In 1990’s, the circumstances of being a contestant on a popular game show were published in a trendy question and answer column in Parade Magazine. If contestant switched from the initial choice to a second choice offer by the host, would the chances of winning the desired prize be increase? The columnist’s response to the reader sparked a good deal of controversy among mathematicians. Shortly after the publication of this answer, articles appeared in various mathematical publications some supporting and some refuting the columnist’s answer. This document reports the results of research into the controversy generated by some of the probability problems used on Let’s Make a Deal game show. Using a variety of approaches and assumption, the author attempts to formulate mathematical proof to explain the correct answer to the contestant’s question, “Should I switch?” / text