Someone accused of "wheeling and dealing" is thought to be involved in complicated, if not dishonest, deals in business or politics. The expression is of American origin and means roughly "to maneuver and negotiate energetically in pursuit of one’s interests," often with a negative connotation of shrewdness or unscrupulousness.

One story that has enjoyed some popularity attributes the phrase to gambling in the Old West. According to this story, a "wheeler-dealer" was a gambler who bet heavily on the roulette wheel, hence the "wheeler," and on cards, hence the "dealer." The verb form "wheel and deal" is supposedly derived from the noun. Among the problems with this explanation is a lack of evidence showing "wheeler-dealer" and "wheel and deal" used in the world of gamblers. Evidence of the verb also goes back somewhat further than evidence of the noun, though neither seems to have become common until the 1950s.

A more likely explanation relates to the sense of "wheel" meaning "a person of importance especially within an organization" - the type of person often referred to as "a big wheel." This sense of "wheel" derives from the idea of the person as an essential moving and driving force of the larger machine or organization. The term is often used specifically in connection with leaders of political organizations. A "wheel" is usually adept at achieving his or her goals, and capable of using whatever means are necessary to achieve them.

According to this explanation, the verb form "wheel and deal" came to be applied to the manner and methods of the "wheel," and from the verb arose the noun "wheeler-dealer" to describe someone who wields power in government or business.

A car dealer claiming to be "wheeling and dealing" really means he or she is willing to bargain heavily to make a deal, and is making a play on words based, of course, on the connection between wheels and cars.