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By Dan Burns

Aug 14 (Reuters) – It was a “century” deal, but in hindsight

it was hardly the deal of the century.

More than 17 years and a dozen credit downgrades ago,

JCPenney Co Inc. joined an elite club in capital markets

circles by issuing a rare 100-year bond.

The deal from Penney, then sporting a mid-range

investment-grade rating of “A” from Standard & Poor’s and coming

off record holiday-season sales, matched the year’s largest

“century bond” deals at $500 million, but the company stood out

as the only retailer in the mix.

By all accounts the sale of the 7-3/8 percent notes due 2097

, managed by Credit Suisse, JP Morgan, Morgan

Stanley and Merrill Lynch, went smoothly. The future seemed

bright: Penney was riding high on investor optimism about its

$3.3 billion purchase of the Eckerd drug store chain months

earlier and within 18 months its stock would be at then record

highs.

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 are currently 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.

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,” Fuss said.

Back in 1997, the Penney deal came to market in what turned

out to be the banner year for “century bond” issuance.

Following on IBM’s record $850 million deal in

December 1996, ultra-long 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 ultra-long 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.

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.