The AI content licensing landscape transformed dramatically in September-October 2025, shifting from bilateral agreements to systematic marketplace infrastructure. This comprehensive analysis examines the major deals shaping AI search results, including OpenAI's $250+ million News Corp partnership, Reddit's $60-70 million annual agreements with Google and OpenAI, and the groundbreaking Real Simple Licensing (RSL) protocol. The $1.5 billion Anthropic copyright settlement—the largest in history—established a $3,000-per-work baseline that fundamentally changed licensing economics. With 60% of major publishers now blocking AI crawlers and Cloudflare's Pay Per Crawl marketplace launching, the industry faces a critical inflection point. This deep dive reveals how licensing deals directly impact which content appears in AI search results reaching 800 million weekly users, the 93% zero-click problem threatening publisher revenues, and strategic implications for content creators navigating this rapidly evolving landscape.