Frances Middleton told her son that it had been the couple's intent to leave him the cigar company, John Middleton Inc., which his great-great-grandfather had founded in 1857 as a tobacco shop. In the 1950s and 1960s, it became a successful cigar manufacturing company that had built up more than $200 million in revenues by the early 2000s. One of its innovations was rolling pipe tobacco into tipped cigars.