Annual Rolex Awards: Measuring Each Moment

These top sailors have thrilling relationships with time.

Rolex Yachtsman of the Year
Rolex Yachtsman of the Year Steve Benjamin at the helm with his crew.Courtesy Rolex

A little before Annie Haeger was born, Steve Benjamin was on the cover of Yachting. He was with his crew on a 505, pushing the limits of speed. “We were hellbent, go-all-out,” Benjamin recalls, sounding a lot like Haeger talks today. She is training to represent the United States at this year’s Olympic Games in Brazil — playing through the pain of a recent back injury. “Pretty much the hardest thing for me,” she says, “is to take a break.”

Benjamin and Haeger have met, but they don't usually race each other on the water. Their names, however, will be forever intertwined as the 2015 Rolex Yachtsman and Yachtswoman of the Year.

Rolex Yachtswoman of the Year
Rolex Yachtswoman of the Year Annie Haeger at the helm with her crew.Courtesy Rolex

The awards come at very different phases in their lives. Benjamin, who is 60, has enjoyed a long and varied career as a helmsman and tactician aboard yachts of all kinds, being dubbed “Master of Faster” in one of the many articles written about his epic races. Haeger, who is 25 and always at the helm, describes herself as more of a NASCAR sailor, competing in short-court buoy races that rarely last more than an hour.

For both, though, earning a Rolex award seems fitting because their relationship with time is so similarly intimate. Whether they are talking about a race that lasts 36 minutes or 36 hours, they are constantly trying to shave seconds.

Rolex Yachtsman & Yachtswoman of the Yea
2015 Winners: Annie Haeger and Steve Benjamin were honored at the New York Yacht Club in March.Courtesy Rolex

“It’s fractions of seconds,” Haeger says. “There are clumps of boats crossing the finish line. If you can get that fraction of a second anywhere around the racecourse, that’s a five-boat gain, right there.”

Just last year, Benjamin says, time was a bitter mistress for his crew during the Fort Lauderdale to Key West Race.

“We matched up against Rambler for the first time,” he says. “That’s a brand-new 90-footer owned by [noted yachtsman] George David. They were several hours ahead of us, but we knew, on corrected time, we were very close. Our navigator knew we had a chance to beat them, but he kept prodding us. First it was, ‘We’re 20 minutes behind.’ Then he’d say, ‘10 minutes behind.’ He was pushing us because he knew it was virtually a tied score.

“When we went to look at the posted score, we’d won by seven seconds. And that’s on about a 20-hour race.”

Rolex Yacht-Master
The Rolex Yacht-Master comes in various styles, including Everose Gold (left) and Yellow Rolesor.Courtesy Rolex

Haeger had a similar close call while racing in Europe last year.

“We were battling it out with the Polish girls at the finish,” she says. “Usually for us, an O flag goes up when there’s 8 knots or more of breeze. That means you’re allowed to pump, ooch or rock your boat as much as you want, all around the racecourse. It gets very physical. It’s so you can release the boat and get it to plane easier. That’s full-out for the crew downwind. They’re pumping the spinnaker and out of breath. I remember thinking it was a tie because it was so close. We beat them by less than a second.”

"When we went to look at the posted score, we'd won by seven seconds. And that's on about a 20-hour race."

- — Steve Benjamin, 2015 Rolex Yachtsman Of The Year

Even when they’re not on the water, both winners say time is on their minds. Haeger feels the increasingly loud beat of the Olympic trials clock in her future, while Benjamin — who says he has role models in their 80s — is learning to enjoy a new relationship with time as he ages.

“I had prostate cancer six years ago,” he says. “That did change my attitude about time. It made me realize that every day is important. Every day that we go on the water, it’s great to be able to do that.”

1961-2014 winners

2014 Terry Hutchinson/Stephanie Roble 2013 Brian Porter/Jody Starck 2012 Johnny Heineken/Jen French 2011 Bill Hardesty/Anna Tunnicliffe 2010 Stan Honey/Anna Tunnicliffe 2009 Bora Gulari/Anna Tunnicliffe 2008 Terry Hutchinson/Anna Tunnicliffe 2007 Jeff Linton/Sally Barkow 2006 Jud Smith/Paige Railey 2005 Nick Scandone/Sally Barkow 2004 Paul Foerster and Kevin Burnham/Jody Swanson 2003 Augie Diaz/Hannah Swett 2002 John Kostecki/Liz Baylis 2001 Steve Fossett/Cory Sertl 2000 Mark Reynolds and Magnus Liljedahl/JJ Isler and Pease Glaser 1999 Eric Doyle/Dawn Riley 1998 Paul Cayard /Betsy (Gelenitis) Alison 1997 Chris Larson/JJ Isler 1996 Dave Ullman/Courtenay (Becker) Dey 1995 Ed Baird/Cory Sertl 1994 Ken Read/Danielle Brennan 1993 Cam Lewis/Betsy (Gelenitis) Alison 1992 Kevin Mahaney/Julia Trotman 1991 Ed Adams/JJ Isler 1990 Jim Brady/Courtenay Becker 1989 Larry Klein/Jody Swanson 1988 John Kostecki/Allison Jolly and Lynne Jewell 1987 Ed Adams/Susan Dierdorff Taylor 1986 Dennis Conner/JJ Isler 1985 Ken Read/Kathy Steele and Heidi Backus 1984 Bill Buchan/Betsy Gelenitis 1983 Dave Curtis/Wendy Thomson 1982 Randy Smyth/Betsy Gelenitis 1981 Dave Curtis/Betsy Gelenitis 1980 Dennis Conner/Lynne Jewell 1979 Ted Turner/Nell Taylor 1978 Buddy Melges/Bonnie Shore 1977 Ted Turner/Jan O'Malley 1976 Lowell North/Allison Jolly 1975 Dennis Conner/Joan Ellis 1974 Ted Hood/Sally Lindsay 1973 Ted Turner/Sally Lindsay 1972 Buddy Melges/Jane Pegel 1971 Ding Schoonmaker/Jane Pegel 1970 Ted Turner/Jan O'Malley 1969 Robert F. Johnson/Jan O'Malley 1968 Lowell North/June Methot 1967 Bus Mosbacher/Betty Foulk 1966 Bill Cox/Jerie Clark 1965 Dick Tillman/Timothea (Schneider) Larr 1964 Bob Bavier/Jane Pegel 1963 Joe Duplin/Leggie Mertz 1962 Bus Mosbacher/Sue Sinclair 1961 Buddy Melges/Timothea Schneider