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How a car Tom Brady donated to his high school mysteriously vanished after their $367,000 raffle

In 2004, Tom Brady donated a car he had won to his high school, with a local man winning a raffle to take possession of the vehicle. The car has seen mysteriously vanished with no one knowing its status. 

After Brady won his second Super Bowl MVP award in early 2004, he secured a second Cadillac car that came with winning those honors in football’s biggest game. He got the same honor in 2002. 

Since Brady had no reason to have two Cadillacs, aa mid-20s Brady eventually decided to raffle it off for his high school, Junipero Serra in San Mateo, California. 

The Cadillac XLR Roadster was won by a local man named Charlie Affrunti, who had two sons attend Serra, per SF Gate. 

Bernie and Brian Affrunti both played on the Padres’ baseball team with Brady, who graduated on both sides of the now-Fox broadcasters’ 1995 commencement. What happened to the car after the end of the raffle is unknown. 



NFL greats such as Lynn Swann and Emmitt Smith surround the Cadillac with Brady

What happened to the now-NFL broadcaster’s ex-car is unknown after the raffle took place

The mystery continues to this day, even with NFL greats Larry Csonka, Phil Simms, Lynn Swann and Emmitt Smith all posing with the car. Swann himself is a Serra alumnus.

Charlie Affrunti did not respond to multiple interview requests for the story, with the raffle’s winner being the best chance to debunk the mystery. 

One theory has prevailed that is that Affrunti could not afford to keep the car, as it came with a massive tax bill. 

According to the Internal Revenue Service, raffle winners must pay 25 percent of the market value of the prize, minus the amount of the wager for the car. 



With raffle tickets being sold at $25, Affrunti’s bill would have been around $19,000, as the car was worth $76,000 in 2004. 

Brady’s raffle made the school a reported $367,000, or nearly five times the value of the Cadillac luxury car. 

Even the best running car starts to sputter out after years of wear and tear, meaning the vehicle is likely out of commission and never to be found again.