Staying the Course

  • Jim Brady looks out at Casco Bay from the waterfront near 58 Fore Street, where he is partner in a major development.

  • Brady and his wife, Julia, in the lounge at the Press Hotel.

  • Brady wears his silver medal from the 1992 Olympics in Barcelona.

  • Sailboats wait for sailors on Casco Bay.

Under sail and ashore, Jim Brady’s passion propels him forward.

On a blustery, rain-whipped day in November of 1999, Jim Brady was sailing in the Hauraki Gulf off Auckland, New Zealand, when he noticed something was wrong with his boat. The tactician on the crew of Young America, the New York Yacht Club’s challenge team for the 2000 America’s Cup, Brady was in the stern of the 75-foot boat when he saw that the bow was much too high in the air. “We had just tacked and there was this explosion that sounded like a train wreck,” he says. “It took a second to register, ‘Oh my god, the boat just broke in half.’”

Brady and the rest of the 17-person crew jumped overboard and were quickly plucked out of the stormy water by support teams. No one was injured, but even though the crew of Young America had a spare boat, the team never recovered, and for the first time in its history, there was no American boat in the America’s Cup that year. Others might see this as a devastating disappointment, but not Brady. Over the course of a sailing career that began when he was a teenager in Florida, he had already achieved greatness, winning a silver medal at the 1992 Olympics in Barcelona, and multiple national, European, and world championships. He also met his wife, Julia, a sailor and a 1992 bronze medalist, during the Olympic trials. The 2000 America’s Cup was his second; he had served as navigator on Dennis Conner’s Stars and Stripes for the 1995 race. Most of Brady’s victories, however, were in a broad class of boats called one-designs, which require two- to three-person crews. “The America’s Cup is about research and technology; because of that it’s really a big game of money,” he says. “The sailing skill it takes to win in a one-design, when everybody has the same equipment, is very different and much more respectable from a sailing talent perspective than winning the America’s Cup.”

Those who know the boyishly handsome, charismatic Brady as a prominent Portland real estate developer may be surprised to learn of his past as a top-ranked sailor. In fact, it was his Olympic teammate, Bangor native Kevin Mahaney, who suggested that if Brady wanted to transition out of professional sailing, he should join him at his real estate and hotel development company. When he was named Rolex Yachtsman of the Year in 1990, Brady told the Baltimore Sun: “I look at a sailing campaign like a business, where organization, focus, and direction make the difference.” It was a prescient statement, given the business success that has echoed his wins on the water. “One of things that I really like about sailing is that it has this very competitive drive,” he says. “Everybody is pushing and doing everything that the rules allow to win that race. But when you get ashore there is a lot of camaraderie. I like being able to push the limits and drive an effort toward a goal. But then also have some fun.”

Translated to real estate development, Brady’s idea of having fun is being involved in meaningful projects. “I’m not the guy who is going to build a fancy spreadsheet,” he says. “I’m more into the design side and creating something that is really interesting and engaging to the public and the community.” As an example, he cites the Press Hotel, which he developed in the former home of the Portland Press Herald across from City Hall. While others collaborated on the project, it was Brady’s vision to tie the design of the boutique hotel to the building’s history. “I put the interior design firm I hired on the starting block and said, ‘Head that way,’ and they took it and did some really creative stuff. The headlines on the wall covering in the corridors—that was one of their ideas; so was the typewriter lettering kind of falling off on the carpet.” He knows the design details appeal to guests because he reads the hotel’s Trip Advisor reviews on a daily basis. “I focus on what was the experience or memorable item that caught somebody’s attention and made them want to write about it,” he says.

There has been plenty of ink devoted to Brady’s latest effort, the development of 58 Fore Street, a 10-acre industrial site on the waterfront at the foot of Munjoy Hill. The multi-phase plan for the former home of the Portland Company includes housing, a hotel, retail and office spaces, a marina, and a public plaza offering broad access to the water. “It’s been a challenging project; I think that’s a fair statement,” Brady says of the ongoing legal fight brought by a small group of the property’s neighbors. “They continue to basically battle us at every turn, and that’s cost us dearly on time. But it has the ability to really be the crown jewel of Portland.” Brady and Julia, a group strategy director at the VIA Agency, recently moved from Yarmouth to Munjoy Hill. He makes a habit of stopping in at the Hilltop Coffee Shop, hoping to win over those who have not been in favor of his plans for 58 Fore Street. “I often walk up and say hello to the folks who are outspoken against the project,” he says. “I’d rather try to wow them with friendliness and respect than the opposite.”

Not long after the 2000 America’s Cup disaster, the Bradys relocated to Maine, where they opted for the ease of a powerboat, allowing them to explore Casco Bay with their two daughters, now teenagers. “I’ve always told people we don’t have a sailboat because we’re very fortunate to have some wonderful friends who do have sailboats,” Brady says with a chuckle. Having lived all over the world for his sailing and business careers, he has put down roots in Portland and is devoted to seeing the city thrive. “The more office spaces and places people want to live we can generate, the more the wonderful coffee shops and art galleries we all want in our neighborhoods can be supported,” he says, adding that hotel rooms, which help draw tourism dollars, are a vital part of the mix. “I’m a big believer in that you always need to think about the future.” Brady’s racing days may be over, but he’s still keeping his eye on the finish line.


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