Let’s try this again. It’s over.

On Wednesday, a year to the day after his last attempt, Tom Brady announced his retirement from professional football. “I know the process was a pretty big deal last time, so when I woke up this morning I figured I’d just press record and let you guys know first,” he said in a 53-second social media video. “It won’t be long winded; I think you only get one super emotional retirement essay and I used mine up last year.” Representatives from Brady’s camp did not reply to a request for comment.

Brady, 45, exits the sport as a surefire Hall of Famer and arguably the best to play his position, with NFL career records for passing yards (89,214), passing touchdowns (649) and Super Bowl victories (seven). The sixth-round pick turned three-time MVP similarly dominated financially as well, earning more than any player in league history. Forbes estimates that Brady got paid more than $530 million over his 23 NFL seasons: $333 million from playing contracts, according to Spotrac, and roughly $200 million from his endeavors off the field. For the first time since Forbes began ranking the NFL’s highest-paid players in 2010, Brady claimed the top spot this season, with expected total earnings of $75 million.

That kind of dominance is a recent development for Brady, who for years passed on most endorsement offers. As recently as 2019, he was earning $12 million annually off the field, a figure that has nearly quadrupled since thanks to lucrative partnerships with brands like Fanatics, Hertz, Subway and Under Armour. Brady, who still had one of the 10 best-selling jerseys in 2022, according to Fanatics, has also escalated his entrepreneurial efforts. He has been the driving force behind five companies as founder or cofounder: nutrition and training brand TB12, a non-fungible token enterprise called Autograph, film and TV content company 199 productions, the “Brady” clothing line, and another media outfit he launched with Pro Football Hall of Famer Michael Strahan and sports documentarian Gotham Chopra. In October 2022, Brady also joined an ownership group for a Major League Pickleball expansion franchise that will debut in 2023.

Yet Brady’s return to football this season, after a highly publicized and dramatic retirement saga in 2022, has proven to be tumultuous. On the field, the Tampa Bay Buccaneers barely scratched their way into the NFL playoffs with a record of 8-9, only to suffer a first-round defeat against the Dallas Cowboys. Off the field has been more complicated.

Brady’s non-fungible token company Autograph raised a $170 million funding round last January and announced a partnership with the PGA Tour in September, all while the NFT market has cratered in 2022. Average NFT trading volume, measured in dollars, has fallen 92% from $17.1 billion in January to $1.4 billion in December 2022, according to Dune.com. Then, in October, Brady announced he and his wife of 13 years, supermodel Gisele Bündchen, finalized their divorce, though financial terms of the settlement were not disclosed. It had been the subject of tabloid speculation for months prior.

Meanwhile, the Brady-endorsed crypto-exchange FTX collapsed under the weight of financial malfeasance and filed for Chapter 11 bankruptcy in December. Brady and Bündchen, signed on as ambassadors in 2021 and starred in a now rather infamous commercial. The financial terms were not disclosed. Brady and Bündchen also received equity as part of the deal, with bankruptcy documents showing that he had about 1.1 million shares of the now wiped-out entity while his ex-wife had roughly 690,000 shares. Forbes previously estimated that, before crypto prices fell and FTX collapsed, their stakes were worth $45 million and $25 million, respectively.

Still, Brady has plenty ahead. This week Paramount Pictures’ “80 For Brady,” a feature film that he produced and appears in as himself, will hit theaters. Brady also reportedly agreed to a 10-year deal with Fox Sports this past May to become a broadcast analyst. It was set to kick in as soon as Brady hung up his shoulder pads. Fox did not reply to a request for comment.

A native of San Mateo, California, Brady turned pro in 2000 after the Patriots drafted him 199th overall out of the University of Michigan. He found success the following year, after an injury knocked out incumbent starter Drew Bledsoe and elevated Brady to the lead role. The Patriots won their first Super Bowl that season, defeating the then-St. Louis Rams. Brady added five more rings in New England and one more in Tampa Bay after joining the Buccaneers in 2020. Brady had previously outlined a goal to play until he was 45, extending it even further when he told ESPN in October 2021 that he could “literally play until I’m 50 or 55 if I wanted to.”

Editor’s Note: This version of the story recalculates the percentage change in the NFT market.