the dead of night, thus flying (or fleeing) by night. In its usual context, however, fly-by-night is used adjectivally to describe a business which accepts orders and money but folds before delivering any goods or services, leaving both creditors and customers in the lurch. The expression is sometimes used in a more general sense to describe anyone or anything of uncertain character.

footpad A thief or other criminal who operates on foot. This expression refers to the padded shoes worn by a criminal to muffle his footsteps as he stealthily approaches a victim.

hanky-panky See MISCHIEF.

hatchet man A hired assassin; any writer or speaker, especially a journalist, who manipulates words in order to ruin someone’s reputation. The former meaning dates from the mid-1800s when professional murderers actually carried hatchets.

The current figurative meaning, in use since the mid-1900s, refers to character assassination rather than actual murder. Related phrases include hatchet job and hatchet work.

horn-thumb A cutpurse; a pickpocket or purse-snatcher. This obsolete term derives from a thief’s practice of wearing a thimble of horn on thumb for protection against the edge of his knife. The term appears in the 17th-century play Bartholomew Fair:

jailbird A convict or prisoner; an ex-convict or ex-prisoner. This expression, derived from the iron cages to which inmates were formerly confined, usually refers to a prisoner who has spent the better part of his life behind bars.

jaywalker A person who crosses a street without heeding the traffic laws; a presumptuous pedestrian. This expression, derived from the belligerent and defiant jaybird, is commonplace throughout the United States and Great Britain.

lully prigger A thief of the lowest, most despicable sort. The origin of this expression is unknown; however, lully prigger originally referred to a thief who stole wet clothing from a clothesline, and prigger alone meant ‘horse thief’ as early as the 16th century. Today this chiefly British phrase describes any thief.

plug-ugly A hoodlum, thug, miscreant, or larrikin; a gangster; a boisterous, uncouth, physically unattractive person. This term was first used as the self-assumed name of a 19th-century gang that terrorized the city of Baltimore:

Although the gang is long since gone, the expression lives on in figurative contexts:

scofflaw A person who disregards the law. This term is clearly a combination of scoff ‘mock, jeer’ and law. The expression, used during Prohibition for a patron of a speakeasy, now usually refers to someone who ignores traffic regulations or refuses to pay traffic fines.

skulduggery Deceitful or dishonest conduct; underhanded scheming. Derived from the Scottish skulduddery ‘illicit sexual intercourse; obscenity,’ skulduggery is, by extension, often used to describe fraudulent or surreptitious business practices.

tenderloin See LOCALITY.

wetback An unauthorized immigrant. Although in its widest sense this term may refer to any person who illegally enters the country, wetback is most often applied disparagingly to Mexican laborers who wade or swim across the Rio Grande to the United States in search of temporary employment.

Wetback is also frequently used as an offensive epithet for any Mexican-American. In addition, “wet” is sometimes prefixed to the names of various animals which are illegally imported from Mexico by American ranchers.