Fleming directs and manages Breeders' Cup Limited's general operations which include host track relations, long-term planning and business growth, financial, legal, sponsorships, and marketing.

Fleming spearheads the long term planning and coordination of business opportunities for the company, which administers the Breeders’ Cup World Championships, Thoroughbred racing’s year-ending international event. Among his duties with the Breeders’ Cup, Fleming will be responsible for: enhanced constituent communications within the Thoroughbred industry; legislative support in areas such as safety and integrity issues and gaming initiatives; corporate governance; venture capital opportunities; legal compliance; and risk management.

As a transactional attorney in Stoll Keenon's Lexington office, Drew concentrates his practice on mergers and acquisitions, equine transactions, securities, corporate governance, real estate and banking.Drew has represented clients ranging from individuals to Fortune 500 companies on a variety of corporate issues. He knows the importance of learning and understanding his clients' businesses. Drew's experience working on a thoroughbred farm and being a thoroughbred owner having raced on multiple continents affords him the ability to offer insightful advice to those involved in the thoroughbred industry. Drew routinely represents both domestic and foreign equine clients, including horse farms, trainers, sales companies, racetracks, banks, and organizers of multiple ownership arrangements in connection with the purchase, sale and syndication of thoroughbreds, the acquisition of thoroughbred farms, equine lending, and the corporate structuring of racing syndicates and private placements.Additionally, Drew has represented domestic and foreign clients in mergers and acquisitions ranging in size from several million dollars to several billion dollars in a variety of industries including energy, manufacturing, sports marketing, and banking. He has also represented clients in both venture capital and private equity transactions.