Guaranty Financial Group Inc., which raised $600 million in July from a group that included the financier Carl Icahn, will probably need another infusion, observers said. But finding investors will be harder this time around.

Last week the $15 billion-asset Guaranty said it expects to report a $444 million loss for last year, including $187 million lost in the fourth quarter.

The Austin company also said it will not file the results on time, because it is reviewing its mortgage-backed securities portfolio. If that review finds other-than-temporary impairments, Guaranty said, it may need to raise more capital.

In addition, observers said its thrift has been charging off soured mortgages at a much slower pace than most other institutions, so bigger credit losses are likely in store.

"Guaranty Financial Group represents the equivalent of a financial black hole," said John Carusone, the president and chief executive officer of the Hartford, Conn., consulting firm Bank Analysis Center Inc. "The bottom is unknown to the investor. It may be well known to management, but not the investor."

Guaranty's stock has dropped about 90% since June. It closed Friday at 90 cents a share.

Carusone said investors like Icahn and Robert Rowling, who also participated in the July capital infusion, might be leery of another round of fund raising.

"That was before the meltdown, and going to the well a second time is infinitely more complex for an institution like this," Carusone said. "It's not impossible, but it's very difficult, and the existing shareholders will be very diluted."

A spokesman for Guaranty would not discuss the losses or the company's plans for raising capital. Icahn's secretary said he was unavailable for comment last week. Rowling did not return a phone call.

During a conference call in November, Kenneth Dubuque, then Guaranty's chairman and CEO, said it was "looking closely at the availability of capital" through the Treasury Department's Capital Purchase Program.

He resigned that month. John T. Stuart 3rd, a director, became the interim chairman and CEO; a successor has not been named.

Guaranty has not reported a quarterly profit since it was spun off from the Austin conglomerate Temple-Inland Inc. in late 2007. In December it said it would cut 250 jobs, or 10% of its work force, and it sold its insurance arm for $40 million.

The spokesman confirmed last week that Guaranty has discontinued mortgage warehouse lending.

According to the Federal Deposit Insurance Corp., at yearend the thrift had a total risk-based capital ratio of 11.33% and a Tier 1 risk-based capital ratio of 8.45%. Both figures were above the regulatory thresholds for being considered well capitalized.

However, Matthew Anderson, a partner at the Oakland, Calif., market research firm Foresight Analytics LLC, said Guaranty does not appear to have been as aggressive as other financial institutions in charging off nonaccrual residential mortgages. According to his firm's analysis of FDIC data, last year Guaranty charged off just 9% of the $232 million of single-family loans it held in nonaccrual status; the national average chargeoff rate for all banks and thrifts was 45%.

"From where they are at in the fourth quarter, I would expect to see more chargeoffs ahead for nonaccrual loans," Anderson said. "And if the loan portfolio worsens, you could see more nonaccruals pile up."

According the FDIC, last quarter nonperforming assets as a percentage of Guaranty's total nearly quadrupled from a year earlier, to 4.11%. The company had said an ailing residential construction loan portfolio in California contributed to its loan problems.

Its ratio of loss allowances to noncurrent loans fell to 48.57% at yearend, from 68.7% at the end of 2007. "They have got a reasonable level of reserves, but they have a lot of nonperforming assets, too," Anderson said.

In the last three quarters of last year, Guaranty's mortgage-backed securities portfolio shrank 29%, to $3.5 billion at yearend, at least in part because of the declining value of the securities. According to its call report, it had $370 million of unrealized losses in its available-for-sale securities portfolio at yearend. "Obviously, they made some big missteps and bought mortgage-backed securities at the wrong time," Anderson said.

Brett Rabatin, an analyst at Sterne, Agee & Leach Inc., does not cover Guaranty's stock, but he said that many thrift companies take more risks in their securities portfolios than their counterparts in commercial banking typically take.

"Thrifts in a lot of cases tend to look at securities not just as liquidity, but as secondary income," he said. "A lot of times the bond portfolio has a higher level of risk."

John Blaylock, an associate director with Sheshunoff & Co. Investment Banking, said overall chargeoffs have lowered the tangible common equity ratio of Guaranty's thrift to 3.83%. (Many investors are using such ratios to judge the health of financial institutions.)

"They charged off almost two-thirds of the equity that was put in" last summer, Blaylock said. "They will have to have some capital coming to that entity at some point." Considering the potential losses from the loan and securities portfolios this year and next, he said, Guaranty may need to raise as much as $300 million.

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