Tom Brady for FTX

Tom Brady’s endorsement of FTX stands as the most legally consequential deal on this list. The NFL legend took an equity stake in the crypto exchange and starred in ads urging fans to “invest,” only for FTX to collapse in 2022 with $8 billion in missing customer funds. Leading class-action lawsuits named Brady as a promoter, forcing him to pay $45 million in settlements, a cost that makes #8 Oprah Winfrey’s Surface gaffe seem trivial by comparison. The data point—$45 million in legal fees—solidifies this as a cautionary tale of misplaced trust in unregulated markets.