Tom Brady

In the Clutch

After leading the University of Michigan to an overtime victory in the Orange Bowl, quarterback Tom Brady's picked in the sixth round of the NFL draft by the New England Patriots. In 2001, he works his way up the roster, earning the primary backup quarterback position.

Dating Bridget Moynahan

Brady finds his starlet match in former model and actress Bridget Moynahan. Though the ultra-private couple rarely discuss their relationship, Moynahan tells The Boston Herald in 2004, "We both have incredible respect for each other, and each other's lives and professions."

December

A Rocky Start

After three years together, Moynahan and Brady call it quits. Soon after, he begins dating supermodel Gisele Bündchen. The couple are vacationing in Paris when Moynahan reveals she is pregnant with Brady's child. "When you're suddenly pregnant and no one is standing by your side … it's a hard conversation," Moynahan says in a rare interview with Harper's Bazaar.

October

The Face of Style

Brady appears on one of 10 commemorative covers celebrating GQ's 50th anniversary, and the all-American QB finds himself in good company among the likes of Paul Newman, Muhammad Ali, President John F. Kennedy and Michael Jordan. "We liked the fact that Tom Brady represents today," creative director Jim Moore says. "He's got a great spirit about him and he's an incredible leader."