Caraline Oakley, A Pioneer In Girls Athletics At Southampton High School, Will Continue Golf Career In College

Caraline Oakley didn’t set out to be a trailblazer — it just sort of happened that way, the byproduct of an unwavering obsession with golf. It’s a love affair that’s been with her for more than half her life and has been a consistent motivating force, shaping her high school career and playing a role in her future.

The Southampton High School senior signed her letter of intent on January 7 to play on the women’s golf team at Washington University in St. Louis, Missouri. It’s one of the top Division III programs in the country and became Oakley’s top choice not only because of the golf team’s track record of success, but also because of the school’s stellar academic reputation, an imperative for Oakley, who plans on going pre-med and one day becoming a pediatrician. The fact that she’d be allowed to also play intramural basketball or volleyball was a draw as well.

Playing golf alongside girls is still a relatively new experience for Oakley, who first picked up a club at the age of 7. Most of her involvement in the game has been in a predominantly and, at times, exclusively male setting. Southampton High School did not have a girls golf team until Oakley’s sophomore year, and only created one because of the persistence of Oakley and a few other female players who lobbied the school to start one. Before that, she played three years on the boys varsity team, following in the footsteps of her older brother, Christian, who graduated in 2017. She also made history outside of her school setting, becoming the first female caddy in the 129-year history of the famed Shinnecock Hills Golf Club, taking a job there in the spring of 2017.

Oakley’s pure love of the game is the primary reason she pushed past any discomfort she may have initially felt in both of those situations. But her ability to thrive both at Shinnecock and on a majority boys team (former teammate Kaitlyn Browne, who is now at St. Anthony’s, also previously played on the Southampton boys varsity team), is also a function of her personality. Oakley is energetic, talkative and outgoing, and clearly driven to succeed, not only on the course, but in every aspect of life. She has a voracious and seemingly insatiable appetite for athletics and competition — she’s currently playing varsity basketball, has played tennis, softball and volleyball at various times in her years at Southampton, and also played on a travel club volleyball team — and has a seemingly innate desire to keep moving, in both the literal and metaphorical sense. She says she will often hit the gym after basketball practice, before heading home to finish her homework, and welcomed the challenge of balancing commitments to multiple sports in the same season, whether it was finding time to hone her golf game on weekends or balance varsity basketball practice and games with club volleyball practice and matches.

“I can’t be sitting at home doing nothing,” she said in an interview last week. “It’s purely a go-go lifestyle for me. I couldn’t get out of that routine.”

One of the earliest routines for Oakley was getting out on a golf course at a young age, with her golf-playing parents — mother Patty and father Michael — and her older brother, Christian. The family belongs to Southampton Golf Club, and Oakley said the influence of both parents and a talented older brother were a constant motivating force from early on.

“I really strived to be as great as him,” she said of her older brother, who was the top golfer for the Southampton varsity for several years and is now a junior at the University of Notre Dame.

An appetite for competition burgeoned along with a desire for improvement, and by the age of 10, Oakley was competing in nine-hole youth tournaments around the tri-state area. Two years later, she was up to 18-hole competition. Golf appeals to her, Oakley says, because of what it requires both physically and mentally, and how honing those skills translates to everyday life.

“I truly believe that the patience you need and the focus the game teaches you connects to outside life and my studies and pushes me to be the best I can be,” she said.

That level of dedication helped Oakley earn a spot on the boys varsity team when she was just a seventh-grader. Knowing that her brother, a sophomore at the time, was also on the team made the transition a bit less intimidating, but she said being a middle school girl on a team of mostly high school boys was still daunting at first. Her pride at her achievement overrode those feelings before long.

“When I was in seventh and eighth grade and I had a ninth or 10th period class, I had to leave early [on match days], and I always felt so much pride standing up in my classroom and getting to leave,” she said. “I felt like I showed my peers that you can really do it if you put your heart into it.”

By her freshman year, Oakley had become the No. 2 golfer on the team, behind only her brother. She earned the respect and admiration of her teammates, for the most part, she said, but added that her opponents sometimes had a hard time accepting her presence — particularly when she beat them.

“Boys on the other teams, you could tell when I beat them that they were upset,” she said.

During matches, players shake hands with their opponent before and after playing. Some of the other players would laugh when their teammate was paired with the only girl, she said.

“All the boys would give this look like, ‘Oh my God, you have to play her,’” she said. “But I would go out and earn their respect. I still have friends from other schools from the boys teams. I gained their respect and showed them that a girl could do this. I showed them it’s not a joke for a girl to play golf.”

Oakley had company on the boys team during her second season with them, when Kaitlyn Browne joined the squad as a seventh-grader, and she said she was thrilled to have a female teammate. The two ultimately became the driving force behind the creation of the Southampton girls team, which has yet to experience a loss in two seasons of play and is likely to be a force again, with Oakley back for her senior season, leading several other talented returning players. Oakley will try to reclaim the Suffolk County Individual title she won in her sophomore year, and will try to help the team earn the county team title as well.

While she enjoyed her time on the boys team, Oakley said the camaraderie she has experienced being on the girls team, and knowing she and her teammates were the driving force behind its creation, has been a thrill.

“Right now, we’re 24-0, and every one of us takes pride in saying that,” she said. “We’re the first girls golf team, and I believe we’re one of the only sports in the school that has been undefeated for two straight seasons. That fact that we’re a new team makes that even more special.”

The feeling of pride that comes from doing something that has never been done is something Oakley experienced again, when she took the job at Shinnecock. She had a connection there, as her brother had been caddying there for three years, and her mother knew the caddymaster. They discussed the possibility of Caraline working there during the early spring of her freshman year. Before long she had the job, and once again experienced the mixture of pride and apprehension at making her way in an environment populated exclusively by men and boys. This time, the stakes were even higher, the history-making moment more profound — she was becoming the first female caddy at a world-renowned club, the oldest incorporated club in the country, one that has hosted the U.S. Open five times and regularly appears on lists of the best golf courses in the world.

“I was definitely on edge at first,” Oakley admitted. “I knew that it’s a very prestigious club, and that it’s a big step to be the first female caddy, and I didn’t know if they were ready to make the step, but I was thrilled that they did.”

Oakley’s father accompanied her to her first caddy meeting, a moment burned in her memory.

“I was the only girl in the whole caddyshack, and everyone’s eyes were following me because it was so out of the norm,” she said. “When they introduced me and said, ‘Here’s Caraline Oakley, our first female caddy,’ I had to stand up, and my face got so red.”

Like she did with the boys varsity golf team, Oakley found a way to fit in quickly, thanks again to fellow caddies — including some fellow students at Southampton — willing to make her feel at home. There are still interesting moments, she says, whether it’s a new caddy not realizing that she works there, or the fact that the caddymaster has to ask any male players if they’re OK with having a female caddy before she’s assigned to them. But by and large, she says the experience has been positive.

“We’re all super close here,” she said. “We play chess during down time, and have great conversations. Everyone accepts the fact that I’m there now, and they have to hold back from saying certain things around me. Boys will boys, and I have a brother, so I’m used to it, but it was eye opening at first.”

Her presence has been largely appreciated and supported by members and players as well, particularly women.

“My first time out, I had a woman who was so nice, and it was her and a group of three other ladies,” Oakley said. “They were so excited that I was the first female caddy, so it was great to have their support.”

Ian Green is in his 20th year caddying at Shinnecock and says that he and his fellow caddies were determined to make Oakley feel welcome from day one.

“Her first day working here, we told her she just inherited 40 big brothers,” he said. “We all looked out for her and treated her with respect.”

He has taken Oakley under his wing in other ways as well, including caddying for her the last two years in the Geary Cup, an annual two-day tournament in June between the caddies from Shinnecock and nearby National Golf Links of America. Shinnecock won the tournament for the first time in years last year, and Oakley was paired with Browne, who caddies at National.

Green says the hiring of Oakley, and the history it made, was a good move for the club.

“It’s about time,” he said. “Golf is for anybody. This is something anybody can play and anybody should be able to work as a caddy too.”

Green says he believes the best is yet to come for Oakley.

“She’s going to do great anywhere she goes because she’s so motivated and has such a great and positive outlook, and because she works for it,” he said. “Her parents should be very proud, which I’m sure they are.”