Donor Spotlight | The Whitford Family

September 20, 2023

by Diane Foote

For Chris Whitford, sailing has always been a family affair. Whitford grew up in Delaware and sailed on the Rehoboth Bay and the Chesapeake Bay with his family, all of whom are lifelong boaters. He first joined the Chicago Yacht Club in 1983 in order to race his Tartan 10, Billy Bones, in the CYC Race to Mackinac. Since then, he has raced in 40 consecutive Races, first on Billy Bones and, since 1999, on his current boat, the Farr 40 Hot Lips. His oldest son Michael has joined him for 22 of those, and now skippers the boat. His younger son Robbie, also a CYC member and a sailing school 420 racer, joined him for the Bi-State Regatta this year, which was Robbie's first port-to-port race. Robbie expects to join the Hot Lips crew for his first Mac in 2024. 

When Michael first began sailing at the age of six as one of the very first participants in the Club's Dinghy Demons program, Chris's relationship with sailing evolved. "I was no longer a sailboat racer," he says, "I was an Opti parent." He cites this experience as a factor in his desire to support broadening sailing opportunities for Chicago's youth: "Through the collective genius of Bill Fox, then head of the CYC Junior Activities Committee, and Chris Mitchell, then head of the sailing school, the sailing school offered a fantastic program. Equally important, they reached out to the entire Chicago community advertising the program and inviting anyone with an interest in learning to sail to come join us." The CYC Foundation's sailing school scholarships seek to make this opportunity achievable for an ever-broader community of young sailors.

Whitford is a longtime supporter of the Chicago Yacht Club Foundation, including the general fund, which supports all our programs, and the Competition Fund, which enables the Foundation to award grants to support applicants' training for and participation in prestigious national and international sailing competitions. "I am keenly interested in the Competition Fund," he says. "Young people are the future of sailing. It's important to get as many young people as possible involved." He takes pride in helping more kids take advantage of CYC's sailing camps and helping develop their big-boat racing experience, noting: "In addition to my son Michael sailing with me I’ve also had the good fortune of having many of the other CYC sailing school graduates join me on Hot Lips. They are an awesome group of sailors many of whom represent the club at national events, and they do very well."

Now, the next generation is taking on the mantle of Foundation supporter. Michael and his fiancee Jackie McDermott are planning a wedding in April 2024, and have identified the CYC Foundation as the focus of their wedding registry. Jackie, also an accomplished sail racer, runs the bow aboard Scarlet Begonias, Hot Lips' neighbor on U Dock at CYC's Belmont Station. They understand firsthand the joys and benefits of boating, and feel strongly that it is important to broaden these opportunities for Chicago youth. Sailing and supporting the CYC Foundation are "all in the family" for the Whitfords!

If you would like to join the Whitford family in supporting the CYC Foundation or to learn more, please visit our website

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From the Helm