When senior Hailey Thompson looks out onto the water, she takes a deep breath, clearing her mind before the horn blows, signaling the start of the race. A wave of adrenaline rushes through her as she looks around at her competitors, some twice her age. Putting this fact out of her mind, she remembers the months of prior training, the years of competing and the endless practices with her teammates that have prepared her for this day: the U.S. Women’s Sailing Match Racing Championship.
Convinced to start sailing by watching her older brothers take to the sport, Thompson’s career jumpstarted from a young age.
“[My brothers and I] started out at a summer camp at the San Francisco Yacht Club when I was seven years old … I sailed there for two or three summers and, by that third summer, I was moving onto the beginning race teams,” Thompson said.
When she first started sailing, Thompson was not exactly drawn to the sport. She sailed Optis, which are notoriously small sailboats, and only began to truly enjoy racing once she found her footing.
“[The coaches of the club team] would take us out and practice in the bay … it just felt windy and scary. The boats are slow and you’re always cold and wet and I thought, ‘this is miserable and I hate sailing,’” Thompson said.
While Thompson decided to stick with sailing, she began to discover that she enjoyed racing different types of boats in various event types.
“Four hundred and twenty boats were my segway and then I started to sail lasers, which are single-handed boats that I’ve had a lot of success with, … [the change in race style] really marked a turning point for me,” Thompson said.
As Thompson began to progress in her newfound love of sailing, she started racing for Redwood’s varsity sailing team and instantly became a leader and talented competitor. Past teammate and 2022 Redwood graduate Katie Norris described Thompson’s role on the high school team.
“She’s always been really good at rallying people even from a younger age, she’s so respectable in the community and she’s just always been a natural leader,” said Norris.
Thompsons’ willingness to put herself in unknown situations and take risks even in a high-stress environment is what stood out to Nicole Breault, a four-time winner of the National Women’s Match Racing Championship.
“I was introduced to Hailey by her high school coach Shawn,” Breault said. “We were talking about how to bring in some young blood to the game and focus our efforts locally. It turned out that Hailey was available to sail with me in a race in March. We hit it off and had a great time, finishing second in that event.”
These opportunities have allowed Thompson to show her strengths on the water while also building connections with team members.
“I [sail whenever] I can. If someone asks ‘does anyone want to drive this boat?’ I say ‘yeah!’ If somebody says ‘hey, does anyone want to crew on this boat?’ I say ‘sure!’” Thompson said.
Thompson emphasized the importance of building relationships within the sailing world and expressed that one of her most inspirational connections is that with Breault.
“[Breault] is nationally one of the top female match racers … and she’s just a badass. She is so into [coahing] and bringing up young sailors and young women which is not something that you see anywhere else — having lots of women in high-stakes or high-stress environments where typically there’s a lot of discrimination … It’s still a fairly new thing to have women in boats at really high levels,” Thompson said.
Breault’s inclusive, can-do mentality has made a real impact on Thompson, along with many other female sailors, both at the beginner and professional levels.
“​​There’s a real comradery that seems to always happen at the end of [racing] events … I think the key to taking [female inclusion] to the next step really is mentoring and coaching women to help them find what opportunities already exist in the game and [encourage them to have] the confidence to put themselves out there,” Breault said.
Additionally, Norris expressed her appreciation that Thompson was breaking the typical mold of the sailing world, representing the population of athletic, talented female racers.
“[Thompson is] so strong and she can really stand up for herself, which is good because sailing is definitely a male-dominated sport … I just have so much respect for her,” Norris said.
As Breault was preparing to compete in the U.S. Women’s Match Racing Championship in mid-August, she ran into an unfortunate snag in her plans, with a few members of her race team recovering from COVID-19 and unable to attend. Breault, however, already had someone in mind to fill the gaps in her team.
“My team had an automatic invitation because we had won the event last year in 2021 … So, when my technician couldn’t sail, I was thinking about who I might like to sail with … I wanted to give Hailey the opportunity to race at a championship level with some of the top women in the country,” Breault said.
Despite the fact that the championship took place during the first week of her senior year and she was fairly new to match racing, Thompson showed no hesitation in her decision.

“[Breault] flew me out to New York for four days and we sailed the championship together and it was phenomenal … We ended up winning bronze,” said Thompson.
So, while the rest of her class was kicking off the school year, receiving textbooks and having their syllabi signed, Thompson was pushing boundaries in the sailing world: competing in a national championship, driving herself to new limits and continuing to progress, trends she hopes to replicate in the future.
“At one point, when I’m good enough or have my own money and my own boat, I’ll start introducing other people into [sailing]. It’s one of those [sports] where you bring people up with you. So, I hope that will be me: meeting new people, sailing in new places and racing in cool events,” Thompson said.

To access a timeline of Hailey Thomson’s sailing career click below.