So-called investment guru and market-maker Frank Quattrone faces sentencing tomorrow. An incriminating email nailed the banker, one of the most prominent Wall Street figures to grace a courtroom since Michael Milken fourteen years ago.

When he is sentenced in federal court in Lower Manhattan tomorrow, Frank P. Quattrone, the investment banker whose deal making helped fuel the 1990’s technology boom, will learn the penalty for pressing the “send” button on a one-line e-mail message urging his colleagues to “clean up those files.”

Mr. Quattrone, 48, who was found guilty in May on obstruction of justice after investigators began looking into his former employer, Credit Suisse First Boston, is the most prominent Wall Street figure to face prison since Michael R. Milken received a 10-year sentence in 1990.

The verdict against Mr. Quattrone, which he is appealing, came in a retrial after his first trial ended in a hung jury last fall. The jury in the second trial found that he did try to hamper criminal and regulatory investigations into the way that First Boston doled out hot stock offerings.

According to federal sentencing guidelines, Mr. Quattrone could be sent to prison for 10 months to 16 months. But the judge could decide that Mr. Quattrone, like Martha Stewart, who was also convicted of obstruction, can serve part of the sentence at home. Ms. Stewart was sentenced to five months in prison and five months of home confinement, which ran toward the more lenient end of the options that the judge in the Stewart case considered.

Mr. Quattrone’s sentence could be much more severe; prosecutors are expected to argue that he perjured himself when he took the stand in his own defense during the first trial.

If the judge in the case, Richard Owen, in United States District Court in Manhattan, agrees with that line of argument, Mr. Quattrone could face 15 months to 21 months, or more. Judge Owen, an appointee of President Richard M. Nixon who has a long of history of favoring prosecutors and whose own behavior and rulings during the trial is the basis for Mr. Quattrone’s appeal, once sent a financier to jail on contempt charges during a pretrial hearing in 1999. The financier, Martin Armstrong, who was accused of swindling Japanese investors, is still in prison on the contempt charges.

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