Pippy O’Connor and Ginger O’Shea

The two women who led the way for independent school girls golf

by Bob York

There’s a trophy to be found somewhere on the island of Bermuda, but only the gods of golf are certain of its whereabouts. Its hideout is rumored to be in or around the clubhouse of the Mid Ocean Club in affluent Tucker’s Town, located along the northeastern tip of the isle where it was won back in 1955.

Yet here we are, nearly three-quarters of a century later, and that token for the Bermuda Ladies Championship remains homeless. It’s not that its champion, “Pippy” Rooney, shunned it, but rather was reluctant to return to her home in the Boston suburb of Jamaica Plain with spoils in hand.

The hesitancy, according to Ginger O’Shea, Rooney’s “second or third cousin,” was due to the inscription on the trophy. “The tournament directors engraved ‘Pippy’ on it,” explained O’Shea. “Pippy’s the name she preferred. The problem was that her real name was Theodora — the name her parents preferred — and she was afraid to show it to them.”

And so, Theodora Catherine ‘Pippy’ Rooney O’Connor’s 1955 Bermuda Ladies Championship Trophy only adds to the lore of the infamous “Bermuda Triangle,” where countless ships and airplanes and at least one trophy have seemingly vanished forever.

“Pippy told me about the trophy and why she left it behind,” said O’Shea. “She never admitted to me that she wanted the trophy, but when my husband and I went to Bermuda on vacation a few years later, I thought it would be cool to find the trophy and bring it back home to her, if possible. And if not, I figured I could at least take a picture of it for her.

“As it turned out, we searched every trophy cabinet in the clubhouse,” added O’Shea, “but were unable to locate it. I guess I should have inquired further about it, but I didn’t. If I should ever get back to Bermuda I will do further investigating because her son Ted has nicknamed one of his daughters “Pippy” and it would be so nice to be able to give that trophy to her.”

It’s not as if the grandkids don’t have anything to remember O’Connor’s golfing exploits by, however. Even without the Bermuda trophy, there are still plenty of mementos that O’Connor, who died in 2016 at the age of 86, managed to bring home that exhibited the magnitude she showed on a golf course.

She was the 1948 Women’s Golf Association of Massachusetts Junior Champion and won the Massachusetts Women’s Amateur crown in 1955. Those conquests are accompanied by being crowned the Women’s Club Champion of the Charles River Golf Club in Newton no less than 11 times; over in Scituate, she was a seven-time women’s champ at the Hatherly Country Club.

O’Connor was also a three-time qualifier for the U.S. Women’s Open and in 1955, was one of a few qualified amateurs who were invited to compete among the Ladies Professional Golf Association ranks and did quite well for herself. In fact, she competed against such fabled women golfers as Patty Berg and Mildred Didrikson better known as “Babe” Didrikson Zaharias during her stint in the LPGA and defeated them both. Her legend on the links eventually led her to be inducted into the New England Women’s Sports Hall of Fame in 2000.

Despite her success on the LPGA circuit, O’Connor opted not to turn professional and her reasoning for remaining on the amateur level was revealed following her Hall of Fame induction.

“I realized I loved teaching and got great satisfaction out of helping others,” O’Connor told The Boston Globe. “You had to give up everything to reach the top level and I wasn’t sure I wanted to do that. I just wanted a normal life.”

Despite never having won it, there’s one particular trophy that has O’Connor’s name chiseled on it that she came to cherish more than any other and that would be the trophy annually presented to the winner of the Pippy O’Connor Independent School Girls Golf Classic.

“That was Pippy’s dream,” said O’Shea of the annual tourney that has become one of the biggest independent school-age girls golf summits in the country and one of the longest running as well. The tourney’s 37th rendition hit the fairways of the Watertown Golf Club, adjacent to the Taft School campus in Watertown, Conn., on May 8. Phillips Exeter Academy (329) won the team title, edging Taft (332) for the crown by just three strokes. Greenwich Academy (350) finished third, while Sacred Heart (369) and The Winsor School (372) rounded up the top five finishers, respectively.

Overall, 111 girls representing 21 prep school teams took part in the tourney, as 72 girls signed up for the highly competitive 18-hole division, while 39 took part in the 9-hole division, which mainly features freshmen and sophomores, as well as middle-school golfers.

Morgan Smith of Phillips Exeter Academy carded a 74 to finish atop the 18-hole division, while Taft’s Cindy Cao was one stroke off the pace (75) to place second. Sofie Robinson of Wilbraham-Monson Academy carded a 77 for a third-place showing, as Annie Dai of Northfield Mount Hermon School, Lucy Wang of Middlesex School and Angelina Gong of Exeter tied for fourth place as the trio finished with identical 78s.

In the 9-hole bracket, Cushing Academy’s Angie Yu led the field with a 41, while teammate Ophylia Li wound up second with a 43. Taylor Horgan of Westminster School carded a 45 to earn her a third-place finish, while Tiffany Sun of Exeter and WillistonNorthampton School’s Mayphie Zhou tied for fourth place as both finished the day with a 48.

“Pippy started this tournament single-handedly back in 1986,” explained O’Shea, who is not only O’Connor’s cousin, but has also been serving as the director of the O’Connor tourney since O’Connor stepped away from the job in 2006. “That was the year we renamed the tournament in Pippy’s honor. We felt it was only fitting, seeing what an extraordinary ambassador she had been for the game of golf … especially for girls.”

O’Shea, who stepped down as the tournament’s director following this year’s awards ceremonies and who also retired as the Taft girls’ golf coach after this season’s Founder’s League Championship Tournament following 17 years at the helm, pointed out that O’Connor was the first person to create an independent school girls golf program in Massachusetts, when she founded a team at Noble and Greenough School back in 1983.

The rookie mentor quickly discerned the first hazard she would be facing would have nothing to do with water, woods or sand. It would have to do with competition — or the lack of it. Opponents at that time were limited to girls who played for public high schools and who were members of the Massachusetts Interscholastic Athletic Association. Girls who attended independent schools were not members of the MIAA and thus were not eligible to compete in the Massachusetts Girls High School Golf Championships.

“Pippy thought this was unfair and so she decided to create a separate and distinct tournament for girls from independent schools,” said O’Shea. “I’ve been honored for the past 17 years to keep Pippy’s dream, love and spirit alive. Keeping the opportunity for junior girls to play golf and compete in a friendly, yet social and competitive environment had been Pippy’s dream and I just tried to be an extension of the amazing foundation she built.

“My 41 years of teaching and coaching and running the Pippy O’Connor Tournament have proven to be very meaningful because I was very close to Pippy,” added O’Shea. “I had the opportunity to play golf with her and my mom a few times and I will never get those days back, so being involved in this tournament kept me connected to two very influential and important role models in my life.”

In “A History of The Independent School Girls’ Golf Classic,” O’Connor wrote, “our competition in 1984 was mainly the public schools of Brookline High and Duxbury High, while Tabor Academy in Marion, Mass. started a girls’ team in 1985, which included Lauren Milhench, the 1983 WGAM Junior State Champion.

“According to MIAA rules, Milhench, in spite of being the state junior champ, would not have been eligible to play in its tourney because she represented an independent school,” continued O’Connor. “I thought that this was not fair and so I decided to create a separate and distinct tournament for girls from independent schools from within the state.

“I started my first tournament in 1986,” she went on, “and it has grown from a simple nine-hole tournament to one in which the better players compete in an 18-hole tournament, while the younger, less-skilled players compete over nine holes.” And today, the tourney’s field of golfers has grown to represent NEPSAC schools from throughout the New England area.

“The number of competitors in this tournament has basically remained about the same throughout the years,” said O’Shea. “What has changed, however, have been the girls’ skill levels. I can remember when 60 girls would take part in the less competitive nine-hole division, while 40 signed up for 18-hole affair.

“Today, the trend has just about reversed itself,” added O’Shea, who has been recognized in “Who’s Who Among America’s Teachers” for her contributions to the Taft athletic community. “Now we have about 60 golfers competing in the 18-hole event, while 40 now register for the nine-hole event.

“Keeping it in Pippy’s spirit, we’ve made this tournament both welcoming and fun,” said O’Shea, who, like her cousin, is also quite familiar with the business end of a golf club. In fact, O’Shea culminated her final season as mentor of the Rhinos this spring with an undefeated 15-0 record, which gives her a final regularseason showing at Taft of 194-28-8 since she started the program back in 2006. During that span, her girls have captured five New England (O’Connor Tournament) titles as well as five second-place finishes while registering six individual tournament champions. As far as Founders League championships are concerned, O’Shea’s final day on the job saw her Rhinos chalk up their 10th tourney title under her reign.

Taft’s girls’ golf guru was nowhere to be found during this year’s Founders affair, however, as another sport she had mastered over the years was receiving her full attention: volleyball. O’Shea had a prior engagement that same day at the fabled Winged Foot Golf Club in Mamaroneck, N.Y., where she was inducted into the Masters School Athletic Hall of Fame after her volleyball teams there chalked up a 394-53 showing during her 14-year (13-season) span. In 2001, O’Shea would move on to Taft, where she coached varsity volleyball for 17 years, stepping away from the program after having led her teams to 501 career victories and a No. 2 ranking in New England. Her volleyball teams at Masters and Taft combined to win 895 games.

“I feel both truly blessed and fulfilled as far as my time here at Taft is concerned,” said O’Shea. “During a recent Alumni Day, I can’t tell you how many of my former players came back here from all parts of the country to personally tell me how much they felt having played for me had helped make a difference in their lives … as a coach, that’s about the greatest compliment you can receive.

“There were others who couldn’t make it back here,” added O’Shea, “but many of them sent flowers to say ‘Thank You!’ As I said, ‘I feel truly blessed and fulfilled for my time here.’”

Speaking on behalf of the school’s athletic department, Taft Athletic Director Andy Dunn said he too felt blessed to have been able to have worked with O’Shea, even if it had only been for the past two years.

“Ginger has long been a phenomenal advocate and mentor for girls,” said Dunn, “and I guess I can speak for everyone here when I say I consider her retirement as a bitter-sweet moment for Taft School.

“I’m sad to see her go, as I know everyone associated with this school is,” added Dunn, “but I’m also happy to have had the opportunity to have worked with Ginger and to have seen the positive impact she has had on everyone here … she’ll be truly missed by all.”

That feeling of loss begins right at the tippy-top of the NEPSAC food chain, too. It starts with Martha Brousseau, the NEPSAC president and Greenwich Academy athletic director.

“In recent years The Pippy O’Connor Tournament and Ginger O’Shea have become nearly synonymous!” said Brousseau. “Ginger’s tireless and spirited leadership in all things golf has been monumental for those who have participated in “The Pippy” be it the nine-hole or 18hole tournament. Securing great facilities and being the ultimate MC at these events, it was clear to anyone who attended that Ginger was there to promote the game of golf … and it didn’t hurt that Taft wasn’t too shabby from tee to green! Thank you coach O’Shea or all you have done for NEPSAC golf.”

Sue Cabot, the athletic director at archrival Loomis Chaffee echoed those same feelings about O’Shea when she said “Thank you for all you have done to support girls’ golf in the NEPSAC! The growth in numbers and increased competitive field is fantastic. It is such a tremendous opportunity and experience for the golfers. It’s a testament to your commitment to enhancing opportunities and the play of golf to young girls.”

It was also easy to see that Dave Hinman, the coordinator of the Health & Wellness Program as well as the head varsity basketball coach at St. Sebastian’s, was another big fan of O’Shea’s when he said, “Ginger’s work with students and athletes over her career has been exemplary, but her efforts promoting girls’ athletics has been truly outstanding. We are all in a much better spot today due to her tireless effort to create opportunities for our athletes. The Pippy O’Connor Tournament is one such example of many.”

Ann Pickrell, another pioneer of NEPSAC girls golf, was sad to see a longtime colleague, “but more importantly, a valued friend,” head off for a well-deserved retirement. “Ginger and I go back a long ways,” said Pickrell, who established a girls golf program at Williston Northampton School in 2003 and who has also been coaching girls field hockey at Williston for the past 30 years. “I worked with Ginger in a number of different capacities throughout the years, especially at the O’Connor tournaments.

“Ginger’s always been passionate about golf, she’s always been driven to help players improve their game and to compete at the highest level possible and you could see her love for the game come through when it came to directing the O’Connor tournaments,” added Pickrell, whose day job at Williston is that of assistant head of school. “Except for the weather, she always had everything under control.”

As for those annual O’Connor tournaments, don’t let all that “welcoming and fun” stuff fool you, because, as O’Shea put it, “It’s a very competitive tournament, especially the 18-hole division. The girls who compete in this tourney are looking to play collegiate golf … especially the seniors and this gives them the opportunity to see how they stack up against their peers. Plus, it gives college coaches and scouts a chance to watch the best prep school girl golfers in New England all in one place.”

The tourney also allows independent (middle) school age golfers such as Allison Eleey to compete, as the Quincy native participated in the O’Connor tournament as a sixth-, seventhand eighth-grader. “I always looked forward to competing in the Pippy O’Connor tournament, it was always the highlight of our season … at least I looked at it that way,” said Eleey, who took part in six tourneys before graduating from Taft in 2012. “Ever since I was 10 or so, my dream was to play college golf and you knew you’d get plenty of exposure playing in the O’Connor tourney because it always attracted the best female golfers throughout the New England prep school ranks.”

And play well she did. During Eleey’s time on the Taft varsity, during which she was named Player of The Year as a senior by The Boston Globe All Scholastic, she is one of just two competitors to ever capture back-to-back titles of this coveted tourney, leading the pack her junior and senior years (2011 and 2012). Kelly Robb of The Middlesex School, meanwhile, won the tourney as a freshman and sophomore (2000 and 2001) before closing out her career by winning her third crown — the most ever by a single competitor — as a senior (2003).

Eleey, who went on to successfully compete on the Div. III collegiate level at Sewanee, The College of the South, helped her Tiger teammates earn their first trip ever to the Nationals her senior season, where they placed seventh. The trip also followed a season in which Sewanee finished second in the Southern Athletic Association and maintained a Top-10 national seeding throughout the entire 2016 campaign.

Despite the decade that has passed since her final Pippy appearance, Eleey still fondly remembers one of the highlights of competing in the tournament: getting to meet with the tourney’s namesake.

“Pippy O’Connor always made it a habit during the tournament to meet and greet each and every competitor,” said Eleey. “The staffers would drive her around to every hole to meet with us. Pippy was always so gracious, always complimenting us for playing in the tournament and wishing us all ‘the best of luck’ … she never missed anyone.”

Meeting the First Lady of independent school girls golf was also the first highlight that came to mind for Caitlin Sullivan, who won the tournament championship in 2002 and who finished third the following season while representing The Winsor School of Boston.

“Pippy was such a wonderful woman,” said Sullivan, who went on to play “the fourth or fifth position at Princeton University for four years. I still remember the pep talks she would give the players as she would make her way around the course in a golf cart. She would drive over to each competitor and urge them to ‘keep up the good work’ and then wished all of us ‘good luck’ before driving off to greet the next group. Pippy was a special woman … we owe her so much.”

When asked what she thought her cousin might think about how her tournament has carried on without her, O’Shea briefly pondered then responded with, “I think she’d be thrilled looking down and watching her girls having the opportunity to play in yet another of these competitive tournaments.

“I can’t help but think she’d be smiling down on us, too,” added O’Shea. “This year’s tournament was played under rather windy conditions, but it was also a warm and sunny day. Those were the conditions Pippy most enjoyed playing in. She always loved playing golf under the warmth of the sun, but she never minded whenever the wind would pick up a bit, either. She always felt it was Mother Nature’s way of challenging her.”

Last school year was a first for bBIG Live and we produced 341 live games providing NEPSAC families, fans, alumni and coaches with professional live broadcast coverage and postgame film. For those that are not familiar with our services here are just a few of the benefits:

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