Ironically, there actually was one irresponsible Jazz Age aspect to the J. C. Penney story. It involved the founder himself. Remember that for every new store that opened, James Cash Penney received (in effect) his cut. This translated into vast holdings of J. C. Penney stock, and the founder became a fabulously wealthy man. But no tragic Fitzgerald character ever spent more money with such reckless, self-absorbed abandon than Penney. Originally, of course, he had been quite thrifty and, in later life, he was well known for his parsimony. But nowwithout a drop of alcohol involvedhis was a Jazz Age story to make one weep.
James Cash Penney was featured in newspaper and magazine articles. A best-seller was published about his career, The Man with 1,000 Partners . Because of the company's broad middle-class orientation, no other businessman approached Penney's popularity. And there was an egalitarian aspect to Penney's success as hundreds of other men mainly store managersalso grew rich because of the opportunity he afforded them. Largely operating in small towns where they lived modestly, they retired quietly to places like Delray Beach, Florida, and only upon their deaths did anyone beside their bankers realize the size of their fortunes.
The national convention in 1925 would be the company's last (before year 2000) because of the organization's growing size. Henceforth, conventions would be held region by region, requiring senior management to be on the road for a month. This presaged another company redefinition on the horizon. It would take a while for this new identity to be fully defined, but the J. C. Penney Company had outgrown its status as a regional chain. It was well on its way to becoming America's Main Street merchant.
And Penney rode the gathering wave.
After an intense period in the early 1920s working on personnel and training, Penney himself spent less and less time with the company, having been seduced by the boom times and the power of his signature. With bankers eager to lend against his immense stock holdings, he began an attempt to build a second fortune through cattle breeding. (The barns at Penney Farms in upstate New York were designed by a renowned architect.) He built a country estate, a Florida mansion, and an entire village for retired ministers. He bought Missouri farms and great tracts of Florida land.
From art on the walls to jewels in the safe to entertaining opera stars and heads of state, the Penneys  led a celebrated life. In New York during the week, they resided in a 17-room Park Avenue South co-op with a live-in staff of five plus a full-time chauffeur. In addition to moving between residences, the Penneys traveled widely abroad with a retinue of servants. And, at all times, Penney directed greater and greater amounts of money toward more and more church -oriented charity. Consequently, toward the end of the 1920s, Penney's company activities had become limited to occasional speeches and ceremonies.
 Penney married Mary Kimball in 1919 and lost her to illness in 1923. He married Caroline Autenrieth in 1926 and remained contentedly with her until his death in 1971. There were children from both marriages.