Bill Gross and PIMCO made a couple bets too many on the concept of “Too Big To Fail”. While scoring big on a bet on Fannie and Freddie, Gross gave it back and just a bit more with bets on Lehman (LEH), and AIG. The PIMCO Total Return Falls the Most in Three Years.

Bill Gross’s Pimco Total Return Fund, the world’s largest bond fund, fell 1.4 percent yesterday, the biggest one-day decline in more than three years, according to data compiled by Bloomberg.

The loss, which compared with the 0.38 percent drop by the benchmark Lehman Brothers Aggregate Bond Index, came as the U.S. government moved to seize American International Group Inc., the largest U.S. insurer. The fund guaranteed $760 million of AIG debt as of June 30, part of a larger bet by Gross that some beaten-down corporate bonds will recover because they are too important for the government to let fail.

Gross’s fund has fallen 2.3 percent since Sept. 8, reducing the gain this year to 2.8 percent. It ranks ahead of 92 percent of similarly managed funds, Bloomberg data show.

Gross, 64, Pimco’s co-chief investment officer, has made successful bets on mortgage-backed securities, Morningstar’s Jones said. About 65 percent of the fund’s holdings were mortgage-backed securities on June 30.

Gross also favored bonds of corporations that were “under the Fed umbrella,” meaning they were so big or important to the U.S. or global financial markets that the government couldn’t allow them to fail, Jones said.

The bankruptcy of Lehman (LEH) and the handling of AIG shows a deceasing willingness of the Fed to assume full responsibility for moral hazard bets as the Fed did with Fannie Mae (FNM) and Freddie Mac (FRE).

Those betting on “Too Big To Fail” better think twice. It appears the Fed’s balance sheet is becoming stuffed to the gills and it is reluctant to take on too much more risk, too quickly.

Pretty soon, the ability of the Fed to inflate will come into question, printing or not.

Mike “Mish” Shedlock
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