Please select your home edition
Edition
Pantaenius Sail 2025 AUS Leaderboard

Rolex Big Boat Series - 50 years of big boat racing- a retrospective

by Barby MacGowan on 13 Sep 2014
The 55’ S&S yawl Orion in the 1964 St. Francis Perpetual Trophy Series St. Francis Yacht Club Archives
2014 Rolex Big Boat Series - There is one person who can tell the full story of the Rolex Big Boat Series, in amazing detail, starting from its humble beginnings. It is the man whose idea it was to start it back in the 1960s: St. Francis Yacht Club’s Staff Commodore (1975) Robert C. Keefe, who at the age of 84 has been a member for 65 years and remembers the early days of the then-called St. Francis Perpetual Trophy Series as if it were yesterday.

As a Traveling Sales Manager for (and eventually President of) Barient Winches, Keefe spent plenty of time in Southern California, getting to know the area’s principal yachtsmen. Recognizing that the respective collections of fine yachts there and in northern California should get together, he suggested establishing a race. It was 1963, and there would be time to organize it for 1964.

'The Commodore said it wasn’t the worst idea in the world, but we needed an organizer, someone to ramrod this,' said Keefe, who was the natural choice for filling the role. 'The southern California sailors said ‘we’d really like to do it, but we have to stay on our home waters for the events on our sailing calendar. When it tapers off later in the year, we’ll come to San Francisco.’ That’s how September came about.'

That first year, the yacht club invited 25 boats to sail in its series, the vast majority of them over 60 feet long. 'They were mostly from Southern California but we asked some from New York, Florida, Boston…not so much because we thought they’d drop in, but we wanted to play with the big boys. We ended up with four from here and four from Southern California.'



The inaugural regatta was raced on a Monday, Wednesday, Friday and Saturday, so the out-of-town sailors could go back and forth to their offices. 'That worked well, and in ’65 a few more boats came from San Diego, some from Seattle…even Storm Vogel arrived from Holland, sailing through the Golden Gate. In ’67, the regatta ran a little out of gas only because California boats began going to the Eastern Seaboard to race, but we still had a big fleet of 50 footers (about 20), so we created a second trophy for them. Then in 1970, big boats matriculated back to the West Coast.' (Today, specially engraved Rolex timepieces are traditionally awarded to winners of the St. Francis Perpetual Trophy; the City of San Francisco Trophy; the Richard Rheem Trophy; the Keefe-Kilborn Memorial Trophy; the Atlantic Trophy; and the Commodore’s Cup.)

Keefe continued 'ramrodding' the event for ten years, and it was his and his fellow club members’ fine salesmanship that convinced some of the greatest boats of all time to compete. They included the 67’ yawl Chabasco from Newport Beach and John B. (Jim) Kilroy’s various Los Angeles-based Kialoas (Kialoa II competed in the inaugural event, finishing second to Jim Wilhite’s 63-foot Sparkman and Stephens yawl Athene, which won the original St. Francis Perpetual Trophy.)



'Jim was the guy who would say ‘this has got to be the best place in the world for this kind of sailing,’' said Keefe. 'This is no hurricane gulch, but certainly we have 15, 18, 20 knots every day. Then if you want light air, you can go over to Marin County and on the same day have 10-12 knots of breeze. The range of wind the gods gave us here in San Francisco did wonderful things for us. We had this wonderful asset.'

Keefe recalls the very first race of the first series, which started at noon and went out under the Golden Gate Bridge into the ocean. 'We didn’t get back until midnight. God love it out there, but besides being cold, wet and miserable, that’s not what the sailors had come for. They wanted to have good, fair racing in our little puddle right out there, between the bridges and on the waterfront here,' said Keefe, pointing to the water that famously laps at the club’s northern facing side and presents the Golden Gate Bridge and Alcatraz Island in one sweeping glance.

Keefe also remembers the endearing moments that are typical of those that keep many participants coming back year after year, if not decade after decade. 'Roy Disney had many occasions to have his boats here (Shamrock and various Pyewackets). The first year Rolex was a presenting sponsor, it was opening night and there was a watch display out front. When I went by, what was sitting on top of the glass case but a Mickey Mouse watch, with a nice little stand and a big dial. That really kind of broke everyone up. I thought it was hilarious, but Roy never admitted to it; maybe his crew cooked it up.'

'We have a lot of fun,' said Keefe. 'That’s one reason these guys come back. It’s an enjoyable experience - the racing, the club and San Francisco itself.'

Today’s Top Tallies

The boats aren’t all as big as they used to be at the Big Boat Series, but Kame Richards (Alameda, Calif.), today’s Boat of the Day winner, had a theory about this: 'I think that historically we used to have one really special thing that we did for fun and that was sailing. We no longer have one thing; we have five things that we do for fun in addition to sailing. Sailing hasn’t changed; personalities have changed.'

For him, and the 101 sailors competing here, what matters most (after the fun) is the hard-core competition. Richards, sailing his Express 37 Golden Moon, claimed two victories today, adding them to his perfect score line from yesterday.



'It’s not as easy as it looks,' said Richards, who has been racing at this event for upwards of 35 years and racing in the Express 27 Class for 12 years. 'We’ve never done this well before; we’ve won before, but right now we have four points and the next closest boat has ten, which is nice, but uncommon.'

'What I enjoy about sailing is how hard it is. It is exactly like running a business. You have so many resources, and as a manager, you have to marshal your assets. We’ve been working on this for a long time.'



In the J/120 Class, Barry Lewis’s Chance also has a reputation for making it on to the podium, and this year the team has protected its first place position that it initiated yesterday. 'Each day the margin of error gets smaller and smaller at this event, and each boat steps up their game a little more,' said Lewis, adding that there is a strong fleet of competitive boats that race each year, including David Halliwill’s Peregrine which is currently biting at his heels, only one point behind in second.

'This year we have some new boats racing, including the Japanese team onboard Julian, which is super-fast and very competitive. In this fleet, if you make a mistake it will cost you big. Our game plan moving forward is to minimize mistakes, sail fast upwind and get great starts.'

Also holding on to class leads established yesterday are Bruce Stone’s J/105 Arbitrage, Dorian McKelvy’s J/111 Madmen and Don Jesberg’s Melges 24 Viva.

For full details on the 2014 Rolex Big Boat Series, please visit website.

2014 Rolex Big Boat Series - Top-three results

Place, Yacht Name, Type, Owner/Skipper, Hometown, Results, Total Points

HPR (HPR - Seven Boats)

1. Tai Kuai, RP 44 44, Daniel Thielman, Tiburon, CA, USA - 2, 4, 1, 4, 11
2. Whiplash, MC 38 38, Donald Payan, Hillsborough, CA, USA - 4, 2, 3, 2, 11
3. Rock and Roll, Farr 400 40, Bernard Girod, Santa Barbara, CA, USA - 1, 3, 5, 3, 12

J 70 (One Design - 13 Boats)

1. Double Trouble, J 70 22.75, Andy Costello, Point Richmond, CA, USA - 8, 1, 2, 1, 12
2. Bottle Rocket, J 70 22.75, David Schumann, Mill Valley, CA, USA - 3, 2, 4, 4, 13
3. Perfect Wife, J 70 22.75, Chris Andersen, Pt. Richmond, CA, USA - 5, 3, 6, 2, 16

J 105 (One Design - 19 Boats)

1. Arbitrage, J 105 34.5, Bruce Stone, San Francisco, CA, USA - 1, 3, 2, 1, 7
2. Godot, J 105 34.5, Phillip Laby, San Francisco, CA, USA - 2, 2, 1, 8, 13
3. Blackhawk, J 105 34.5, Scooter Simmons, Tiburon, CA, USA - 5, 1, 3, 5, 14

J 111 (One Design - Seven Boats)

1. Madmen, J 111 36.5, Dorian McKelvy, Portola Valley, CA, USA - 2, 1, 3, 1, 7
2. Big BLAST!, J 111 36.5, Roland Vandermeer, Hillsborough, CA, USA - 5, 2, 1, 3, 11
3. Bad Dog, J 111 36.5, Dick Swanson, Los Altos Hills, CA, USA - 1, 6, 4, 2, 13

J 120 (One Design - Seven Boats)

1. Chance, J 120 40, Barry Lewis, Atherton, CA, USA - 2, 2, 3, 2, 9
2. Peregrine, J 120 40, David Halliwill, New York, NY, USA - 4, 1, 4, 1, 10
3. Mister Magoo, J 120 40, Stephen Madeira, Menlo Park, CA, USA - 5, 3, 2, 4, 14

Melges 24 (One Design - Nine Boats)

1. Viva, Melges 24 24, Don Jesberg, Belvedere, CA, USA - 1, 1, 1, 1, 4
2. Insolent Minx, Melges 24 24, Zhenya Kirueshkin-Stepanoff, Mount Hamilton, CA, USA - 2, 2, 2, 2, 8
3. Bones, Melges 24 24, Robert Harf, Sonoma, CA, USA - 3, 3, 7, 4, 17

Farr 40 (One Design - 15 Boats)

1. Plenty, Farr 40 40, Alex Roepers, New York, NY, USA - 2, 1, 3, 1, 7
2. Groovederci, Farr 40 40, John Demourkas, Santa Barbara, CA, USA - 5, 4, 2, 2, 13
3. Nightshift, Farr 40 40, Kevin McNeil, Annapolis, MD, USA - 3, 5, 7, 5, 20

Express 37 (One Design - Seven Boats)

1. Golden Moon, Express 37 37, Kame Richards, Alameda, CA, USA - 1, 1, 1, 1, 4
2. Expeditious, Express 37 37, Bartz Schneider, Crystal Bay, NV, USA - 3, 2, 3, 2, 10
3. Elan, Express 37 37, Jack Peurach, San Francisco, CA, USA - 7, 4, 2, 3, 16

SF Bay ORR (ToT - 10 Boats)

1. Encore, Sydney 36 CR 36, Wayne Koide, San Anselmo, CA, USA - 1, 1, 2, 4
2. BustinLoose, Sydney 38 38'6, Jeff Pulford, Salinas, CA, USA - 2, 3, 3, 8
3. Tupelo Honey, Elan 40 40, Gerard Sheridan, San Francisco, CA, USA - 4, 4, 1, 9

Multihull (BAMA) (ToT - Five Boats)

1. Orion, MOD70 70, Tom Siebel, Redwood City, CA, USA - 4, 1, 1, 1, 7
2. SmartRecruiters, Extreme 40 40, Jerome Ternynck, San Francisco, CA, USA - 1, 3, 2, 3, 9
3. Shadow, ProSail 40 Cat 40, Peter Stoneberg, Tiburon, CA, USA - 3, 2, 3, 2, 10

Boat Books Australia FOOTERNorth Sails Loft 57 PodcastRooster 2025

Related Articles

America's Cup: Kiwis advertising for key people
Emirates Team NZ seeking new people for key roles ahead of its 12the America's Cup campaign Emirates Team New Zealand, the current America's Cup champion is gearing up for the 2027 Defence of the most prestigious trophy in sailing. The team has advertised eight positions in the IT, Meteorology and Engineering areas
Posted today at 9:54 am
Russell Coutts explains SailGP's investor value
Russell Coutts explains the growth of SailGP and why investors are chasing a slice of the action. SailGP co-founder and CEO Russell Coutts was interviewed last week, ahead of the weekend's Mubadala New York Sail Grand Prix, where he discussed the hard to understand investment, and growth of SailGP.
Posted today at 3:27 am
Admiral's Cup vs. Rolex Fastnet Interclub Trophy
CYCA is proud to be competing in two prestigious interclub competitions The Cruising Yacht Club of Australia (CYCA) is proud to be competing in two prestigious interclub competitions — the revived Admiral's Cup and the Martin Illingworth Trophy — as part of the 2025 Rolex Fastnet Race.
Posted today at 2:12 am
5.5 Metre World Championship Day 3
Aspire is new leader in Sopot Aspire (POL 17, Przemyslaw Gacek, Mateusz Kusznierewicz, Kilian Weise) has taken a 10-point lead at the 2025 5.5 Metre World Championship in Sopot, Poland, after two more races on Wednesday in a cold northerly between 12-23 knots.
Posted on 11 Jun
WingFoil Racing World Cup Switzerland day 2
Rising stars and tight battles on Lake Silvaplana Day two of the Wingfoil Racing World Cup Series in Silvaplana delivered another spectacular day of competition, despite a short initial delay as racers waited for the wind to fill in.
Posted on 11 Jun
Introducing EDGE - Your All-Around Advantage
North Sails 3Di Endurance Edge - from Regatta Starts to Sunset Sails North Sails 3Di Endurance Edge - from Regatta Starts to Sunset Sails. EDGE is as ready for regattas as it is for day sailing. Lighter and lower stretch than paneled or string sails. Integrated ENDURANCE Surface™ delivers a durable and easy-to-handle sail.
Posted on 11 Jun
The Ocean Race Europe to contribute ocean data
All of the competing IMOCA race boats will carry specialised science equipment The Ocean Race Europe, an offshore sailing race that connects seven European cities from the Baltic to the Adriatic Seas will see all of the competing IMOCA race boats carrying specialised science equipment.
Posted on 11 Jun
Loro Piana Giraglia 2025 Offshore Race Start
A total of 97 yachts are now racing along the 241-nautical-mile course At exactly 11:55 this morning, the starting procedures kicked off on the line off Saint-Tropez, sending the fleet toward the Giraglia rock.
Posted on 11 Jun
Foiling Week 2025: A stellar edition set to launch
Five classes will compete: Moth, WASZP, Switch One Design, BirdyFish, and ETF26 Foiling Week returns to Europe for its 12th edition, taking place in the last week of June, after its first-ever event in Pensacola, Florida, earlier this March.
Posted on 11 Jun
Women sailors reflect on Admiral's Cup inclusion
Pivotal milestones, but there is still so much more to achieve The Royal Ocean Racing Club (RORC) has long acknowledged the slow but steady path toward gender inclusion in offshore sailing.
Posted on 11 Jun