Randy Moss was already nine seasons into his NFL career when he snuck up to Tom Brady’s hotel room. Brady didn’t understand why Moss wanted to talk to him. The two weren’t teammates, and the conversation seemed to come out of nowhere. Only later did Brady realize Moss had a much bigger objective: finding a path away from the Oakland Raiders and toward a fresh start.

“So Randy, when he was at the Raiders,” said Brady on the New Heights podcast. “We were playing in ‘ 06. We were playing at Minnesota. It was a Monday night game. He flew after a game to meet at a team hotel. And of course at the time, I’m like, I don’t know. I’m not like I’m the general manager or anything. He showed up, and they’re like, ‘Tommy, Randy’s here.’ So I went and saw him. He’s like, ‘Yo man, I love the way you play, man. I want to figure out how to make it happen.’ I’m like, all right. Why are you talking to me?”

The incident dates back to October 2006. The New England Patriots arrived in Minnesota for a Monday Night Football game against the Vikings. Moss reportedly used a connection via his former teammate, Patriots wide receiver Doug Gabriel, to locate the Patriots’ team hotel. Following that, Moss put a hood on, bypassed security, walked straight through the lobby, and climbed the exit stairs to avoid detection by hotel staff and coaches to meet Tom Brady.

The Raiders were coming off a 4-12 season in 2005, and yet again, the 2006 season was turning out to be similar for them. To back that up, Moss even registered one of his career-low 553 receiving yards that season. So, like any ambitious player would wish, the wide receiver desired a change. Hence, he approached Brady, who stood as a three-time Super Bowl-winning quarterback at that.

Since Brady didn’t have the authority to decide player signings, he was puzzled by the way Moss approached him. But during the 2007 NFL Draft day, the Raiders eventually traded the wide receiver away to the Patriots in exchange for a fourth-round pick. However, Moss’ existing contract structure could not fit under New England’s rigid salary cap, and Moss was hesitant to lose money.

So, to clear the logistical hurdle, Tom Brady restructured his own contract and converted a substantial portion of his base salary into a signing bonus. This cleared the exact cap space New England needed to accommodate a revised deal for Randy Moss.

The wide receiver made his debut in the Week 1 clash against the New York Jets. He then went on to play four seasons for the Patriots and Brady till 2010. In 52 games for the franchise, Moss racked up 3,904 receiving yards and 50 touchdowns while sharing a great camaraderie with his franchise quarterback.