The other pillar of Fleming’s life, aside from romantic liaisons, was his business ventures. Originally a salesman, he eventually filed a wrongful termination suit against the American Tobacco Company for $19,000 (a hefty sum in that time), and used that money, partly out of spite, to form his own tobacco company in Detroit – Red Devil Tobacco – and use the proceeds to post propaganda all around the city besmirching American Tobacco, claiming they abused workers and were anti-union. In the current political climate, this whipped Detroit up into a frenzy, until James Duke, owner of American Tobacco, bought Fleming’s company out and discontinued the brand to save his company’s good name, putting huge sums in Fleming’s coffers in the process. At the time, the average wage everyman was desperately pro-Union, because unionizing was the only hope for fair pay for many workers, so Fleming's propaganda was so effective that, by 1939, the company had fully embraced a partnership with a Tobacco workers union (Traver 5). Eventually, the American Tobacco company would fall completely, but not to Fleming - to the Sherman Anti-Trust Act, which broke up James Duke's conglomerate fully in 1911, and left only a shell of the same name operating solely in North Carolina.
James Duke, owner of the American Tobacco Company
For a while, Fleming reaped the rewards of his work, but eventually a stroke of bad luck ruined him. He invested heavily in real estate in Florida, which was destroyed during a flood (likely due to the Okeechobee hurricane in 1928), and left him penniless, forced to live in a rundown shack in Milton, next to what used to be his childhood home, now turned into a post office.
However, by the time of the interview, Fleming seemed at peace with his state of affairs, happily remarking that he wasn’t afraid to die, and was happy to have lived a full life, full of romance, pleasure, and prosperity. Strangely enough, he seemed particularly pleased that his body would be cremated, which was an almost unheard of practice at the time. Even thirty years later, in 1969, it only accounted for 4.4% of deaths. In closing, he remarked how happy he was that, after a long and full life, his ashes would be "placed in a little bronze box and brought back to lie in the old Milton cemetery, beside [his] mother's grave" (Cannady).
"1928 Okeechobee Hurricane.” Wikipedia, Wikimedia Foundation, 18 Feb. 2017, en.wikipedia.org/wiki/1928_Okeechobee_hurricane.
Cannady, Beth. “John Fleming: Southern Gentleman," in the Federal Writers' Project papers #3709, Southern Historical Collection, The Wilson Library, University of North Carolina at Chapel Hill.
Carter, Robert W. “American Tobacco Company.” American Tobacco Company, NCpedia, 1 Jan. 2006, www.ncpedia.org/american-tobacco-company.
Edmands, Michael J. "Dying Business?" Barron's National Business and Financial Weekly (1942-Current file), Aug 25 1969, pp. 5. ProQuest Central, http://search.proquest.com/docview/350459022
Frank Traver, DE V. "THE PRESENT STATUS OF LABOR UNIONS IN THE SOUTH." Southern Economic Journal (pre-1986), vol. 5, no. 4, 1939., pp. 485 ProQuest Central, http://search.proquest.com/docview/217134211
Stave, Bruce M. ""the Doctor Told Us what He Wanted": Sam Koenig's Instructions to WPA Ethnic Group Survey Interviewers." The Oral History Review, vol. 34, no. 2, 2007., pp. 17 - 25 ProQuestCentral, http://search.proquest.com/docview/223527544
Strow, Claudia W., and Brian K. Strow. "A History of Divorce and Remarriage in the United States." Humanomics, vol. 22, no. 4, 2006., pp. 239-257 ProQuest Central, http://search.proquest.com/docview/203018236
“169 Broad Street, Milton NC.” Homes and Land, images.npmg.io/images/c4b9f37e5d5b29eb4f56ea664d0937cd/scale?w=640&c=l.
“American Tobacco Company Plant in Durham, NC.” Open Durham, Google Images, www.opendurham.org/sites/default/files/images/2008_3/americantobacco_1870s_2.jpeg.
“Early 20th Century Couple.” Google Images, blog.neu.com/wp-content/uploads/2011/09/bm-2.jpg.
“James Buchanan Duke.” Wikipedia, Wikimedia Foundation, www.opendurham.org/sites/default/files/images/2008_3/americantobacco_1870s_2.jpeg.
“Labor Day Parade.” Industry Weekly, Google Images, www.industryweek.com/site-files/industryweek.com/files/imagecache/galleryformatter_slide_penton/gallery_images/1903-WTUL-Float-Labor-Day-Parade-NYC.jpg?1403799359.