Jeffrey Levitt, once a high-rolling deal maker with airplanes, Rolls-Royces and lavish homes at his disposal, was handcuffed and led to prison this morning, stripped of all the possessions he brought with him except a change of underwear.

After a brief appearance in Baltimore City Circuit Court, Levitt, flanked by about a dozen burly sherrif's deputies, was led through a horde of jostling cameramen outside the courthouse and into a Corrections Department van that ferried him to the prison system's classification center in downtown Baltimore.

Levitt, 43, former president of Old Court Savings & Loan, the defunct thrift that triggered a crisis among the state's savings and loans last May, has been sentenced to 18 months in prison for violating a judge's order to limit his spending to $1,000 a week. Circuit Court Judge Joseph H.H. Kaplan issued that order at the request of the state, which filed a civil suit in an effort to recover $200 million for Old Court depositors from Levitt and other former officers of the thrift.

Levitt's wife Karol, who also was convicted of contempt of court, is to report to the women's detention center in the Baltimore City Jail Friday to begin serving her sentence of 15 weekends in jail.

Prison authorities said today that Jeffrey Levitt will be treated like any other inmate, although, at his request, he will be segregated from the general prison population.

Levitt is expected to spend six to eight weeks at the Reception, Diagnostic and Evaluation Center, a high-rise building across the street from the state penitentiary, before he is sent to an as yet undetermined prison facility. While at the center, he will be housed in a single cell, taking all his meals there and mixing with other segregated prisoners only for a one-hour recreation period each day.

At 9:30 a.m., before he was turned over to sheriff's deputies, Levitt appeared before Judge Edward J. Angeletti to enter a plea of not guilty to a 25-count criminal indictment charging him with theft and misappropriation of $14.6 million in funds from Old Court and another thrift institution.

Seats in the cavernous fourth-floor courtroom were filled with persons there to enter pleas on misdemeanor charges, many of whom looked on with curiosity. Levitt, dressed casually in a bright green sweater, brown corduroy slacks and deck shoes, appeared relaxed and smiled occasionally during whispered conversations with his two attorneys.

Angeletti scheduled a jury trial for June 2 on the criminal charges. The judge also said that lawyers for both sides have agreed, at his request, not to make any public statements about the case.

As the proceeding ended, a deputy approached with handcuffs and Levitt, appearing surprised, asked whether they were necessary. He was told that they were. After a brief conference with his lawyers in the judge's chambers, Levitt, trailed by an entourage of reporters, was taken aboard a freight elevator for a trip to the first-floor sheriff's lockup, where he was patted down and fingerprinted.

Deputies also went through a large green plastic trash bag that Levitt sought to bring with him to the jail, which they said contained towels, underwear, clothing, cologne, shaving items and two thick paperback books. He was allowed to bring the items to the prison reception center, but officials there confiscated everything but the underwear.

Once at the reception center, Levitt was strip-searched, sprayed for lice and given a physical. He traded the casual clothing he was wearing for prison-issue blue jeans, sneakers and a gray sweatshirt. His first lunch behind bars consisted of cabbage, cold cuts and pudding. Beef stew, noodles and an apple were on tonight's dinner menu.

Beverly Marable, a spokeswoman for the Corrections Department, said that Levitt would be occupying a 60-square-foot cell on a segregated "pod" or tier. Marable said that Levitt had asked to be separated from the general population because he had "concern about some threats he had received on the outside."

He will be locked in his cell for 23 hours a day, and allowed to mingle with other prisoners and watch television in a common area during a one-hour recreation period daily. A prison librarian takes requests for reading material several times a week, Marable said.

Today's events represent a long fall from grace for Jeffrey Levitt. Until last May, he was a high-flying financier who, along with other owners and officers of Old Court, put together scores of multimillion-dollar development deals.

The Levitts were a high-profile couple in Baltimore and Ocean City, where they own a beachfront town house. They gave generously to charities, vacationed in their $435,000 Florida home, and dined in Baltimore's finest restaurants as often as four or five nights a week.

Phillip Dantes, chairman of the state's parole commission, said today that he is uncertain whether Levitt will have to serve his entire 18-month term.

Dantes said that he has asked the state attorney general's office for an opinion on whether criminal contempt is an offense that can receive a parole. If so, Dantes said, Levitt would be eligible for parole in mid-June.