Sean Avery in the Neutral Zone

The NHL’s black sheep, and Hickey Freeman’s latest pitchman, considers life without hockey.

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Sean Avery

Photo By Lexie Moreland

Appeared In
Special Issue
Men'sWeek issue 02/16/2012

“I think Sean’s really working on that,” says Tom Sachs the artist, who is one of Avery’s oldest New York friends. “That’s a life project: controlling your anger and learning to channel it in a creative way is something that will be a life project for Sean. You can’t remove that from what makes him a great spontaneous, psychological player. There’s a fine line between being purely intellectual and totally impulsive. Yeah, I’ve seen Sean freak out, and I think it’s maybe his strength and his weakness, but they’re integrated.”

It’s also proving difficult to reconcile the kinder, gentler Sean Avery with the one who has a world-class reputation for mind manipulation. By professional hockey standards, Avery’s build is average. The Whale’s roster lists him at 5-feet, 10-inches tall and 195 pounds. He’s made his career as an enforcer not by brute strength, but by tweaking his opponents at near psy-ops levels. His greatest hits list is long, but is perhaps best illustrated by a 2008 playoff game incident in which he ignored the puck to face guard Devils goalie Martin Brodeur. Though not technically illegal at the time, the screening move flouted any notion of sportsmanship. It immediately prompted a rereading of NHL rule book and resulted in what is now called “The Sean Avery Rule.”

Avery is the back of a Town Car on his way to the Meatpacking District offices of Lipman, the advertising and creative services agency discussing his career path. “I didn’t think there was anything else I was going to do; I wasn’t thinking about anything else,” Avery says in his still-there Canadian accent. He grew up outside Toronto, was signed by the Detroit Red Wings at 19 and broke into the pros at 21.

“If I had said, ‘You know what, I’m gonna go to school, I could have went to Harvard,” he goes on. “I could have went to Yale. I could have went to Brown. I could have…anywhere. If you get a hockey scholarship, you can go anywhere. You just gotta get by on those SATs....I always have this image in my head of walking around one of those campuses to class and then going to practice. Just being superpreppy, that all-American picture.”

In major American sports, you’d be hard pressed to find an athlete with as deep an interest in fashion as Avery. In the summer of 2008 he spent a few weeks interning at Vogue. (There is a portrait of Anna Wintour on the wall of his apartment. “For Sean,” the signed inscription reads, “our most famous intern.”) He worked as a “design collaborator” with the men’s wear line Commonwealth Utilities. He had been renting the house in Los Angeles to Milk Studios founder Mazdack Rassi. Throughout his career, Avery has shown an almost innate need for extracurricular stimulation. Tiny’s, a restaurant and bar he co-owns, is about 10 blocks south of his apartment, and Warren 77, the first bar he opened, is a few blocks past that. Last summer, in a significant move for a pro athlete, he filmed an Internet ad in support of the campaign to legalize gay marriage in New York.

Now, Avery is facing life without hockey, and the prospect that the outside interests are all that he may have.

Lipman is behind the latest advertising campaign for Hickey Freeman, the American men’s wear heritage brand, which Avery appears in. Its fourth-floor office space is sunlit and open, and is filled with young creative types in comfortable looking, but definitely expensive, clothes. Avery, in his double-breasted suit, is the closest thing the place comes to “Mad Men.” He has been spending a solid portion of his free time there lately. The ceilings are high and rows of photography books line one half-block long wall. It’s like a Hollywood back lot version of a 21st century ad agency. In fact, on the day Avery is there to preview the Hickey campaign, Rachel McAdams is there shadowing the company’s chairman, David Lipman, as research for an upcoming Brian DePalma movie.

Lipman greets him and, after some small talk, has the images on the television screen in front of three low couches.

“Everybody wanted to bail, and I just stood in and said: ‘This is what he’s about,’” says Lipman. The topic has returned to Avery’s Los Angeles arrest, which happened while the Hickey deal was still in the works.

“He stood up for what he believed at that moment, whether it be authority, or anything,” Lipman, who like any good ad man has a habit of speaking in epiphanies, continues. “Police can’t come into his house like that. And he just stood up for it and that’s the man we want. I stood firm by it. I stood firm by Kate Moss when she was in trouble....At that point I didn’t know Sean well enough to have personal feelings because we just met. I knew my client better than I knew Sean, but I knew it was the right thing for them.”

Avery inked a deal after the dust settled.

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