A luxury car donated for a raffle by NFL legend Tom Brady back in 2004 has mysteriously vanished, leaving a trail of unanswered questions and intrigue. In 2004, Tom Brady, then the star quarterback of the New England Patriots, won his second Super Bowl MVP award after leading his team to victory over the Carolina Panthers in Houston.
At that time, Brady was already a celebrated champion, having won his first Super Bowl MVP honor two years earlier in 2002. Back in those days, the Super Bowl MVP received a luxurious Cadillac XLR Roadster as part of the award.
With two Super Bowl MVP awards under his belt, Brady found himself the proud owner of two Cadillac XLRs. Not wanting to keep both, Brady decided to put the second car to good use by donating it for a raffle, with the proceeds going to benefit his former high school, Junipero Serra, located in San Mateo, California. It seemed like the perfect solution—a generous gesture that would help raise funds for the school that played a role in shaping his early years.
The raffle was organized with tickets being sold for $25 each, and the luxurious Cadillac, worth around $76,000 at the time, drew a lot of attention. The fundraising event turned out to be an overwhelming success, with Junipero Serra High School reportedly raising $367,000. Principal Lars Lund called it the school’s “most successful fundraiser ever.”
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However, what happened to the Cadillac itself has remained a mystery ever since. The winner of the raffle was announced as Charlie Affrunti, a man whose two sons had graduated from Junipero Serra and even played high school baseball alongside Brady in the 1990s.
Despite being publicly named as the raffle winner, Affrunti has never accepted an interview request in the 20 years since, and the Cadillac has not been seen publicly since the raffle.
According to speculation reported by the Mail, it is believed that Affrunti may not have been able to keep the car due to the associated financial burden. Under IRS regulations, raffle winners are required to pay taxes on their winnings—typically around 25% of the market value of the prize, minus the cost of their raffle ticket.
With the Cadillac valued at $76,000 at the time, Affrunti would have faced a tax bill of approximately $19,000 in order to claim the car. It is possible that the high cost of claiming the Cadillac was simply too much, leading Affrunti to part ways with the luxury vehicle.
Despite the mystery surrounding the fate of the Cadillac, the fundraiser itself was a resounding success for Junipero Serra High School, providing much-needed funds for the institution. As for Brady, the raffle marked just one of the many instances in which he used his growing platform to give back to his community.
Tom Brady’s NFL career continued to flourish after 2004. He went on to win three more Super Bowl MVP awards, adding to his already legendary resume. However, Brady only received one more Cadillac, as the tradition of awarding a car to the Super Bowl MVP was discontinued in 2015. His third and final Cadillac came in 2014, after his victory against the Seattle Seahawks.
Following that, he won additional Super Bowl MVP awards in 2017 and 2020, but no car accompanied those accolades. Brady ultimately retired after the 2022 season, cementing his status as one of the greatest quarterbacks of all time.
While the mystery of the missing Cadillac may never be fully solved, the story is a reminder of Brady’s early years as a champion, his efforts to give back to his community, and the unexpected twists that can come from even the most well-intentioned gestures.
Whether the car was sold, stored away, or simply disappeared from public view, it remains an intriguing footnote in the storied career of an NFL legend.
