Caddyshack to Corner Office

Recognizing the most accomplished people who once caddied and growing the game by assisting those following their path


As Seen In

Kai Sato Kai Sato

Official Caddying Story: Zach Kuperman

Zach Kuperman has extensive experience managing the insurance portfolios of hospitality companies across the country. As a Senior Vice President at Hub International, he is a leader in the National Hospitality Practice and works directly with brands such as CapitalSpring, Mendocino Farms, Lazy Dog Restaurants and many more leading restaurant operators/franchisees. Zach has extensive experience helping restaurant operators build out safety programs, risk management platforms and migrate to alternative risk insurance solutions. Prior to his work in the insurance industry, Zach worked in the banking and technology industries before touring the country for seven years as a stand up comic. In his spare time, Zach now enjoys fishing, being outdoors with friends and of course obsessing about missing his last three foot putt on the golf course.

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Kai Sato Kai Sato

Official Caddying Story: Dick Connolly

Dick Connolly is an accomplished Private Wealth Advisor who has managed investment portfolios for several decades. He has built his business by providing sound investment advice to high net worth families, foundations, nonprofit organizations and other financial institutions. Dick’s reputation as an investment manager in Boston has been earned through many years of hard work and dedication to his clients. He is firmly committed to fostering long-term relationships and strives to deliver exceptional client service. Dick began working as a financial advisor in 1969 at Paine Weber, where he spent the majority of his career. Dick is a graduate of The College of Holy Cross and earned his MBA from Babson College. He is a member of Morgan Stanley’s Chairman’s Club. Dick has been married to his wife, Ann Marie, for 35 years. They have three sons and live in Concord, Massachusetts.

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Kai Sato Kai Sato

Official Caddying Story: Corey Pavin

Corey Pavin needs no introduction. The winner of the 1995 US Open at Shinnecock Hills, he won 15 tournaments on the PGA Tour and also topped its money list in 1991, garnering Player of the Year honors from the PGA of America. He also won over a dozen tournaments as a professional on other tours around the world. He was the captain of the Ryder Cup in 2010, having previously been a 3-time participant on the US team. He also competed on two Presidents Cup teams. In college, he was the NCAA Player of the Year and a member of the Walker Cup. Now a member of the PGA Tour Champions, he’s been named to various halls of fame, in recognition of his many accomplishments in golf. What few people know, however, is that Corey helped put himself through college by working as a caddie. 

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Kai Sato Kai Sato

Official Caddying Story: Fred Gaudelli

Fred Gaudelli is the executive producer of NBC’s Sunday Night Football , but his very first job was as a caddie. In January 2021, he completed his 31st season as the lead producer for an NFL primetime game, and his 15th season producing SNF. In August 2020, Gaudelli was honored as a member of the Sports Broadcasting Hall of Fame’s Class of 2020 for career-long excellence in the sports TV and media industry. A 23-time Emmy Award winner, Gaudelli’s five prior Super Bowls (XXXVII, XL, XLIII, XLVI and XLIX) include Super Bowl XLIX, which still ranks as the most-watched program in U.S. TV history with an average of 114.4 million viewers. Gaudelli introduced the critically acclaimed 1st & Ten technology, the electronically produced yellow line that appears to be painted across the field at the first down marker, the GoalPost Cam and the rotating clock/score box. Additionally, while working at ESPN and producing the 1988 College World Series, Gaudelli introduced the technique of live tracking the speed of pitches – a first on television. A native of Harrison, N.Y., Gaudelli earned a Bachelor of Arts degree in communications from Long Island University/C.W. Post in 1982. He currently resides in Madison, Conn., and has a daughter, Reese.

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