Cartoon drawing of a red Cadillac with LED head lights. ASK ME HOW WIN A CADILLAC are in all capital letters, with ASK ME HOW written in purple letters above the car and WIN A CADILLAC written in red letters below the car. There is a Florida Lottery logo to the left side of the button. The entire button is yellow.
This button is most likely from the Florida Lottery’s LOTTOMOBILE car giveaway. LOTTOMOBILE was a program initiated by the Florida Lottery which gave away a number of cars of various makes and models using a mail-order form. For example, in 1996 the Florida Lottery gave away 25 Cadillac Seville's to a number of lucky winners.
Source: Orlando Sentinel. (1996). "No One Takes Top Prize": Lotto Pot At $17 Million.