On any given weeknight at the windy city’s eponymous yacht club, jovial and windblown crew from the evening’s beer can races spill into the club’s expansive lounge and belly up to its L-shaped bar. At the far end of its short dogleg, next to the exit door leading to the club’s parking lot, is one of Chicago’s most celebrated sailors, holding court in what’s known as “Tom’s Corner.” Current and former crew, friends, and foes, parade past, briefly engaging him for an opinion, a joke, or maybe even a story. During pauses in the procession he guzzles a Miller Lite and puffs on a chubby, smoldering cigar.
That damn cigar.
The scene, albeit with a change of scenery, has been much the same at regatta tents and bars in Miami, Key West, Mackinac Island, and anywhere else to which Tom Neill and his cavorting Nitemare entourage have traveled. Through equal parts competitive sailing and frolicking, Neill and his extended sailing family have become the stuff of legend-the sort of team that everyone wants to be part of. And for better or worse, this self-described truck driver and his raceboats have become synonymous with Chicago sailing. Some even say Nitemare, and by extension, Neill himself, is Chicago sailing’s personality.
It’s been a reputation long in the making, and Neill, now 58, has been at the sport for decades. At age 10 he started sailing a Sailfish on the lake at his family’s summer home outside of his native Chicago. During high school he raced a Rhodes 19, and while he attended Marquette University he crewed on a variety of keelboats. He has raced to Mackinac 50 times-35 from Chicago and 15 from Port Huron. He has done countless weeknight and weekend races on the Great Lakes, has hauled his boats to Key West Race Week 15 times, competed in a dozen SORCs, and raced in four world championships. All nine of his boats have been called Nitemare. The name, Neill explains, dates back to his ex-wife Mary Ann, who didn’t like sailing. On trips she would take Dramamine and disappear to the berths below to sleep. Her ritual got to be a running joke, and instead of saying, “Good night, Mary Ann,” she would fall asleep so fast they would say, “Nite Mare.”
First in the Nitemare pedigree was a Morgan 33 in the late ’70s, followed by a few custom designs, a Corel 45, a Farr 40, and his current boats, a Great Lakes 70 and a Melges 32. His personal favorite is the Corel 45, which he campaigned in the ’90s. It was his first pure, grand-prix racing platform, as well as his baptism into professional-level sailing. He was a member of the crew, and rarely steered, but for three years he surrounded himself with top-shelf talent, including Robbie Doyle, Peter Isler, and Jud Smith. During this period he learned more from the pros, he admits, than he had in 25 years of sailing.
“One of the many things that makes sailing with Tom so special is his passion and love for the sport,” says sailmaker Pat Considine. “He really enjoyed the times when he was the worst sailor on the boat. He wanted to learn and improve and did so by surrounding himself with good people.”
Such tutorial prepared him well for his subsequent foray into Farr 40 class. This time, however, he had to drive. In the first few years he and his amateur crew were regulars in the middle of the pack. Every so often, he says, they had flashes of brilliance and “looked pretty good every now and then.”
As the class evolved to a much higher level, however, Neill felt the playing field was skewing toward big-budget teams. He became vocal about the creation of a Corinthian division within the class and subsequently won it three years straight in Key West. For Neill, it was the ideal arrangement. “You’ve got to work a little harder to stay on their [the front runners’] heels. So subconsciously you’re fighting for every boatlength that you can get just like they are. When you’re leading them around the weather mark you get your satisfactions. This is the best racing, mano y mano, because it makes you better.”
Neill’s eventual exit from the Farr 40 class (“We were getting too old”), and his eventual switch to the Melges 32, coincided with a life-altering discovery in 2006. He was diagnosed with lung cancer, and the news, understandably, hit him hard. Those close to him say, collectively, it hit his vast extended family even harder. The physical effects of his chemotherapy treatments have stripped him of his once strong and confident appearance, but his live-fast attitude remains characteristically Tom.
“The illness has magnified the importance of the sport in my life, and how I have benefited from it as a human being,” he says. “It has helped me in my business career. It has helped me in my personal life. I’m the lucky one. It’s obviously created a huge group of friends; that’s the most important part.”
“Win or lose we always have a good time,” says Tim Corkell, another regular crew. “After a tough loss, it may take some time for levity to return. The Nitemare team is not only a good crew, but good friends, too.”
Along the way Team Nitemare has certainly won and punted its share of races, and Neill has his favorites. One that still gets him fired up is the Port Huron Mackinac and Millennium 600 from Port Huron, Mich., all the way to Chicago, without a stop at Mackinac’s Pink Pony. It was the first time the crew raced on the 70-foot sled, and in 30 to 40 knots of wind they sailed 200 miles in less than 11 hours. It was, as he says, “the ride of a lifetime.”
But his most memorable win, was when Nitemare won the overall SORC trophy in 1997. “Ted Turner and Dennis Conner have their names engraved on that trophy,” he says. “We are pretty proud of that one.”
While he’s got his fair share of Mac race hardware and memories in the closet, it’s the buoy racing that has long been the love affair. “That’s where all the testament of your abilities and your skill shows up,” he says. “Any of us that have done any long-distance sailing knows full well that the element of luck enters into it at a much greater rate than it does on a course race or buoy race. Look at a Mac race or whatever the case may be and the boats just end up going left, right, and middle, and it becomes gripping. To me they are so different, they’re almost hard to even compare.”
The essence of his being is to have fun and win, but losing doesn’t haunt him. He simply keeps at it. His campaigns mean more than sailing on a boat. It is all about the Nitemare kin. “He’s truly one of the great ones,” says Stu Argo, who has raced against him many times. “You can tell the great owners from the others because his crew really enjoys being around him. Not because he had such a successful summer racing his Sled and Melges 32, and not because he sprinkles the infield with zest, but because he treats his crew like family and truly believes in his team as such. It’s not about the glory; it’s about the fun and time spent with close friends. So many people lose touch with that. He’s a tremendous competitor, too.”
After college Neill did what any smart post-grad might do: he joined the successful family business, Neill Cartage, a trucking and warehouse company started by his father in 1946. As its current president, along with his brother Rory, he has grown the business into a multi-million dollar operation. His reputation is as a hardworking and shrewd businessman. It wasn’t below him to re-use a strip of calculator paper, turning it over to use the blank side. And his efficiency carries over to the running of his boats-almost obsessively so. “He’d send you to the grocery story with a list,” says Kristine Hitz, a Chicago-area sailor and close friend, “and you’d better not come back with more than what was on it. He’ll have it figured out-right down to the slice-how much bologna he’d need for the week.”
Frugal, indeed, but it’s no secret that Neill has always been generous with both his money and his time. The Chicago Yachting Association recently named him Yachtsman of the Year for his commitment to the boating community. He’s been a champion of the Leukemia Cup Regatta Series, raising or donating more than $100,000 to the Leukemia and Lymphoma Society. He’s a top-level donor to the U.S. Olympic Sailing Team, and was a major supporter of Dawn Riley’s America True America’s Cup syndicate. But his greatest benefactors are Chicago’s junior sailors.
“I learned from my Dad at a young age the importance of giving,” he says. “Sailing has been a huge part of my life that I make a conscious effort to help at high levels and to assist disabled and youth sailing. If we don’t take care of the kids there will be no one to work the front end of the boat.”
Despite such local philanthropy, and his service to the club and its various committees, his reputation for revelry precedes him; he’s earned plenty of ire from CYC’s staff. His condo is just down the street, affording him not only a view of the club, but a short walk to his proverbial home away from home. He’s more than a regular: his opinions, informed and brutally honest, are sought after by those involved with the club’s racing activities. Allan McMillan, who once chaired the club’s offshore committee, says when he first arrived, it was abundantly clear whom he had to seek out first, and often. “His honest opinions are based on his understanding of the history of the club and the people. He does not vacillate, and his opinions always have the interest of good competition, it never had to do with what he wanted or with what would benefit him. In terms of the hierarchy of respect, he’s right there at the top because he knows racing at Chicago Yacht Club.”
Neill is, however, far from the “model” member, and admits to the irony of his receiving the Yachting Award. He has several letters of reprimand in his file, and his membership has twice been suspended: once for mistaking the parking lot for the men’s room, and on another occasion, after a spirited party on the chartered former presidential yacht, El Presidente, Neill and his revelers returned to the club, but were refused service at the bar. The rejection did not go well and words were exchanged.
There are countless Nitemare stories that make the rounds of the Chicago waterfront. For example, there’s Neill’s late night ride across a hotel swimming pool in a small boat that served as a salad bar. Another story, told by crew Tone Martin, has Nitemare dropping out of a light-air race off Milwaukee. Once back at the dock, Neill fell asleep while the crew visited the local pub. When they returned at 3 a.m., he got up and told stories until the sun came up.
The shenanigans even carry over into the off-season, with ski trips, crew parties, and random flights of fancy. “There’s this burger joint about an hour out of town that he just loves,” says Hitz. “And every year he would rent a limo, pack it full of couples, and drive up to this place. He’d be the one sitting on the floor and making sure everyone was a having good time: he’s the only one I know that would rent a six-hundred dollar limo to go get a six-dollar burger.”
His cancer has curbed some of his extra curricular activities, but has done little to dampen his positive outlook, and certainly not his sense of humor. Two years ago, Neill (who has three children: Bill, 32, an electrical engineer in Chicago, Tom, 31, a grad student at Johns Hopkins, and Sarah, 29, an attorney also living in Chicago) married his long-time companion Amy Duitsman. Periodically, they send updates on his health, and in spite of the gravity of his situation, the messages are filled with self-deprecating humor: “Things are stable, except for the fluid in my right lung. There is so much there I could fish. I don’t need to go to the Jersey Shore to listen to the surf, all I do is sway side to side and I sound like a tsunami hitting the beach.”
Neill says he continues to turn to humor to make the crew feel more comfortable with the illness. “Tom is going out and living his remaining time, being it sailing, skiing, or just being with his buddies,” says crew John Stanley. “He’s not crying about this. Trips are planned, races are won or lost, either way, and the entire fleet cheers when he shows up.”
Over the past year and a half Neill has endured chemo and radiation treatments with many debilitating side effects, yet he continues to foster the vast sailing family that, in turn, fosters him. He plans to take his team to Key West Race Week and the Miami Grand Prix, as well as entering the 100th running of the Mackinac Race next summer. And whether he is on the boat or not doesn’t matter. He has chartered a hard bottom inflatable so he can watch, coach the guys, and maybe even take a turn on the tiller.
“This is what he’s all about,” says Hitz. “If the party is about to end, and everyone is dancing and having a good time, Tom has always been the one who will slip the band enough money to play an extra hour or somehow convince the bar tender to leave an ice bucket full of beer and the keys to lock up on the way out.”
It’s as if he’s known all along that life really is too short to not make the most of it.