(Read more: JC Penney board erupts into fight over next CEO)
But 100 years makes for one long bet, particularly on a player in a sector as flighty as mass-market retailing, and it's been anything but smooth sailing since.
Like the stock, Penney's bonds, long since fallen deep into junk status with a CCC- rating, have taken it on the chin as the store group's sales have plunged amid a disastrous pricing and marketing strategy and failed attempt to appeal to the more affluent shopper. Its recent related tussle with activist hedge fund investor Bill Ackman, and uncertainty about the status of its vendor financing deals, have further undermined investor confidence.
It is now facing a very uncertain holiday season with a temporary CEO at the helm following its firing of Ron Johnson, the former Apple executive who was largely seen as the architect of its failed strategy.
The 2097 bonds have fallen 21 percent in price since mid-May, and currently are trading at 67 cents on the dollar, near their lowest since the financial crisis. They offer a yield of 11.38 percent. By contrast, the average effective yield on bonds in the Bank of America Merrill Lynch CCC and Lower U.S. High Yield Index, an index of lower-rated junk bonds, is 9.77 percent.
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Some big names in the bond business can be counted among the casualties.
Loomis Sayles & Co. holds about $19.4 million of the bonds as of June 30, according to Emaxx, a bond investor tracking service owned by Thomson Reuters.
Dan Fuss, vice chairman and portfolio manager at Loomis, said the firm, which has $190 billion in assets, is reassessing its position.
"When you lose market share, it is difficult to stop the bleeding, especially in retail," he said.
Back in 1997, the Penney deal came to market in what turned out to be the banner year for "century bond" issuance.
(Read more: 'Just a couple of quarters' left for JCP?)
Following on IBM's record $850 million deal in December 1996, ultralong-bond fever struck Wall Street and corporate treasurers alike, and an unprecedented 26 investment-grade century bond sales totaling $7.12 billion hit the market over the next 12 months, according to IFR Markets data.
Car makers Ford and Chrysler both sold $500 million, as did Baby Bell operators BellSouth and US West. Railroads Norfolk Southern and Burlington Northern Santa Fe clocked in at $350 million and $200 million, respectively, and Boston University raised $100 million.
In all, IFR data shows 65 U.S. 100-year bonds with a face value of $16.29 billion have been issued since Walt Disney and Coca-Cola debuted century deals on successive days in July 1993. Recent ultralong issuance has been dominated by high-rated universities, which account for six of the 10 deals since the financial crisis, led by Massachusetts Institute of Technology's $750 million deal in May 2011, largely on the basis that they are more likely to be around in the next century than many companies.
(Read more: Citi downgrades JC Penney stock to 'sell')
In fairness to Penney's bonds, few of the century bonds have fared well of late as the corporate bond market has been whipsawed by investor anxiety over the future of the U.S. Federal Reserve's massive stimulus program.
High-grade bonds like IBM's 2096s, rated AA-, have dropped 18 percent in price since early May. Even MIT's AAA-rated notes due 2111 have shed 19.3 percent in price in that time, with their yield climbing nearly a full percentage point to 4.88 percent.
Still, the questions around Penney's future suggest more volatility ahead. Its credit default swaps, insurance against a default, price a nearly 65 percent default probability in five years and 85 percent over 10 years, according to data from Markit. For some bond mavens, that's just too much risk to take on.
Portfolio manager Bonnie Baha, who heads Global Developed Credit at DoubleLine, said the $57 billion bond house has had Penney bonds on its "avoid" list for years and doesn't buy the argument that Penney's swooning securities don't take into account the value of the retailer's real estate.
"In the era of Amazon.com and other online retailing, I don't think much of legacy real estate assets of the Big Box stores," Baha said.
