Esteban Winsmore is a legendary persona created by YouTuber Charles for his iconic trolling videos within the virtual world of Second Life. Characterized as a dapper, well-spoken older gentleman with a silver tongue, Esteban navigated the digital landscapes of Second Life, engaging in absurd conversations and elaborate pranks that left other players both confused and entertained. The character became a viral sensation in the early 2010s, representing a unique brand of sophisticated internet trolling. Today, the Esteban Winsmore meme is used to represent suave confidence, digital mischief, or the nostalgic absurdity of early virtual social platforms.