He's with Tom

Tom Brady appeared to the world in his underwear on April 16, 2005. The occasion was Saturday Night Live. A skit called for Brady to play a pants-less stud who charms ladies in the workplace. Even in briefs, Brady flashed some élan. For the reserved quarterback, it was a ballsy, half-naked bootleg into the New York limelight.

Already, Brady was dating a beautiful actress. Nestled among her boyfriend's family, Bridget Moynahan beamed from the front row. Also watching were some of Brady's closest friends on the Patriots, Dan Koppen and Larry Izzo. In their way, they had all helped lay the foundation for Brady's burgeoning celebrity. And now, in his way, he was leaving them behind to crack into a new realm of stardom, a world that would soon offer up GQ covers, Visa endorsements, and Brazilian supermodels. Only one person in the audience that night would join Brady on this catapult ride to greater fame. His name was Will McDonough. He was an unexpected choice.

McDonough first pinged on the public radar three days after the SNL show, popping up in that fabulous junkyard of faux journalism, the Boston Herald's Inside Track. He was described therein simply as "Tom's bud." In the years to come, as it grew apparent to hacks and flacks across town that Tom's bud had been entrusted with a mysterious authority over Tom, McDonough became something more. He was Brady's "assistant" or his "Man Friday." When the gossipmongers were in a less generous mood, he was called a "butler" or a "pantry man."

But McDonough's role in Brady's life has always been more substantial. For those who don't remember, Brady was not all that long ago a floppy-haired underdog who favored blazers with elbow patches. Even after his early on-field success, he retained a dorky aw-shucks style. He hated the podium and was unprepared for celebrity. Then, before our eyes, he became the metrosexual who now flits about Europe, paparazzi in his wake. These days Brady seems quite comfortable in his underwear, accessorized perhaps with a sweaty bottle of Smartwater and some Stetson cologne. Compared with Peyton Manning, who hams it up for the NFL's yeasty audience and wouldn't be caught dead in a Movado watch, Brady is a fey extraterrestrial. He has leveraged his appeal in a restrained fashion that transcends his sport. The approach might even be called elegant. But the process has not been intuitive. Brady has needed help. That's where McDonough comes in.

Although his duties are shrouded in secrecy, McDonough is a de facto manager; he brokers deals and acts as a gatekeeper. Brady seems to trust him implicitly. McDonough has had a major hand in the quarterback's metamorphosis—and along the way has become an important man in his own right. One weekend, the Boston College grad might be hobnobbing with hedge fund managers. The next, he could be jetting to a celebrity-studded party. Always, he remains deeply connected to Brady as both a business associate and a best friend. Their relationship raises eyebrows, not least because of its clandestine nature. On the Patriots' payroll until this past February, McDonough has now left the team to handle Brady's affairs on his own. He has no official title. His business card simply lists his name, phone, and e-mail. It's all so East Berlin.

Among both casual observers and Brady's friends, the question comes up time and again: Just what in hell does Will McDonough do?

No one fully knows.