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“Having James, and now Teddy ’26, choose Fairfield — and knowing the Catholic values we raised them with are being reinforced — means a lot to us,” said Winnie.

While Winnie and Sean O’Keefe had no connection to ÌìÃÀ´«Ã½ÊÓƵÎÞÏÞÖƹۿ´ before their son, James ’23, applied, it didn’t take long for them to embrace his decision and become Stag fans themselves.

“Having James, and now Teddy ’26, choose Fairfield — and knowing the Catholic values we raised them with are being reinforced —means a lot to us,” said Winnie. She shared that the public schools where the family lives in Bergen County, New Jersey, are very good, so their three boys all went through the public school system and didn’t experience a Catholic education prior to Fairfield.

Winnie O’Keefe has long been familiar with the Jesuit idea of curis personalis — her brothers and other family members attended St. Joseph Prep, the Jesuit high school in her hometown of Philadelphia. In addition to the liberal arts education and values that she recognizes as so important, she and Sean have been impressed by the opportunities presented by Fairfield’s Charles F. Dolan School of Business, where James majoring in finance and accounting. He also participates in the Student Mutual Investment Fund.

“His education both in an out of the classroom has been amazing,” said Winnie, noting that her son has had internships at UBS and Martin DeCruze & Company, an accounting firm in Stamford. Like his brother, Teddy also plans to study finance. Both were attracted to Fairfield’s size and to the beautiful new Dolan School building with its state-of-the-art facilities.

Fortunately for Fairfield, the O’Keefes’ enthusiasm has led them to become actively involved with the Parents Leadership Council. Among other things, they’ve spoken to the parents of incoming students to welcome them, connect them with one another, and to encourage their involvement in the life of the school. On a personal level, Winnie said that involvement has been significant.

“I feel that I’m not just sending my kids off; I can actually make a difference. We can be part of the institution that we’re all so happy with. It’s a great way to get to know the school and the people in it, and when I come to campus I feel connected,” she said. Sean, a director at a large Wall Street firm, and Winnie, owner of Whimsie Luxury Travel, have taken the family on numerous vacations around the country and throughout Europe. With three boys, there are no relaxing Caribbean sojourns for this crew — they can generally be found hiking, camping, and exploring new places. But there’s one spot they return to every year.

“Our happy place is Ocean City, New Jersey, where we meet up with extended family,” said Winnie. “All the cousins are the same ages, and it’s a family tradition for everyone to descend on OC over the July 4th weekend.”

Giving back is another family tradition, dating back to Winnie’s grandfather who always donated generously to the high schools and colleges with which the family has connections.

“We’re grateful that the family has supported both financial aid and technology upgrades for students in the Dolan School,” said Fairfield’s Ellen Dooley ’85, P’23, director of parent engagement and philanthropy. “Besides establishing a scholarship, their donations have helped to keep the hardware and software in Dolan’s Trading Simulation Floor and Financial Laboratory up to date, so that business students can practice using the technology they’ll need when they step into their jobs.”

“Sean and I understand the importance of supporting the educational institutions and the organizations that support our values,” said Winnie. “We encourage other parents to get involved in any way that interests them, because it feels great when you do, and it can make an invaluable difference.

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