Here’s an illustration I did for today’s New York Observer. The article is about newly elected Mayor Bill De Blasio’s potential picks for the city’s many top jobs. The Observer’s Creative Director Lauren Draper wanted to go with a Wheel of Fortune theme for this one. As is typical, I submitted several sketches (seen below) before settling on one that put the emphasis more on the wheel than De Blasio himself. This was originally supposed to run as the cover for the issue, before everyone found out about the untimely death of the Observer’s long-time and much-beloved editor Peter Kaplan, so this got bumped inside the issue. De Blasio was painted entirely in Photoshop, whereas the wheel was mostly constructed in Adobe Illustrator with some PS textures added later. Thanks to Lauren for another fun assignment.