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If the prosecutors going after Conrad Black hoped to build their case around the testimony of former Hollinger Inc. executive Fred Creasey, they're in trouble.

Lawyers for Lord Black and his co-accused repeatedly tripped up Mr. Creasey on documents during cross-examination yesterday and tore apart his calculations for the cost of a trip Lord Black took to Bora Bora in 2001 on a Hollinger jet.

"One thing you managed to do is to charge Mr. Black for the most expensive flight to Bora Bora in the history of mankind," Edward Greenspan, Lord Black's lawyer, told Mr. Creasey after suggesting that Lord Black was overcharged more than $18,000 an hour for the flight.

Prosecutors are trying to convince the jury that Lord Black and three other former Hollinger executives took more than $80-million (U.S.) that belonged to company shareholders by misusing non-compete agreements and abusing company benefits such as the jet. Lawyers for Lord Black and the others -- John Boultbee, Peter Atkinson and Mark Kipnis -- have argued the payments were legal.

Mr. Creasey was a senior financial manager at Toronto-based Hollinger from 1988 until 2004, when he left the company for medical reasons.

During questioning on Wednesday by prosecutor Julie Ruder, Mr. Creasey told the jury that by late 2003 he had become concerned about payments related to the non-compete agreements. He testified that he told Lord Black and others that the company had not fully disclosed the arrangements to shareholders. He also said that when the issue was being investigated internally in the fall of 2003, he tried to verify whether the payments had been approved by the company's directors. "I was unable to find any approvals for the non-compete payments," he told the jury.

Yesterday, Mr. Creasey's testimony began to unravel almost from the moment Mr. Boultbee's lawyer, Patrick Tuite, began cross-examination for the defence.

Mr. Tuite showed Mr. Creasey a regulatory filing dated Nov. 16, 2000, that Hollinger filed with the Securities and Exchange Commission. He pointed out that Mr. Creasey signed the filing and that it outlined many of the non-compete payments. Mr. Creasey said he could not recall the document but he acknowledged, "I don't doubt that I signed it."

Mr. Tuite pulled out several more documents that had been sent to Mr. Creasey in 2001 and early 2002, which also spelled out the non-compete payments. Some noted that the payments had been approved by company directors. When asked repeatedly about the material, Mr. Creasey replied that he couldn't remember. At one point Mr. Tuite snapped that Mr. Creasey seemed to remember conversations in the 1990s when he was quizzed by Ms. Ruder but couldn't remember discussions in 2003 when Mr. Tuite asked.

Mr. Greenspan then took on Mr. Creasey about the flight to Bora Bora on a Hollinger jet. Prosecutors have alleged that the trip was a vacation for Lord Black and his wife, Barbara Amiel, and that shareholders picked up the tab.

On Wednesday, Mr. Creasey explained that part of his job involved allocating costs of the company's two jets, one used by Lord Black and the other by his former right-hand man David Radler, who has pleaded guilty.

He testified that the company spread the costs among various Hollinger entities and did not break out personal trips because the two men worked all the time. He said the Bora Bora trip was exceptional because it was outside the company's normal operating area. He calculated the cost of the trip, which took 23.1 hours, at about $560,000. When he asked Lord Black how to allocate the cost, Lord Black offered to pay half personally. In the end, Hollinger-related companies covered the costs but a $565,000 taxable benefit was included on Lord Black's 2002 T4 statement as income.

Yesterday, Mr. Greenspan took Mr. Creasey's calculations to task. Mr. Creasey had based his costs on the trip going from Seattle to Bora Bora and back. That was because at the time Hollinger covered all jet costs for trips within the United States, Canada and Europe. Bora Bora was outside those areas.

Mr. Greenspan pointed out that the Blacks had stopped in Hawaii en route to Bora Bora. "You and I are Canadians," Mr. Greenspan said to Mr. Creasey, "but we know that Honolulu is in the United States." The Seattle to Hawaii leg cut 10.8 hours off of Mr. Creasey's 23.1-hour calculation, he added.

He also said that Mr. Creasey had rounded up his cost estimate when he calculated the amount of taxable benefit charged to Lord Black. "That's something that H&R Block would never do: round it up and make the taxes more," Mr. Greenspan said. "Who got charged for the rounding up? Mr. Black, right?"

Mr. Greenspan said the company should have applied a fair-market value for the taxable benefit, roughly $6,000 a hour, but Mr. Creasey charged $24,000 a hour.

Under repeated questioning by Mr. Greenspan about his knowledge of tax rules, Mr. Creasey had to acknowledge that he was not familiar with tax rules.

Prosecutors won't likely get another chance to question Mr. Creasey in front of the jury until Monday afternoon. But before then, Mr. Creasey will be cross-examined by two more defence lawyers.