The Truth About the Absurdly Charmed Life of Tom Brady

But he did work his butt off, eventually ditching his two-donut-a-day habit in favor of healthier choices, and was actually a three-sport athlete who was drafted by Major League Baseball’s Montreal Expos out of high school in 1995. Knowing he wanted to play football, though, he headed to the University of Michigan, where things went…alright. He was the backup QB for two years before becoming the Wolverines’ full-time starter, going 20-5, including Bowl wins, in the two seasons he started.

“I think being naïve allowed me to accomplish a lot of things,” he told Shepard. “Like when people said, ‘Oh you’re going to go to college and play football?’ I was, ‘F–k, of course I am, what do you think?'” They had a laugh over his premature assumption that all would turn out exactly as he planned. “I look back and I’m, like, the odds to overcome all those things [were incredible].”

After graduation, Brady entered the 2000 NFL Draft as a lightly heralded prospect, and waited. Then waited some more, wondering if he was going to need his resume boasting two summers as an intern at Merrill Lynch after all.