Tom Brady’s Retirement
Brady is the most successful NFL player in history and had a brilliant career with the Patriots. He quit the franchise after 20 years amid a low-key fallout with Bill Belichick. Then he joined the Buccaneers where he had an Indian summer and won a seventh Super Bowl ring. But somehow, he managed to retire twice during this period (via NPR).

Then there was more drama because fans doubted that he was finished. Speculation mounted and continued to link him to multiple franchises. There was talk of him joining the Raiders after Derek Carr departed. Some people also believed that he would be a great short-term option for his hometown Niners. It was one of the weirdest long-term dramas of this era.