Once upon a time, John Jennings was one of the best young racers in the United States. He never won the Sears Cup–the junior national championship–but he finished second, three years in a row, and as an adult, he’s won plenty of major events. You can find his name engraved a couple of times each on two US SAILING national trophies–the Prince of Wales and the Mallory Cup, the match-racing and fleet-racing championships, respectively. More recently, the mild-mannered 61-year-old chiropractor, from St. Petersburg, Fla., has taken charge of the International Masters Regatta at St. Francis YC, helped this year by crewmembers Phil Smithies, Ron “Hacksaw” Hyatt, and Rob Moore. I had the chance to observe Dr. Jennings’ style–and his transom–from a competitor’s boat last October on San Francisco Bay, and asked him to share his secrets.What are the main things you do to get the most out of borrowed boats?You have to have a real good crew and do enough practicing with them to get the sails up and down. That’s fundamental to doing well. Then it becomes “feel.” You trim the boat and move things around, and then just try to sail consistently and stay out of foul trouble. The object is to stay in the top 5 and not take any severe chances. In US SAILING borrowed-boat regattas, there’s always a dog boat, and if you can do better than the others do in that boat, you have a good chance to win. What adjustments do you make?Since you’re not allowed to tune the rig at the Masters, you have to work with the vang and the leads; and the crewwork has to be exceptionally good. Always go out early, and do sets, jibes, and takedowns to make sure everything works. It’s also important to check out everything you can. In this regatta, we sent Hacksaw up the mast every day to look things over, and one day he found one of the pins in the jib halyard furling gear was coming out. What’s in that regatta bag you carry?I always bring a ditty bag to a borrowed-boat regatta with telltales and tools so I can fix what I need. In the bag I also have a few shackles, a couple little blocks, and some Kevlar line. It’s paid off many times. In this regatta we used the Kevlar to tie a bullet block on the outhaul because the internal purchase wasn’t working. If at all possible, I like to return the boat to its owner in better shape than when I borrowed it.You mentioned leads and vang; were these key controls to finding J/105 boatspeed in the regatta’s moderate to windy conditions? **Jib leads were very important–we moved them one or two notches back, maybe up to 3 inches, in heavier winds and forward in lighter. The other real trick is getting the leech of the main right in heavier conditions. We used quite a bit of vang to bend the lower portion of the mast to take low-draft out, and of course we also bent the mast using the backstay. What you do depends on the sails you’re given. Another way we got extra speed was that I worked my own mainsheet upwind and put every member of the crew on the rail so the weight was out as much as possible. That’s something I’m used to from dinghy sailing, and something most other crews didn’t do.Racing along the Cityfront, in or out of the current, is a challenge. What was your general strategy and how did you approach your starts?We stayed away from trying to get the perfect start at the pin. To go for it when the current is with you is always going to be dangerous. We were probably a third of the way up the line when the pin was favored and, in the last race, when it wasn’t favored, we started at the committee boat. Having some local knowledge with Rob aboard definitely helped, but I also paid attention to the 5 to 10 degree shifts. Rob and I didn’t always agree, but because I’ve sailed there quite a few times now I have a better idea of the currents and felt there were times to take advantage of the shifts, not just the current.What are your fundamental principles in tactics and where did they pay off?I always try to sail consistently. We ended up a couple of times in the back of the fleet–once because we got held up into a corner on a run and another time going into the leeward mark with the current against us we got blanketed–but by not normally going to corners and by keeping the boat going well we found our way back to sixth at least. It had a lot to do with the crew. Another thing we were doing was cross-sheeting the jib, which got the weight farther to windward; we used Hacksaw, who’s light and quick, to reload the leeward winch. **What kind of input did you like to receive from your crew?They talked to me about waves and what they saw on the water, where the wind was, and the puffs that were coming. I don’t mind the chatter, as long as what they say is really there and happening! Ultimately, the final responsibility is mine; I do most of my own tactics in a situation like this. What was the key to winning this year’s regatta?I was very happy to win it last year and this year things worked out very easily. I don’t know that you can count on winning. The boats sometimes vary in speed, and the competition is always good. There’s probably more sportsmanship involved in this age group than in some of the younger generation because we sailed with different rules for so many years. I think the rule changes that were supposed to be simpler are not simpler and they lead to aggressive sailing to the degree that nobody has any idea, when they go into the protest room, what’s going to happen. Before you always knew there was an onus on somebody and that helped. The best thing you can do is stay out of the protest room, and that’s the way it worked for everyone in this regatta.Any help from lady luck at a critical moment?Definitely. You have to have a little horseshoe in these things. A couple of times we picked up somebody with a boat not quite as quick as ours or we picked up a couple shifts when people overlaid the weather mark in the current. We’re not used to that kind of current in St. Petersburg so we had to be really careful.Why do you enjoy borrowed-boatregattas so much?I love small-boat sailing in all sorts of boats. I’ve sailed Stars and FDs, and used to own Lasers, Snipes, Windsurfers, J/24s, Thistles, and Lightnings. But at these regattas it’s all about your sailing ability, not what you can do to a boat. Everybody has to overcome the same problems.