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When Conrad Black sold his New York apartment last year for $10.5-million (U.S.), it looked like a straightforward real estate deal. But the sale has been far from ordinary, having been caught up in a series of legal battles that have become ever more complicated.

The co-op apartment is not only enmeshed in the criminal proceedings involving Lord Black and several other former executives of Hollinger International Inc., but Lord Black is also involved in a lawsuit with the agents who sold the property, Sotheby's International Realty Inc.

Sotheby's is demanding immediate payment of its $557,500 commission on the sale. But Lord Black is fighting back, alleging the company conspired with the FBI to have his proceeds seized. The money is now being held by prosecutors to help cover Lord Black's bail in the criminal case. He and the others have pleaded not guilty, and a trial is expected to start next March.

In a court filing two weeks ago, Lord Black said Sotheby's created its own problems and he accused the firm of oversimplifying the case.

"Sometimes, simpler is not better — or even accurate," Lord Black's lawyers said in the filing.

Ownership of the Park Avenue apartment has been controversial for a while.

At one time, both Lord Black and Chicago-based Hollinger, which he once controlled, owned units in the same building. Hollinger paid $3-million for a second-floor apartment in 1994, while Lord Black bought a smaller unit on the ground floor for $499,000 in 1998.

Prosecutors allege that, in 2000, Lord Black orchestrated a deal in which he acquired the Hollinger unit for a discount in return for his apartment. Lord Black has disputed that allegation and said the deal was legitimate and that he paid for substantial renovations to the Hollinger apartment.

In April, 2005, Lord Black signed a contract with Sotheby's to sell the apartment. It's not surprising he turned to Sotheby's since he once served as a director of the former parent company, Sotheby's Holdings Inc.

It was an attractive listing. According to court filings and other documents, the apartment featured four marble frescoes in the front hall, a 30-foot-long living room, a library and four wood-burning fireplaces.

On June 8, developer Martin Berman and his wife, Phyllis, agreed to buy the apartment. They put down a deposit and agreed to pay the remainder on Oct. 7. On that day, lawyers for all sides assembled at the office of the company that manages the building.

According to a filing by one of Lord Black's lawyers, Allison Hirsch, the closing "was strange and unusual." Lawyers for the Bermans handed over a cheque for the balance and then "scurried and quickly left the closing room" along with representatives from Sotheby's. Ms. Hirsch, who acted for Lord Black on the real estate deal, said in the filing that, as she headed for the elevator, FBI agents handed her a warrant and seized the money, about $8.9-million in total.

Ms. Hirsch alleged that, prior to the closing, the Bermans sought assurances from prosecutors that the government would not interfere with the couple's purchase of the apartment.

She alleged that that showed there was a secret plan to tip off the police and deprive Lord Black of the money. Lord Black was indicted in Chicago several weeks after the money was seized and the proceeds are being used to help cover his bail.

Sotheby's has sued Lord Black in New York for its commission. The firm alleges the commission has nothing to do with the criminal case and that Lord Black should pay the fee.

In his response, Lord Black said he planned to pay the commission and other taxes out of the proceeds of the sale, which is customary in real estate deals.

If the criminal charges against him are dropped, Lord Black argued, the money will be returned and he will be able to pay the fee. Until then, the money remains tied up, largely as a result of Sotheby's own actions, he alleged.