For nearly two decades, Dave Perry the Match Racer was in hibernation. After winning the Prince of Wales Trophy (US SAILING’s match racing championship) in 1982, and the Congressional Cup in 1983 and ’84, and just missing the 1984 U.S. Olympic Team in the Soling, Perry focused his energy on his family and his career as the athletic director at Greens Farms Academy in Westport, Conn. He fed the beast with the occasional team race, a few keelboat events, and his popular rules clinics. Last spring, with his youngest child now off to college,Perry, 52, decided to see if his fangs were still sharp. So he retired from Greens Farms, landed a gig as the rules advisor for Victory Challenge, and started training for another run at the trophy he first won nearly a quarter century earlier.It came down to the final race against Brian Angel in the finals of the 2006 POW. How did it turn out?I wouldn’t say I was nervous but, man, it was close and I really wanted to win. I had confidence we had the better team. I had Terry Flynn sailing with us and he’d just won the J/22 North Americans. We were on Eagle Mountain Lake, really shifty, really puffy, and you had to go the right way. Chris Museler was just on fire; he didn’t miss a call. The last race he said, ‘Dave, we want the right side off the line.’ We split for about two minutes, a long time in match racing. We were leading by about 20 boatlengths at the first mark. We sailed into a hole on the run and he brought the breeze down with him and we were bow to bow going up the second beat. Chris said, ‘We want the left.’ We split again, we got the breeze, he never got it, and we were a third of way down the run before he got to the mark. That was the nature of the racing.How did it compare to your first win?In 1982, we were just coming to the scene, we wanted to get to the Congressional Cup, which we got to as a result of wining the POW, and we won the Con Cup in 1983 and ’84. We wouldn’t have been invited if we hadn’t won the POW. So it was probably more important for my Olympic effort. But I was a pretty happy camper [this time]. You know what else is great? That somebody could come back and compete at a high level 24 years later. It really is a sport for a lifetime.Most of our readers probably know you through your books. How did those come about?I’m a teacher at heart so when I was doing my racing, I wrote my column Winning in One-Designs for your old magazine, Yacht Racing & Cruising. I did that from 1979 to 1982 and then put those columns into a book. The rules have always been something I’ve been interested in. The more I taught them, the more people said, ‘Hey that’s really helpful.’ So I wrote the first version of that book in 1984. Every four years, when the new version of the rules comes out, I update it. [Perry also wrote a book of rules quizzes.]But that wasn’t your primary job. You just retired from Greens Farms Academy. How were you able to do that at 52?As my wife reminds me, I haven’t retired, I just retired from that job. Twenty-one years was enough. I really missed sailing and racing. I turned 51 and said if I want to get back in, in any way at all, I have to do it now.How did you become Victory Challenge’s rules advisor?I put the word out to a few people that I’d be coming on the scene again and I needed to make a living sailing professionally, coaching, helping out. Brad Dellenbaugh, the chief umpire for the America’s Cup, was sitting in Magnus Holmberg’s office this past May and Magnus said to Brad, ‘Hey do you have an idea about who could be a rules advisor?’ Brad said, ‘You should call Dave.’ So he called me and said, ‘Would you be interested?’ We decided I’d go over and work with them [for Act 12] and see if we were a good fit. They were great. So now I have a job through the end of the Cup.What are your primary responsibilities with the syndicate?I handle the racing end of the rules. It’s amazing how many rules there are for a race with just two boats. You’ve got the Racing Rules of Sailing; then you have the ISAF Match Racing Call Book, which the umpires follow; then the America’s Cup umpires have their own call book; then you’ve got the deed of gift; the protocol; the AC class rules; the notice of race; the sailing instructions. There are literally about 7 major documents that pertain to the racing, and I have to be on top of all of them. Now that the rules are your life, do you enjoy them as much as you did previously? For some reason I have this insatiable enjoyment of trying to figure out what rules say and how to apply that to your racing. Knowing the rules is a means to being a better competitor.The rules sometimes get a bad rap. Do you think the average sailor has enough respect for the rules?People respect the game. When they’re out there playing the game, whether they know it or not, they’re following the rules. A lot are obvious: port-starboard, windward-leeward, room at the mark. Where it gets into trouble is when some sailors start to yell at other sailors, yelling rules and starting to use them as verbal weaponry. I have no respect for that either. Two of your teammates at Yale, Steve Benjamin and Peter Isler, have made a nice living out of sailing. Stan Honey found a lot of success as well. Ever wish you had followed a similar path?I had no interest in making sailboat racing my career. We took our best swing at the Olympics in 1984, came as close as you can get to making the Olympic Games. Then Robbie, Ed, and Rod won the [Soling] gold without having to sail the last race. I happily went into another lifestyle and now I’m happy to be back.You mentioned wanting to do some professional sailing. Have you?I had a chance to do some Farr 40 sailing this summer. I did the Chicago NOOD and just loved it. I wish I could do much more of that. I love sitting on the back of the boat behind the driver, having no responsibilities other than looking around and playing the game. I’m not a speed guy, I’m not going to tell you how to tune your rig, or recut your sail. I’m a game player. What’s your arrangement with Victory?I am basically 10 to 12 days a month until March, then I move over full-time and stay until we get the job done. But even now, with the Internet, every day I’m doing something for them.Victory has ramped up aggressively over the past few months. Is the team on the right path? Is there enough time?I think things are completely moving on the right track. I am completely impressed every time I go over there. Neal McDonald’s sitting next to me in my office, Morgan Larson’s on board. The synergy on the base is at a really high level. With Red Bull as a sponsor they seem to be able to afford to do some things they couldn’t do before. Plus Red Bull has brought some of their [Formula 1] technicians on board. Of course there’s not enough time; we could use another three years. That’s the difference between the teams that are more successful; they’ve been at it longer. But we’re growing fast.