Eastwood Insurance

Eastwood Insurance Services is a Fullerton, CA based, American insurance broker founded in 1989, that specializes in automobile insurance. The company has aired several nationally broadcast television commercials, their most prominent ones featuring a cowboy who laments a customer overpaying for insurance and responds, "Should'a, Could'a, Eastwood'a."

The company was fined $300,000 in 1997 for "employing unlicensed people to transact insurance and for acting as an agent for an unlicensed insurer." In addition in 2005 the company was the product of a class action lawsuit alleging that it refused to pay 156 past and current telephone sales agents for overtime worked. The case was unusual in that the court of Santa Ana, California ruled that the plaintiffs, in addition to their settlement of $1.2 million dollars in back wages, should receive an additional $2.1 million dollars in plaintiffs attorney's fees because, "the plaintiffs' legal bill was driven up by unusually protracted and acrimonious wrangling." The company's annual gross income is estimated to be approximately $30 million US dollars. Despite the nationally broadcast television commercials, the company lists direct mail as their biggest marketing channel. The company has recently been bought out.