Monopoly is from New York, but moved to Los Angeles in 2006. He found working in L.A. was easier because of the many billboards in the city, while in L.A. he was mentored by the well-known street artist, Mr Brainwash. Monopoly is best known for his tuxedoed and top-hatted graffiti character of the Monopoly Man, an idea originally inspired by the stockbroker Bernie Madoff. According to John Wellington Ennis writing for the Huffington Post, "In an era of billion dollar bailouts for banks that already own the country and moguls decrying regulation as un-American, the re-contextualization of the childhood symbol of success and wealth almost needed no explanation." Monopoly also pastes up images of Jack Nicholson. Although graffiti continues to be conveyed as a crime, in his feature in Juxtapoz Magazine, the artist discussed his best efforts to avoid the vandalism aspect of the street art world: "I stay away from mailboxes, highways, freeways, and basically any federal and government property. I like warehouses and abandoned buildings. For example I would never hit a coffee shop like the one we’re in: they [the owners] are trying to make it just like I am. I try to be as positive as I can about what I put out there and I try to do it with imagery everyone can identify with. Most people walking by my stuff are not graffiti people or art people, so figuring out a way that everyone can identify with my work is important." In November 2010 he had his first solo gallery show in New York. In December 2010 he took part in an exhibition at the Mondrian Hotel as part of Art Basel Miami Beach. In 2013 he hosted a yacht party at Art Basel Miami Beach, sponsored by Samsung. At his Los Angeles solo show in 2013 one of his pieces sold for $3 million. He has been pictured hanging out with celebrities and buying expensive cars, leading to accusations by his critics of selling-out. In December 2013 Monopoly created a piece of work, painted 'live' on a piece of red carpet, to publicize Justin Bieber's concert documentary, Justin Bieber's Believe.