The 'Now Why Is That?' meme originated from an episode of ESPN's First Take in July 2022, featuring NBA reporter Brian Windhorst. During a segment discussing the Utah Jazz's trade of Royce O'Neale, Windhorst delivered a masterclass in suspenseful storytelling, using his index fingers to point upward and repeatedly asking, 'Now why is that?' to hint at a larger organizational shift—which later turned out to be the blockbuster Rudy Gobert trade. The clip went viral for Windhorst's dramatic delivery, theatrical gestures, and the 'insider' energy he projected. Internet users quickly adopted the template to highlight suspicious behavior, corporate maneuvers, or any situation where a series of events suggests a hidden, deeper motive.