He's with Tom

How it is that McDonough got his foot in the door takes us back to 1996. At 16, most boys were playing Mortal Kombat. McDonough was hustling. He wanted to work at the sports radio station WEEI, and legend has it he called every day asking for a job. But McDonough’s former boss there, Lou Imbriano, has a different version of events: "His dad knew the CFO of our company."

It was the beginning of a familiar pattern: McDonough leveraging a connection to advance himself, then quickly making a positive impact. "There was no sense of entitlement," says Imbriano, now the head of TrinityOne marketing. "I’d ask him, ‘What are you doing on Saturday?’ and his answer was, ‘What do you need me to do?’"

Imbriano recounts one episode during the Patriots’ 1996 AFC championship game in Foxboro. McDonough was sent to the stadium parking lot, tasked with handing out large "Go Pats!" WEEI cards. But he was competing against the team’s marketing crew, which was handing out pompoms in the same spot. "More of the cards were coming into the stadium than the pompoms," Imbriano says. "The next day I got a call giving me a little crap for it."

During his senior year at Westwood High, where he was class president, McDonough started a staffing company to keep up with Imbriano’s demands for manpower at events. In short order, he had a sizable collection of classmates working for him. In 1997, Imbriano signed on as the Pats marketing director, and McDonough went with him. He also enrolled at BC, and started taking classes at the school of management. He worked for the Patriots two to three days a week, gaining experience in sales, community relations, and a host of other marketing subgenres.

When he graduated in 2002, McDonough was given a full-time job in the Patriots front office. Imbriano soon appointed McDonough a player liaison for his marketing group. Now anyone looking for a Patriot to show up at an event went through him. In his new position, McDonough had ample time to pal around with the team. He was roughly the same age as many of the players. He knew the city and liked to go out. But it was Brady, in particular, with whom he connected. The quarterback saw a kindred spirit in McDonough and began seeking him out for advice, not just about team issues, but about Boston, about life.

Was it at this point that McDonough started wearing suits in the locker room? Or driving a BMW 540i? (A Cadillac Escalade, Lexus SUV, and Range Rover would follow.) By 2004, an increasing amount of McDonough’s time was spent dealing with Brady, whose sisters were still handling much of his schedule. But the quarterback had started dating Moynahan. He was a two-time Super Bowl MVP etching his name into the NFL record books. His expanding celebrity demanded a professional-grade filter. McDonough—a friend, a Pats insider, not a sister—was the ideal guy for the job.

Sure enough, Brady’s "butler" was soon everywhere, behaving very little like a butler. People were confused about his position. Was he an agent? An assistant? A bunco man?

"He was always talking about making deals," says McDonough’s friend Roy MacDowell III, a real estate developer with the firm Boulder Capital. There was McDonough partying with members of the team at Union Bar & Grille. There he was flying with Brady to Lindsay Lohan’s New Year’s bash. There he was shooting bull at Sonsie with new BC football coach Jeff Jagodzinski and Robert Withers, an executive at Marquis Jet, a private airline Brady uses. (Neither Jagodzinski nor Withers responded to interview requests.) The people at Sonsie say McDonough became such a regular at the swish establishment and entertained so many heavy hitters there that the owners decided to name a drink after him. It’s called the Will Thrill. Ingredients: Stoli orange vodka, Citrónge, and orange juice topped with sparkling wine.

If one moment stands out in McDonough’s upward scramble during this period, it occurred during a home game against the Jets on December 4, 2005. Gisele Bündchen was at Foxboro that day, handing out Victoria’s Secret prizes and steaming up the end-zone JumboTrons. McDonough knew her from a past promotional project and had surely noted what she’d told the Inside Track after seeing a photo of Brady: "definitely not too shabby." Here was an opportunity for a very sweet deal.

About a year later, on January 14, 2007, mere weeks after Brady formally dumped a pregnant Moynahan, McDonough was spotted with Bündchen in the bowels of San Diego’s Qualcomm Stadium after the Patriots’ playoff win over the Chargers. Bündchen would later tell GQ that "a friend who knew us both" had fixed her up with Brady. A source close to Brady confirms it was McDonough. "Will would smuggle [Bündchen] in," claims a friend of Brady’s. "Tom was on his way out with Bridget. He can’t see Gisele Bündchen without people noticing." A different friend says Brady had ended things with Moynahan several months earlier. And that Brady hadn’t even been on an actual date with Bündchen when she was spotted outside the locker room in San Diego.

No matter. The paparazzi and gossip queens began foaming. In the press, the star athlete and the supermodel were an instant item. In the blogosphere, McDonough was a "pimp," accused of abetting Brady’s supposed playboy lifestyle by planning dates with a bevy of women and keeping it quiet so Moynahan wouldn’t find out. Another view might be that he was simply doing his job—what better way for an aide-de-camp to demonstrate his value than to gift-wrap the world’s hottest supermodel? It was also a shrewd marketing move: Brady and Bündchen have become one of those megacouples whose conjoined fame is greater than the sum of its parts.

By last year McDonough had cemented his place in Brady’s retinue. He had moved into a Commonwealth Avenue penthouse a few doors down from the quarterback’s pad. He started showing up in photographs wearing designer outfits similar to Brady’s. He seemed to develop a Brady "mode" that was different from the laid-back persona his friends remember. People who have dealt with McDonough in a professional setting say he can sometimes be confident to the point of being cocky. On the field, that’s called swagger. Off the field, it’s attitude.

A magazine staffer who worked on a Brady photo shoot last year says McDonough stalked onto the set wearing a navy pinstripe suit and a BlackBerry on his belt and proceeded to behave like a discount David Falk. "He seemed like a cheesy L.A. agent," the staffer says. "Any time Brady would come out in a different look, [McDonough] would be like, ‘Yeah, man, totally,’ or, ‘No, don’t wear that.’ It was never even clear what his role was or if we could tell him to butt out. He just seemed to have opinions on everything. It was escalating into diva-ish behavior."

Brady said little during the photo shoot; McDonough did most of the talking. "[He] was a little bit drunk with his power," the staffer says. "He really seemed like a kid in a suit with a lot of gumption."