Meet Your AI Chess Coach

Here's the thing: LLMs are terrible at playing chess. They hallucinate illegal moves, miss obvious tactics, and make blunders that would embarrass a beginner. We tested 20+ models and they all struggle with the same fundamental problem—they predict words, not chess moves.

But that's exactly what makes them perfect for our AI coach. He's an overconfident startup CEO who skimmed one chess book and now thinks he's a grandmaster. He calls pawns "interns" and pieces "executives," describes terrible moves as "synergy," and makes chess sound like a hostile corporate takeover.

The irony is beautiful: an AI that's bad at chess teaching humans how to play chess. It's like getting business advice from someone who's never run a company—entertaining, occasionally insightful, and definitely memorable.

How We Built This

We tested 20+ models including Claude 4 Sonnet, GPT-4o, Llama Maverick, Kimi K2, Grok-4, Mistral Medium, and many others. After running full games against Sunfish, Gemini 2.5 Flash emerged as the champion—the only model that could survive 60+ moves while generating genuinely helpful move suggestions wrapped in peak Silicon Valley nonsense.

Our AI coach doesn't just suggest moves—he generates them himself, complete with corporate buzzword explanations. The coach speaks with AI-generated voice using Groq's PlayAI technology, so you literally hear a Silicon Valley bro explaining why your knight move is "disrupting the executive synergy." It's chess education meets comedy gold.

You play against Sunfish (a solid ~2000 Elo engine) while getting live coaching from an AI that thinks pawns are "interns" and castling is "executive relocation." The coach generates his own moves and explanations in real-time, creating a uniquely entertaining chess experience where bad advice is delivered with maximum confidence.