CREATIVE PROMPT

Well based on the simple idea of elimination, we can quickly and safely rule out positions such as "under the table", "trap in their dressing room", or "at their house in the middle of the night". Too many witnesses and security. So we need an opportunity that seems like a normal, every day thing.
Target: Player's favorite restaurant in their city. If they are already home, and going to a place that is familiar, then their guard should be down.
When: We need a comprehensive schedule and we need to look for the pattern. We need to know what the night time routine is for the restaurant. How they clean, what do they look for. If they don't look under the tables, then a simple remote controlled smoke bomb attached to the underside of the table. If that seems unlikely to work, then underneath the garbage bag in the bathroom is an option, or if the vent is easily accessible, then lock the door and get that vent cover off, then it's just a mater of putting it inside. Now, the visit to the restaurant can look pretty non suspicious, just go 2 days before you think he may be going. If he always goes before game night, or always goes on an off night those are good targets.
How: Simply post a sentry outside the restaurant, and if he visits it's game on. Activate the smoke bomb 55 minutes after entry, and simply wait for the chaos of the evacuation. During evacuation, blend in with the crowd, get up close behind and fire.

Boom, done and no one knows.