Posted by James Briggs on August 02, 2001
In Reply to: Wheeler-Dealer posted by Bruce Kahl on August 02, 2001
: : Connoting scam or substandard salesmanship?
: Maybe both.
: wheel and deal
: Operate or manipulate for one's own interest, especially in an aggressive or unscrupulous way. For example, Bernie's wheeling and dealing has made him rich but not very popular. This term comes from gambling in the American West, where a wheeler-dealer was a heavy bettor on the roulette wheel and at cards. [Colloquial; c. 1940]
: The American Heritage® Dictionary of Idioms by Christine Ammer © 1997 by The Christine Ammer 1992 Trust
If someone is said to be wheeling and dealing then they involved in setting up important arrangements, often involving money. Big wheel is a phrase use to describe an important person and this may be the basis of the saying. Much more likely however is a custom of the old Billingsgate fish market in London. The fish was wheeled in, prior to the dealing which could only start at a certain pre-determined time.
An alternative explanation comes from the US west where a big Wheeler and Dealer was a heavy better at cards and roulette wheels. I prefer the fish market version.