I was at sailing camp on the West River of the Chesapeake Bay almost a decade ago and he was the more experienced of the instructors. He was a short but large man with thick leathery skin and hard blue eyes with a way of asking for things in such a way as they’d get done and teaching skills in such a way as they were learned. The moment he walked onto a boat no one called him Jack any more, he was Skipper, and it was just so natural to call him that. So, one day towards the end of our trip around the bay at a campfire, he tells us this story of how he learned not to sail.
His plan was to sail across the Delaware Bay to Ocean City where he would meet his wife who would drive the more circuitous route. The story begins with him getting a late start because of something foolish I don’t remember, but he figured that the wind was good enough that if he hurried he would still be able to make good time. So he drove his 20 foot sailboat to the ramp closest to his house and, after quickly checking everything, backed it down the ramp. However, he overlooked his brand new rudder, which was down, and it abruptly shattered as he lowered his boat into the water. I can’t imagine how that sound must have felt, but when he reconnoitered he figured he could still get a nice cruise out of the day and attach his outboard motor where the rudder used to be.
It took a while to collect the remains of his rudder and to run to get the motor, so he was a bit hurried as he attached the thing to his boat, but he got everything together and headed out. Just after he was underway, he realized that, while still mourning his rudder, he had not properly screwed in the outboard motor and that it was shaking itself loose. He had also left the tools necessary to properly attach it in his truck and so he figured that the best he could do was get a good strong grip on it and manhandle the boat across the bay. This worked pretty well and he got just a bit more than halfway to the other side in this fashion. However, just as he was figuring he had gotten the hang of how to keep the motor on the boat and was beginning to enjoy his cruise, a wave caught him unawares causing him to overcompensate with the motor, leaving it to fall right overboard. He still had his handle on it and so reflexively he manhandled it right back onto the boat. Still running. Across his lap. At which point he dropped it and it went right back into the bay.
Now he was in trouble. Thankfully the propeller didn’t hit his femoral artery, but it cut deep and he was losing a lot of blood. He was also right in the middle of the bay, with no rudder, no motor, and no way to call for help. This was bad. The only thing that was really left for him to do was to propel himself with his mainsail without the rudder, which is doable but very non-trivial. He managed to get to the other shore this way and it was getting into the late afternoon, well after his wife knew to expect him, but he figured that he was on a roll, that abandoning the boat on the Delaware shore could be risky to it especially as he would need emergency medical attention, and that he was indeed almost there. So he soldiered on down the coast to Ocean City.
Somehow he made it, and it was just starting to get dark. Now the way into Ocean City by sea is under the same bridge that most people take to get into Ocean City by land, and a portion of it is a drawbridge for exactly this reason. Now our hapless Skipper had to wait in line with everyone else as he struggled to keep the boat under control without moving forward and without a rudder while missing a sizable amount of his legs. Once it was finally his turn to go under the bridge, he miscalculated the approach, which didn’t necessarily have a solution, and ended up drifting into the gears of the drawbridge apparatus. The moment his mast hit the gears, it lodged itself in there and immediately guided gallons of thick green black motor oil right down the sail to coat it, and much of the boat, in the slick slippery stuff. Now he was in trouble and there really wasn’t much he could do other then yell back at the angry bridge operator in the booth, who was also largely impotent to help, until he pulled out the most important piece of safety equipment one can have on a boat.
He went to his small cabin and grabbed a case of beer and a line, and he held them up to the growing pile of boats behind him waiting to get home for the night. Pretty soon a dinghy with a couple of thirsty guys wordlessly came forward, took both one end of the line and the beer, and dragged the poor boat out the other side of the drawbridge before dropping it just as quickly. Poor Jack then still managed to get his boat through the bay, oil on the sails and all, to the marina where he had reserved a slip and marched up to the booth to figure out which one was his. Apparently, when he walked up to the desk, the tall scrawny kid who was left there for the evening had the gall to tell him that they had given away his slip for the evening, as he was hours late, and that they had no more left of the right size. However Jack, now exhausted, covered in blood and oil, and in serious need of medical attention wasn’t taking no for an answer. So he grabbed the poor kid by collar, pulled him down to eye level and made sure he understood that a slip would be found. It turns out there was still a slip available, of the largest size, the kind meant for big luxury yachts. So Jack then piloted his boat over to the slip drawing awed silence from the black tie cocktail party going on in the slip next door. You can imagine the sight, a big burly bearded man black and red with blood and oil guiding his vessel into the slip with a mainsail dripping black with the same oil past tuxedos and gowns, then wordlessly tying up his boat and going about his business. With his boat safe, Jack then found a payphone to call his wife and the EMS.
Apparently his scars were placed just unfortunately enough that he couldn’t show them to this group of minors in his care, but his wife happily vouched for their existence and severity. She also clearly had not forgotten the worry of him not arriving and then that call and then the surgery, or the expensiveness of the rudder and outboard motor. However Jack told us that he learned a lot that day, about the foolishness of half measures, the value of persistence, and the importance of paying attention to whatever it is that you are doing.