Super Bowl XLII
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Tom Brady is the winningest quarterback in NFL history. He's the owner of seven Super Bowl wins and five Super Bowl MVPs. Brady was also on the losing side of the second-biggest upset in Super Bowl history, a loss that led to many sleepless nights. 

The loss was New England's 17-14 setback to the New York Giants in Super Bowl XLII. The loss prevented the Patriots from joining the 1972 Dolphins as the NFL's only perfect teams. The weight of that loss was felt immediately by Brady, who played that game with an ankle injury that was sustained during the AFC Championship. 

"We were crushed," Brady said on Apple TV's documentary on the Patriots dynasty. "I was crushed. That was our history-making game. That would have been everything. ... We were as devastated as you could be. There was no sleep. There was no sleep for a long time." 

Brady wasn't the only Patriots player who felt the weight of the loss. Team president Jonathan Kraft offered a graphic visual of the postgame locker room looked like. 

"I'm watching guys throw up and cry on the floor," Kraft said in the doc. "I've never seen that. I've never, ever, seen that." 

For Randy Moss, there's one play from that game that continues to live with him. With 19 seconds left, the Patriots needed a big play in order to get into field goal range. Brady scrapped the play that was called upon entering the huddle. 

"Tom told me, 'Hey Randy, we canning that,'" Moss recalled. '"Run the play. When I look at you, reverse field.'"

When rewatching the play, you can see Brady nod, then point in Moss' direction before launching a deep pass down the far sideline. Moss got past both of the defenders covering him, but the pass was deflected before Moss was able to get two fingers on the ball. The ball ultimately fell to the turf as an incompletion. 

Had Moss caught the ball, the Patriots would have been in field goal range. Instead, New England ran out of hope on the next play after Brady threw another incompletion on an attempt to Moss. 

"That still haunts me," Moss said. "My fingertips touched it. I nipped it." 

While loss prevented them from reaching immortality, the 2007 Patriots continue to live on in history. In 2019, they were tabbed as the seventh-best team in the NFL's first 100 seasons. Each of the teams ahead of them on the list won the Super Bowl. The 1990 Bills, who came in at 35 on the list, are the next-closest team that didn't win a championship. 

The defeat also temporarily prevented the Patriots from validating their previous three Super Bowl wins in light of Spygate, which was brought to light earlier in the '07 season. Brady and the Patriots would eventually get their validation after winning three more Super Bowls in the 2010s.