Barry McLaughlin
General Manager | Email Barry

2021-Present: General Manager, Chequessett Club
2002-2021: Executive Director of The First Tee of Metropolitan New York and General Manager of the Mosholu Golf Course. During Barry’s nearly two decades of service, the youth development organization and nine-hole golf course in the Bronx thrived to be one of the top Chapters in the country. The Chapter grew to support the entire tri-state area with a total of six locations (Mosholu (NYC), Fairchild Wheeler (CT), Chelsea Piers (NYC), Eisenhower Park (LI-NY), Essex County-Newark (NJ) and Plainfield West Nine (NJ) serving of 15,000 participants annually.
OTHER COMMUNITY RELATIONSHIPS AND COMMITTEE INVOLVEMENT:
- Board Member, First Tee New York, Inc.
- NYU Scholarship Committee Member
- Nyack College Scholarship Committee Member
- Chairman of the Gala Committee (10th Anniversary Gala) First Tee New York, Inc.
- Secretary, Norwalk Little League
AWARDS & RECOGNITION:
- Recognized The First Tee Executive Director
- Community Service Award, VISIONS (Services for the blind of New York City)
- Community Service Award, Special Olympics (NYC and Fairfield County)
- World Golf Foundation, Chairman’s Award 2007
Tracy Dean
Director of Events, Membership & Sales | Email Tracy

Tracy is originally from NY, spending summers on Cape Cod. Prior to Chequessett, Tracy has been a custom interior designer for the last 2 decades, during which she owned her own design firm for 8 years. Moving to the Cape full time, Tracy has enjoyed working as a Membership & Events Director here at the Club. Whether you’re hosting a wedding reception, an anniversary, a birthday, or a special occasion event, Tracy will carefully craft every detail with the upmost care to ensure your celebration is everything you dreamed it would be. She has a great appreciation for art and architecture and an unconditional love for her family and friends. Tracy and her husband Frank reside in Eastham.
Calvin Dees
Head Tennis Professional | Email Calvin

Calvin Dees has been a certified USPTR Tennis Professional since 1997 and has more than 20 years of teaching experience. He earned his bachelor’s degree in physical education from Winston-Salem State University and played competitively in USTA tournaments for over 20 years as a junior and young professional. He continues to play competitively in two USTA leagues and is rated as a 4.5 level player. During the indoor season, Calvin teaches adults and juniors of all skill levels at Bloomfield Tennis Club in Connecticut. He has successfully coached his junior tennis team to the national championships two years in a row.

