When you let your boss win.

Well yeah. He’s seen all the others naked. Probably more than seen.

I had to give this a think. This is what has to be in Riker’s head, every game. Each player has a critical flaw that must be exploited.

• Worf is going to make a lot of bold moves and will double-down on a bet. Even if it’s bad. Even if he’s obviously bluffing. Doing otherwise is basically surrendering.
• Data will play the odds, every time. He’s getting better at reading blood pressure and facial expressions, but this means you can misdirect him pretty easily.
• Deanna can read your emotional state so just keep thinking about that last shore-leave on Risa. She can also get overwhelmed with a lot of “loud” emotions at the table, so antagonize Worf every so often; works great.
• Geordi might be tempted to abuse his visor, so pay attention to how he reads the table. For some reason, he starts making mistakes whenever holodecks enter the conversation.

It’s simple, If anyone else ever wins you just claim they are cheating, point out the obvious way they could be cheating and everyone agrees, you are the defacto winner except for worf who’s to thick to understand that.