Chicago to Mackinac Sailboat Race, Valkyrie 2005
by Tom Trimmer

I had one arm wrapped tightly around the shrouds (taut cables holding the mast in place) as the sailboat careened through the darkness like an untamed beast over and through wave after massive wave. My position up on deck near the front of the 40-foot sailboat was a bit precarious I thought, so precarious that I had clipped a line from my harness/lifejacket to the safety tether running the length of the boat before venturing out of the relative safety of the cockpit. My left hand strained to control the spinnaker sheet, as I every so often glanced at the roiling water ripping by me at an incredible fourteen knots, though we had never had the boat going faster than ten knots before. When I needed more tension on the sheet I would turn back towards the cockpit and scream “TRIM TRIM TRIM!!” over the howling wind as I watched our largest spinnaker and tried to keep it under control, working with the helmsman and the other men on our watch to keep the entire boat from going over onto its side. We had been unable or unwilling to bring our biggest spinnaker down as the wind built from a relatively benign ten knots to an exponentially more forceful, raging and gusting twenty-three knots as the night wore on. I watched with a detached curiosity as the boat rammed straight into the backside of a particularly huge wave, burying the entire bow under water, almost all the way back to me. It brought the boat to an abrupt, near-stop. When this happened, all the force on the huge spinnaker was no longer driving us forward, and instead the boat was quickly pushed nearly horizontal as I released the sheet—just in time to save us and to the frantic screams of “BLOW THE SHEET!!! BLOW THE SHEET!! BLOOOW THE SHEEEET!!” from the cockpit. “IT’S BLOWN!! IT’S BLOWN!!” I screamed back, somewhat desperately hanging on as the deck went vertical. The giant spinnaker popped and cracked in the wind, uncontrolled and making what sounded like gunshot after gunshot in a wild, incredible, fearsome display of raw, unharnessed power.

Big Jon Martin (left) and Jon ‘Mad Dog’ Madorsky enjoying the ride down the straits of Mackinac.

The trip had started 36 hours before in Chicago as our crew of eight onboard our J120, a 40-foot raceboat, had begun the race on a beautiful sunny day off the coast of downtown Chicago. Eight men together for fifty hours in a space smaller than my apartment over 330 miles of open water, for better or for worse, come what may. I had known it would be an adventure and had worked hard on the boat in the Wednesday evening races and shorter distance races throughout the spring and summer in an effort to secure an invitation to this great racing tradition. Doing the Mac had been a dream of mine for many years, and was finally coming true.

Our crew was a great bunch of guys, all low key, laid back, but hard working and with a winning mindset and expectation. The perfect combination as far as I was concerned, and I was proud and excited to be a part of the team. I had grown up sailing with my father and while sailing and racing isn’t my biggest passion in life, it is something I enjoy immensely. There’s nothing quite like being out on the open water, no land in sight, moving under the power of the wind alone, just you and your friends and the vessel that is your temporary home for the duration of the trip. No matter what happens, you have nobody to rely on but yourself and your teammates. Storms, broken equipment, emergencies, illness, injury, anything and everything out on the great lake is your responsibility and yours alone. No 911 calls, no cabs, no button to turn it off if you don’t like it. You can’t say, “Ok I can’t take any more, let me off.” You and your microcosm of society have to deal with whatever comes along until you get back to land. That’s a big part of the allure for me, the freedom from rules, from the ultra-safe society we live in. The chance to prove yourself and see how you act in situations demanding courage and quick thought, possibly desperate survival situations.

The author trimming the spinnaker.

Throughout the first day and night things went smoothly for us. We did pretty well against the other boats considering it was our first Mac as a team. We managed to be in about the middle of our group of boats as dawn rose on the second day. We learned this from the radio and from the few boats that we would see every so often with our binoculars. Several hundred boats were competing, but often only one or two were visible. The lake is immense, and my appreciation for its size and beauty grew exponentially during the race.

As the second day passed, sunny and with great wind blowing us at near our top speed up the lake, our spirits were high and everything was going well. Each evening we had warm meals we served to each other, and during the day there was plenty of sandwich meat and food to snack on. We worked as two teams of four, changing watch every three to four hours throughout the day and night. I felt surprisingly well rested and alert considering the sleep schedule. It seemed like a fairly regular occurrence where my team would be off-shift and sleeping soundly down below when the call would come out “all hands on deck!! Everybody up!” and we’d scramble around, sometimes in the dark to get our gear on and help with whatever situation, usually just changing a spinnaker or sail.

Going into the second evening, all was well and we had our largest spinnaker up in the late afternoon, with the wind blowing a comfortable ten knots. One guy would be up on deck, with the spinnaker sheet in hand, and a grinder would be on the winch, waiting to help work the winch should the trimmer ask, and bring the sail in tighter if the trimmer deemed it necessary to maximize our performance. We had our warm meal then changed shifts back and forth a few times. Our turn came again a little after midnight. As we came into the cockpit, I noticed the wind had built and we were going extremely fast, with the huge, light-wind spinnaker still up. Jon Madorsky and I were trimmer/grinder partners. Generally we would switch positions every 45 minutes or so as both jobs can be tiring. It looked pretty grim with the wind and six to eight foot waves, and the thought of being the trimmer way up on deck was intimidating to both of us. “Do you wanna go first?” “You wanna go first?” we both asked. “I don’t care” “doesn’t matter” we said… and I volunteered, secretly relishing the danger. I clipped into the tether line and stepped up out of the cockpit with some trepidation. As I made my cautious way forward with the deck pitching and heaving beneath me, I said hello to Big Jon Martin, the current spinnaker trimmer I was relieving. He greeted me with a huge smile and was completely at ease, talking to me as though we were sitting in his living room watching football. “Here you go,” he said as he handed me the extremely taut line. “I hang on to the shrouds. Keep it over trimmed—no need for any extra performance. Have fun!” And with that he was gone and I was left alone with the water rushing past, the huge waves, a rolling deck, gorgeous stars, the howling wind, and the line controlling the giant spinnaker held tightly in my hand.

The Valkyrie crew (off-shift guys relaxing) reaching down the Straits of Mackinac only several hours from the finish.

We raced on like this for probably another thirty minutes or so, riding the thin line between maximizing our boat speed and insanity that it takes to win races. We were getting ever closer to crossing the line into insanity and were barely holding it together. We had plowed into some waves as I was trimming up on deck, and it had slowed us some but not disastrously. It was an incredible feeling to be up there, hanging on to the boat with one arm and controlling the massive spinnaker with the other, pushing the boat way beyond anything we had ever done before. We were out there alone, and I was up on deck by myself—the water speeding past me as we sliced through it like a speedboat, throwing big plumes of spray off the bow as we screamed our way north. I had the time to enjoy the stars and appreciate where we were and what we were doing, truly enjoying the experience. Then we went surfing down the back of a particularly big wave, and picked up so much speed we plowed right into the back of another wave, bringing us nearly to a standstill. All the power that had been driving us forward now threatened to blow us over in a split second as I instinctively let the spinnaker sheet run through my hands. The boat was already nearly completely over before the pressure went out of the spinnaker, allowing the boat to right itself somewhat—but now we were in a truly desperate situation. The spinnaker was now whipping about in wild abandon, this way and that, cracking and snapping like shotgun burst after shotgun burst. Guys were scrambling up into the cockpit from down below, and with the mainsail still up we were still moving. The spinnaker needed to be taken down, and taken down quickly. Every so often it would fill a bit and the boat would lean way over as we all grabbed something and tried to hang on. The wind didn’t abate at all and we could hardly hear each other over it, having to scream every word. There are many different spinnaker takedown routines, and we had gone over many of them and practiced the emergency ones—but it is all very different when you are faced with a true emergency, blasting wind and unruly waves and darkness all converging. After a couple botched attempts at getting it down and another few near-capsizes, we had no idea what to do and were all fairly shaken, still having averted disaster but barely—and with disaster looking more and more imminent. Our most experienced crewman, in a bout of panic yelled “WE ARE SO...!” This did nothing for our cause and certainly didn’t calm anybody down. I don’t remember exactly what happened but we eventually succeeded in getting the spinnaker behind the mainsail, which sapped some of its strength long enough for us to get it under control and down the companionway.

Some of the raceboats rafted up in Mackinac Island Harbor.

After this we all took a bit of a breather—but it shook us up for the next several hours. In a conservative move, reflecting on our recent near-catastrophe and seeing lightning far out on the horizon, we replaced our absolute largest sail with our smallest storm jib. Boat after boat passed us through the night and into the morning until we got ourselves together and back into the race mentally. We rounded some notoriously dangerous rocks and headed east down the straits of Mackinac, on the home stretch and threw up another spinnaker. We were again doing full speed, jibing back and forth down the straits, glorious sun shining, helicopters flying by and taking pictures, and really enjoying ourselves, though we were again in a very strong wind and pushing our boat to the edge. Then… all the sudden the boat was careening out of control—the spinnaker began pulling away from the mast at the top. Farther and farther—two feet, four feet, eight feet away. What was going on? The boat lurched back and forth as the spinnaker pulled us wildly left and right, again threatening to capsize us. John Moore, the owner, was at the wheel valiantly fighting to maintain control and yell out directions. The inside of the halyard was coming undone from the sheath—meaning the clutch was holding the outside of the line but not the line itself. A small panic ensued but we managed to get this spinnaker down with a couple wry jokes about our luck and our poor beat-up boat. Up went one of the few sails we had left, and we limped into Mackinac Island Harbor, exhausted, elated, ready for a beer, and proud of our accomplishment.

Tom Trimmer has been sailing since age 10, learning on Y-boats at Orchard Lake Yacht Club outside of Detroit, Michigan. His family purchased a 26 foot tub which we owned with another family for about five years before upgrading to an Ericson 38 as a family. Tom purchased a Catalina 22 upon moving to Chicago, then two years later upgraded to an Ericson 28, which he keeps today at Monroe Harbor in downtown Chicago. He hosts bachelorette parties on it during the summertime.

He’s raced many weekend port-to-port races out of Chicago, the Port Huron to Rogers City double-handed in 1999, and has done some cruising in the Virgin Islands, the North Channel of Lake Huron, and some racing on Nantucket Island. His other interests include rock climbing, mountaineering, skiing, world travel, and kayaking.