Tom Simpson started his collecting career with a pack of baseball cards in Meigs, Ga., in the 1950s. They came in wax packs—five cards plus a slab of Pepto-Bismol pink bubble gum. A nickel bought you a trip to collector nirvana if a Mickey Mantle or Willie Mays card appeared.
Sadly, the baseball cards of his youth were destroyed or lost. But rather than try to rebuild his old card collection, Mr. Simpson has, over the ensuing years, created a trove of sports, music and other types of memorabilia that he has arrayed throughout the 25,000-square-foot property he shares with his wife, June Simpson, in Thonotosassa, Fla., outside Tampa.