In 1990, Lewis and his wife, Beverly J. Lewis, bought their first Thoroughbreds. They became dedicated owners, spending millions at yearling sales and hiring first class trainers such as Bob Baffert and D. Wayne Lukas. The couple's first major success came when Timber Country won 1994 Breeders' Cup Juvenile then in 1995, the Preakness Stakes. At the same time, their filly, Serena's Song, was voted the U.S. Champion 3-Year-Old Filly for 1995. After retiring, in 2002 Serena's Song was inducted in the National Museum of Racing and Hall of Fame. That year they were voted the Big Sport of Turfdom Award.