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Catching Up with Dawn Riley, Part 2

Readers — This is a follow-up to Mark Reid’s interview with Dawn Riley that appears in Sightings in the August issue of Latitude 38.

Maiden in the Whitbread

We turned the clock back a bit, and Dawn Riley recounted a few memories from Maiden, Mighty Mary and America True.

On Maiden (1989-90 Whitbread Around the World Race, with an all-female crew, famously referred to by legendary sailing writer Bob Fisher as a “tin full of tarts”), Riley said she was like her current trainees at Oakcliff Sailing Academy. “Everything was, like: ‘Wow, frostbite! Oh my God, we broached! We almost hit a whale! This is so fricking cool!’ The only time I was really scared was when we were leaving the dock for the start. I’m thinking, ‘Oh-oh — what am I doing?'”

About the documentary, Maiden, Riley said, “The footage is almost exclusively from the race, which came from our boat. The story of the race is really good. The only Hollywood-esque part is they made it look like Tracy Edwards went from a poor child to the world’s best yacht racer, and there were 11 of us on board. But that’s the story; it made it a much better story.”

Maiden cast (crew)
The female crew from the Around the World Race reunited for the premiere of the documentary Maiden. Skipper Tracy Edwards is fourth from right and Dawn Riley is in pink in the center.
© 2021 New Black Films / Sony Pictures

Maiden, the yacht, visited the Bay Area as part of a world tour promoting the release of the documentary in 2019.

Mighty Mary and the America’s Cup

“On Mighty Mary [in the 1995 America’s Cup Defense trials in San Diego], the low was when we beat Dennis Conner and eliminated him, and then found out that management — which was all male by the way — had decided that that was only a points race, not an elimination race,” recounted Riley. “That was, by far, the worst.

“That is when I said that I will never ever again be part of a team where there is not diversity,” said Riley. “At least gender diversity and hopefully racial diversity in leadership. As all business, all teams should be.”

Mighty Mary crew
The Mighty Mary crew from 1995. Dawn is fifth from right, first row with mainsheet line in hand.
© 2021 Gilles Martin-Raget

As far as having Brad Dellenbaugh (the ‘bearded lady’) brought in on an otherwise all-female crew, Riley recalled, “That was fine. I was the only one on the team who had raced on an IACC boat before that, so in some ways it was a semi-artificial team to put together a bunch of women. We didn’t lack strength, and we didn’t lack a lot of stuff. What we were missing was the depth of experience in the tactician role.”

America True and the America’s Cup

The high point of Riley’s America’s Cup career was her involvement with the San Francisco Yacht Club-flagged America True team in the 1999-2000 Louis Vuitton Cup Series in Auckland, New Zealand. Riley was the CEO and co-skipper of the syndicate. The team started with an impressive 21-9 record before falling short in the semifinals.

America True vs. Nippon
America True led by Dawn Riley fends off Nippon in the 2000 Louis Vuitton Cup in Auckland. True ran a strong series back then, but their foundation’s support for youth programs runs just as strong today.
© 2021 Gilles Martin-Raget

The foundation, led by Riley, promotes and introduces young people to the joys of sailing nationwide. The America True Youth Program was born in 1997. America True was the first America’s Cup syndicate in history to be headed by a woman, and the first to have a coed crew.

“We believe that sailing can teach youth valuable life lessons including confidence, independence, strategic thinking, teamwork and respect for the environment,” states Riley. “We believe that sailing can, and should, be open to all, regardless of gender, culture, ethnic or economic background.”

Their motto of “If you can dream it, you can do it” certainly carried Riley and her team of Maxi Acorn students through the last few weeks with experiences and lessons that will last a lifetime.

Oakcliff Sailing and the Bayview-Mackinac Race Record

Dawn Riley has had a very busy few weeks. She and her Oakcliff Sailing Academy students have been sailing on OC 86 (ex-Windquest) in two races to Mackinac Island, from Chicago and from Port Huron, Michigan.

In the second race, hosted by Detroit’s Bayview YC, OC 86 blistered the record by more than two hours, finishing in 17 hours, 11 minutes, 18 seconds. That easily beat the record of 19 hours set by the Volvo 70 II Mostro in 2013.

“They smoked the record!” said Greg Thomas, Bayview YC race chair. “The Shore Course has been our main course for over 80 years. They didn’t just beat the record, they beat the heck out of it. That boat is very fast.”

“In the backs of our minds we knew the weather forecast could be magic for this boat, and it didn’t disappoint,” said Riley. “It was like some higher power was paving the way to for us to break the record.”

OC 86 crew at the dock
OC 86’s crew celebrate hard-fought line honors. They shattered the race record in the 97th edition of the Port Huron to Mackinac Race.
© 2021 Martin Chumiecki / Photo Element

“We had four professional crew onboard,” said Riley. “We had David Blanchfield, who is Katie Pettibone’s [Mighty Mary] husband from Port Huron; Jim Turner, who was on mainsail for me on our 2007 ACC boat Areva; and Brad Farrand, a young Kiwi with Volvo experience who started his match-racing career at Oakcliff.” Navigator Suzy Leech took advantage of a patchwork of three massive high-pressure systems as they dodged tornadoes racing up the Michigan shoreline on a wet and windy Lake Huron.

“Everybody is very aware that we ran aground at the start [on July 24]. We did so spectacularly because every single [blankety-blank photographer] took pictures of it. But we got off, we rebooted, and we talked through it as a learning lesson. At least five of us could have mentioned that red-right-returning is the other way in the Lakes, so a whole bunch of us ‘salted’ sailors now understand unsalted waters. We restarted, and from the weather routing early on, everyone kept saying, ‘This could be a record run.’ I said, ‘Zip it! Do not talk about it!’

“Especially after running aground, we said we are going to be smart first and worry about being strong and fast second,” stated Riley. “When Natalie J’s mast came down, I was on the main, in the process of taking our spinnaker down to go bareheaded. We could see the weather coming, and we were trying to be smart. We were going for less wind, and we had already pulled up to the tornado side of the front, which we could see, and then there was the darker leeward side, so we thought we could thread the needle. Then we saw the water coming in as a white squall; it topped out at 34 knots.

“At that point the kids were just hanging on for the ride, thinking, ‘Someone else must know what’s going on!’ But now, all those students have that experience. They understand now how buoys work on in the Great Lakes, the way a thunderstorm works, what a tornado looks like, and what 40 knots looks like! And how not to worry about making a perfect sail change — just get the fricking sails down and restart.

“One of the kids goes, ‘Is this like the Southern Ocean?’ Yeah, ha ha! Except here (on Lake Huron) it is 78 degrees and the waves are an eighth of the size!”

Wings costume
Wings over Mackinac! There is no doubt that the Bayview awards party is a lot more fun than their ‘kin’ from Chicago as Endless Summer entertain all in a very family-friendly way. Though the Porch Party still has its charm.
© 2021 Martin Chumiecki / Photo Element

The goal for OC 86 going forward is Atlantic distance races like the Newport to Bermuda Race next year.

“I keep thinking that at Oakcliff there is no way I could be busier, then we add another project!” said Riley. “We partnered with American Magic, and also the Ocean Race team 11th Hour Racing.”

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