Tom Brady's post-playing career extravaganza has entered a new, more depraved phase. The exceptional fame and resources he amassed during his playing days have not led him to rethink how aging athletes can influence the world. Instead, they have raised the stakes of his tireless pursuit of even more fame and wealth. From gambling and prediction markets to foreign investment funds to crypto, Brady is willing to go to any length to make money. He partners with DraftKings on an NFT marketplace, was sued for promoting FTX, and hawks GLP-1s. He also abuses his lucrative job as a broadcaster to further his cause as part-owner and lead executive of the Las Vegas Raiders. As we prepare for the build-up to a Saudi WrestleMania next spring and potentially Brady vs. Paul in the ring, we are in a new, more depraved phase of Brady's post-playing career extravaganza. This raises a deeper question: what will it take to satisfy Brady's insatiable thirst for attention and wealth? In my opinion, the answer lies in the fact that Brady's contemporaries, such as LeBron James, Kevin Durant, Peyton Manning, and Alex Rodriguez, are also pursuing similar paths. However, Brady's approach is more shameless and relentless. Personally, I think that Brady's behavior is a reflection of the changing landscape of sports and the increasing commercialization of athlete-superstars. The question of what will become of this first wave of generationally wealthy, name-brand athlete-superstars is indeed fascinating, and Brady's actions provide a fascinating insight into this topic.