He's with Tom

But then, maybe gumption is what’s called for. By this past February, the Brady brand that McDonough had helped build had grown
bigger than the Patriots front office could handle. It demanded a dedicated steward. McDonough decamped for New York, to plant his professional flag in the marketing big leagues. He’s now a VP of marketing at Avenue Capital, a $20 billion hedge fund. Chelsea Clinton works there. McDonough knows her, and her mom and dad. Avenue Capital is a place where the connections McDonough has cultivated will serve him well. He’s networking, raising money, making new kinds of deals. It’s the same hustle he honed working for WEEI and the Patriots, only with a lot more zeros attached. Some of those zeros come from Brady: The quarterback is an investor in the fund.

Along with the gig at Avenue, McDonough still represents Brady and is trying to make good as an independent manager of talent. He’s named his one-man management company CAVU, an aviation acronym for "ceiling and visibility unlimited." His website, which features a backdrop of clouds and a bold line-art logo that would not be out of place in 1930s Germany, bills itself as the "portal through which powerful brands have been marrying powerful brands for years." In his new venture, McDonough is said to have already helped Bündchen on a few projects.

As he looks for more clients, the question that will dog him, fairly or not, is whether he can be something more than Brady’s borrowed Rolodex. As if to answer those doubters, McDonough has been showing up sans Brady at soirees for the moneyed class. He skipped a Brady party on the Fourth of July on Beacon Street to watch fireworks with various movers and shakers in Aspen.

The previous month, he appeared without his famous patron at a Celtics dinner in Los Angeles during the NBA Finals. To get there, McDonough hitched a ride on the private jet of Jim Pallotta, a co-owner of the Celtics and the obscenely wealthy hedge fund manager for Tudor Investment Corporation. Another good guy to know.

At the Celtics dinner, which took place at Todd English’s joint Beso, the fact that McDonough was without Brady had some team insiders clucking. "Everyone was kind of joking about him," one guest says. "Some of the people were saying, ‘Who the fuck is this guy? What kind of weird shit is going on?’ He shows up at all these big parties and walks around like the cat’s meow."

Time and again in sports we find strange life forms affixed to the underbellies of athletes. Most are remoras clingy enough to shame limpets. They are the kind that sucked Mike Tyson dry, and ruined Johnny Unitas. McDonough isn’t like that. But that doesn’t stop people from wondering. "A lot of Tommy’s former teammates are pretty skeptical of Will," says a friend. "We have other friends who have been railroaded into doing something with hustlers…. You always worry about guys that do well and have guys that hang around."

Guys that hang around. Or always happen to be in the right place at the right time. Guys who trade their clout on Madison Avenue. Guys whose friends don’t really know them. It sounds weird, all right. But then again, being the greatest quarterback on the planet, taking trips to Ibiza, and waking up next to Gisele sounds pretty weird, too. Maybe Brady needs McDonough to normalize a world that none of us can truly fathom. Maybe.

We can only guess. What’s clear is that for now McDonough seems willing to endure the downside of the wraithlike presence he’s cultivated. He’s happy if Brady’s happy. And lately Brady has been happy. Last year he turned in arguably the greatest single-season performance ever for a quarterback. If he wins another Super Bowl, he’ll join Terry Bradshaw and boyhood idol Joe Montana as the only quarterbacks with four rings. The swagger will be impetuous. The brand will be unstoppable. McDonough will remain invisible.