Bobby learned to play golf at Argyle Country Club with a host of good junior golfers and attended Springbrook High School, where he was voted the number one high school golfer his senior year by the Washington Post. He went on to play college golf at the University of Maryland in 1968 and 1969.
After college, he had a brief career in professional golf, spending two summers as the assistant golf professional at the Chevy Chase Club and, in between, one season on the South Africa PGA Tour. After winning 17 events over the course of two years, he was named Middle Atlantic PGA Player of the Year in 1971.
As successful as he was in the 1970s, winning both the Maryland Amateur and Washington D.C. Metropolitan Amateur, among other tournaments, playing golf eventually took a back seat to raise a family and build a business for the next 20-plus years. He found his way into sports management, joining ProServ, an international sports marketing firm located in Washington, D.C. During his tenure there, he represented over 30 professional golfers on the PGA and European Tours, including eight major champions: Payne Stewart, Billy Casper, Raymond Floyd, Gene Littler, Scott Simpson, Nick Price, Kathy Whitworth, and Hollis Stacy. In 1987, he created the Northville Long Island Classic, an annual stop on the PGA Champions Tour.
In 1989, he cofounded Billy Casper Golf Management with Peter Hill. The company owned, leased, and managed over 300 golf course facilities in 30 states over its 32 years in business. By the time the company was acquired in 2020 by Troon Golf, it had become the largest privately-owned golf management company in the country. The company also gave back to golf, hosting thousands of junior golf camps and seven First Tee facilities at golf courses within the portfolio. Well over one million dollars was donated to Wounded Warriors and The Fisher House Foundation through various events sponsored by BCGM.
With business stabilized and five children grown, he went back to competitive golf and rose to be the fifth-ranked senior amateur in the country, holding runner-up and 4th place finishes in the British Senior Amateur. He was also the medalist in the 2004 Canadian Senior Amateur. He is a three-time Maryland State Senior Champion, two-time Washington DC Metropolitan Senior Champion, Middle Atlantic Senior Champion, and Virginia State Senior Champion. He remains the only player in the metro area to have won all 4 area senior championships.
Locally, Bobby has won 12 Maryland State Golf Association titles in addition to being runner-up two times in the Maryland Open. With various partners, Bobby has won more than 25 state, national, and international four-ball championships. His other titles include the Alaska Open, the Dominican Republic Open, the Japan Classic, and the MAPGA Open. He has qualified and played in 10 USGA Championships, 5 British Senior Amateurs, the Canadian Senior Amateur, the Mexico Senior Amateur, 4 Hassan II Moroccan Opens, and 3 European Masters, in addition to the Dutch Open, Leeds English Open, and Italian Open on the European Tour.
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