Etymology

bold move, Cotton

Today it means: Expresses skepticism over the potential for positive outcomes of someone else's bold actions. Full definition →

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The story

A modification of a quote, "It's a bold strategy, Cotton. Let's see if it pays off for him." from the 2004 film Dodgeball: A True Underdog Story. Cotton is the name of the character in that film addressed by that quote.

Etymology from Wiktionary, CC BY-SA 4.0.