The Afterlife of Jim Brady

Professional sailor Jim Brady was at the peak of his career when he tacked and joined the corporate world, but lessons learned on the racecourse have done him well.

Jim Brady
Having long stepped away from professional sailing, Jim Brady now owns and manages hotel properties in Portland, Maine, but he’s not ruling out a return. Nicole Wolf

Jim Brady had the kind of sailing career that ambitious young Optimist sailors dream about—world champion, Olympic medalist, America’s Cup tactician and Rolex Yachtsman of the Year. But these days, you’ll find him pottering with the family in his picnic boat on Portland’s Casco Bay.

Brady grew up in Florida, son of an Air Force pilot and colonel. “We were fortunate enough to live on the water in Florida, so I always had an interest in being not just in the water, but on the water as well,” he says. It was his father that introduced the family to sailing with the purchase of a Hobie Cat when Brady was 8 years old.

“One thing led to another, and I guess this was probably about 1978 when the J/24 came out and was starting to become a popular boat. A guy named Mark Ploch, who was a top 470 sailor at the time (now owner of Doyle Sails in New York City) had just moved to town and was starting a sailmaking loft. He approached my dad and said, ‘Hey, how about you buy half of this J/24, and I’ll take your two sons as my crew and help teach them how to be good sailors?’”


It was a fantastic opportunity for the young Brady. Together with Ploch they won the J/24 Midwinters in their first year in the boat; Brady was just 15 and living the dream. “I also bought a Laser and went on to the youth national championships. The best I did there was second. I kind of jumped into it with full force between the J/24, the Laser on my own, and at the same time, leading up into the 1980 Olympics, I started sailing in a Soling and ultimately joined a crew with Ed Baird as the helmsman and Steve Calder as the middleman.”

The United States boycott of the Moscow Olympics put paid to that campaign, but it was still something to be competing for an Olympic berth in your teens. A lot was down to Clearwater, a hotbed of competition at the time. Apart from Ploch, Vince Brun, Peter Branning and Steve Calder all lived locally, and both the guidance and the competition were excellent.

“I was very fortunate, frankly, to be tutored by Mark Ploch, and then by Ed Baird and Steve Calder,” Brady says. “What I learned from each of them was that if you wanted to win, you had to put in the effort—training, practicing and preparing for the race. It sounds simple, but they believed more time spent efficiently in the boat ­sailing and working on performance or mark-rounding or maneuvers would give you the confidence to out-sail the competition.”


The next step was clear to Brady: college sailing. Attending the College of Charleston in South Carolina, he was an All-American in his sophomore year but never graduated. He took a semester off to compete in the J/24 Worlds in Japan in 1985 and after that got an offer of full-time employment from UK Sails. He thought, “I’m trying to go to college to get a decent job. This seems like a pretty good job, so why go back?”

Not everyone agreed it was a good idea. “My dad has a Ph.D. in education, so to drop out of college and do this was probably not one of the things he would’ve been in favor of ­initially,” Brady says.

Success, however, changed things. “My mother came with me to the Pan-Am Games, and it was the first time she realized, ‘Wow, you’re actually pretty good at this stuff.’ From that time forward, I think I had a lot more support for doing what I was doing, which was a pretty nontraditional path.”


By the mid-’80s, he was ­driving, already one of the top sailors in classes like the J/24, in which he won the Worlds in Dublin in 1990. Brady also broke into the bigger offshore classes racing aboard Abracadabra alongside Ploch. He won the One Ton Cup in 1991 with David Clarke’s Vibes, a Bruce Farr design that was managed by Geoff Stagg, who then got him involved in more top Farr programs. He also moved to North Sails, and his career started to peak.

“I had a pretty good year and probably hit more than a dozen major championship ­regattas and won all of them. It was one of those things where the stars aligned,” he says. His 1990 Rolex Yachtsman of the Year selection acknowledged this purple period.

Meanwhile, Olympic sailing was about to come back into focus. After sitting out 1984 while he was at college, Brady and Baird made a late run at the 1988 trials and came in third. Kevin Mahaney had been fourth, and a few weeks later he got in touch with Brady and suggested they start early and do it right. The pair picked Doug Kern as the middleman and went sailing, eventually winning the US Soling trials and going all the way to the gold-medal match, where they met Denmark’s Jesper Bank.


“We made a couple of mistakes in the finals, and having dominated really the whole week, the whole Olympic gold-medal dream faded away for us in the last 30 minutes of the week of glory in Barcelona. Our biggest mistake was on the last beat of the first race. We were several lengths ahead and had pushed him early to the starboard-tack layline. Because we were easily laying the mark, we decided not to go back to tack on him one more time. He got a puff three lengths up on our hip, and we sailed into a hole, and that was that race. We were very fortunate to win a silver medal but, frankly, very disappointed that we weren’t able to have ended up with the gold, which was our ultimate target.”

Despite the ­disappointment, Brady put the dream aside. “I felt like I had kind of been there and done that, even though we didn’t win the gold. Kevin was moving on and thinking about doing the America’s Cup, and I had been doing more of the big-boat sailing because of the successes and name recognition from being the Rolex Yachtsman of the Year and an Olympic medalist. It gave me a real entrée into writing my own ticket on the big-boat side. Shortly after the Olympics in 1992, Dennis Conner approached me and asked if I would consider doing the America’s Cup program with him on Stars and Stripes.”

Brady checked in with Mahaney on his Cup plans and was told it was too early to make any kind of commitment. Mahaney’s advice was to go with Dennis. “So, I ultimately left Kevin and signed up for the Stars and Stripes program to do the America’s Cup in 1995. I remember very clearly coming off the starting line in race one in San Diego, and we were in a pretty even start. I would’ve said the Kiwis were just a boatlength and a half up on our hip. They sailed the same speed and about 3 degrees higher than we did the entire time. They just climbed off of our hip. And I thought, ‘This is going to be a really long week.’”

They went down 5-0 to the New Zealanders.

Afterward, Brady led a Mumm 36 program that would eventually initiate a dramatic change in his life. “We put together what I think was really one of the best sailing teams or programs I’d ever been involved with. We had a great boat. We had a great team. We had a great sponsor and were fortunate enough to do quite well in the Mumm 36, from the Admiral’s Cup to winning the Mumm US Nationals and European championships.”

Then the 1997 financial crisis hit Japan and the sponsorship dried up. “When things went bad in Japan, some of our sponsorship…the deal really kind of blew apart. I ended up having to fund the end of the program. The money never came through, but we had already made so many commitments to the sailing team that we decided to go do the SORC and Key West Race Week.”

It was a remarkable decision by Brady to underwrite the commitments he had made to his team—at his own expense—and the personal cost caused a serious rethink. “It made me really think hard about the fact that I had put a lot of eggs into one basket with this particular program. I was debating whether or not I really wanted to just think about something different.”

Brady’s wife, Julia Trotman Brady (Olympic bronze medalist in 1992 and Rolex Yachtswoman of the Year in 1993), was at Harvard Business School, and the couple was living in Boston, where Brady reconnected with Mahaney. Mahaney’s reaction to Brady’s career dilemma was to offer him a job with the family business, managing and ­developing hotels.

“So, I decided, ‘Well, what the heck? I’ll take the next six or 12 months and kind of see what this is like.’”

They raised some money, bought a rundown hotel, and successfully renovated it. “I stuck with Kevin for about a year, and then we didn’t have any deal flow in the late 1990s. I literally was making minimum wage. I was going to get some equity on deals we did, but if we had no deal flow, there was no upside. So, I left and went to work at Starwood Hotels and Resorts for a little while.”

This did not go well. “It became really clear to me in a very short period of time at Starwood that without an MBA, yet alone a college degree, I wasn’t going to get ahead in that organization. No matter how smart I was or how talented or experienced, or whatever things that I could bring to the table, without an MBA, I wasn’t going to be ­listened to.”

Fortunately, sailing wasn’t quite finished with Brady. He got a call from the New York YC’s campaign for the 2000 America’s Cup, skippered by Baird. In some ways, it was a backward step to an old life, but it came at an auspicious moment. “Julia was pregnant, and I saw the writing on the wall that Starwood wasn’t going to work out for me. So, I agreed to join in the 2000 America’s Cup with Young America.”

While the family was in New Zealand, Mahaney came and stayed, and this time they developed a partnership that stuck. The family moved to Portland, Maine, after the Cup, and Brady started to work for Mahaney. “I ran the development arm of the company. And I stayed there until 2008. I kind of turned my switch off on sailing. I did it because I’m the type of person who wants to really ­succeed at whatever I do.

“Eventually, you say no so many times that the phone completely stops ringing. I haven’t heard from anybody in years.”

“I decided that it was time for me to really make a living, and I just really singly focused my effort on this. So, for eight years, we developed a number of different hotels, mostly Hilton franchised properties, where we would build ground-up hotels and operate them. I was responsible for both site acquisition, getting all the permits and approvals, the design, as well as the construction, right through to getting the hotel open.”

Life might well have continued on this path if it wasn’t for the early shocks of another financial crisis. In the summer of 2008, real estate was slowing, and Mahaney suggested it was a good time to take a sabbatical. “I took the summer of 2008 and decided to move my family to Italy, with the idea that we would just take one year, and I would come back. Well, the world fell apart within months of us moving to Italy, with the Lehman collapse in the fall of 2008, which pretty much put a squash to virtually all real estate development.”

He got a job consulting to a real estate group in Italy for the next three years, eventually returning to the United States in 2011 to put their daughters back into the American school system. It was at this moment that Brady decided to take the plunge. “I decided that I would hang out my own shingle and find some opportunities on my own.”

He found the old Portland Press Herald Newspaper building, dating back to 1923. “I thought, ‘Jeez, that could be a really cool hotel.’ The market was strong, and ultimately I took some really big risks at the time because we were still kind of just starting to come out of the recession, and nobody had a lot of faith going forward.”

The hotel opened in 2015, winning plaudits and awards, and Brady has now started a company to operate it as well. “It’s been the market leader by a big margin since its opening. We’ve acquired another historic building and just did a rehab of that, and my offices are now on the top floor of that building, and we broke ground on a new 135-room hotel, which is called Canopy by Hilton. We’ll develop it, own it, and operate that project as well. That’s also right here in Portland.”

While the last 18 months have not been easy for Brady, the hotel and the hospitality industry, he feels he’s continuing to weather the worst of the storm. Meanwhile, the Olympic medalist and former America’s Cup tactician has barely been near a boat. He has done a little J/105 and Swan 42 sailing with Glenn Darden.

Things might change, though. He had a day out with Terry Hutchinson, and then with Peter Holmberg’s TP52 program while they were training in Europe. “I’m looking for the right opportunities to get back out there and get back sailing,” Brady says. “It’s interesting, after you step out for a while, and the phone rings for a number of years. Eventually, you say no so many times that the phone completely stops ringing. I haven’t heard from anybody in years.”

Brady regards his time as a professional sailor at the very top of the game as a stepping stone to his life now. “I don’t think I could’ve shortcut and gone straight to real estate,” he says. “I learned an awful lot from sailing and also made a lot of great connections that were ultimately the key to my success in moving on to another industry. I feel like I made some great friendships, got to see the world, and really enjoyed the competition.”


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