The court-appointed trustee in the case of David Drumm has told a court in Boston that she found it hard to understand the kind of mistakes that had been made on his statements of financial affairs given his "familiarity with financial matters".
Kathleen Dwyer said the omissions relating to the transfer of cash and property to his wife had taken months to address.
Under cross-examination by Mr Drumm's lawyers, Ms Dwyer said "if you're an honest debtor and make an honest mistake, the mistake is discovered and you fix it, there is no oh we're working on it, we'll have it done by next month'".
This, she said, is what was going on in Mr Drumm's case.
She said "it was the kind of mistake that was hard to understand in the first place, given the debtor's familiarly with financial matters".
She told Mr Mack, counsel for Mr Drumm, that Mr Drumm was "an accountant, a businessman, a banker", someone "who wouldn't be making mistakes", adding "it was unusual".
At several points in her testimony today, Ms Dwyer said that she had repeatedly told Mr Drumm and his advisors to amend their statements of financial affairs to include the omitted asset transfers.
She said she couldn't "do his job for him", saying he was a "sophisticated debtor with good counsel".
She said the system didn't work in a fashion where a trustee had to spot mistakes and give warnings.
She spoke of the efforts she went to trying to get information from Mr Drumm, and for him to swear to that information under oath.
She said that given Mr Drumm's background and the amount of money involved, it was not a kind of "mere oversight situation".
Ms Dwyer told the court that it was a situation whereby it appeared Mr Drumm was trying to wear her out and get tired of all the creditors' meetings. She said this was a common occurrence.
She said it struck her as "very unusual" that the statements of financial affairs had not been done correctly the first time, or the second or the third time. She said it was "very unusual" that transfers of $1m would be overlooked.
Mr Mack, for Mr Drumm, challenged her in terms of the fraud allegations that she was claiming against Mr Drumm.
The lawyer who completed Mr Drumm's original bankruptcy filings has said that she thought the paperwork had all been completed correctly.
Heather Zelevinsky was testifying at the bankruptcy trial of the former Anglo Irish Bank CEO in Boston today.
Ms Zelevinsky told the court that she never believed Mr Drumm was trying to conceal transfers of his assets.
that although she had qualified as a lawyer in 2005, she had only joined the firm Looney and Grossman, representing Mr Drumm, in June 2010, just a couple of months before working on his case.
She said she got involved in Mr Drumm's case in August 2010, when she and a colleague were working to prepare a personal financial statement for him in relation to litigation he was facing in Ireland.
She said she had worked on a lot of bankruptcy cases previously.
She said she found out in September 2010, before filing Mr Drumm's bankruptcy papers that he had transferred significant sums of money to his wife in the previous two years.
She said at the time, she thought she had filled out all the paperwork correctly. She said she did not believe the cash transfers needed to be included in the section she later learned they should have been.
Ms Zelevinsky said Mr Drumm never dragged his feet getting documents to her and never refused to answer questions.
She said that he was "very organised".
Cross-examination of Ms Zelevinksy will take place tomorrow morning.
After that, another of David Drumm's previous legal advisors will take the stand.
The final witness will be Mr Drumm's wife Lorraine, who is expected to take the stand tomorrow afternoon.
Earlier, Ms Dwyer told a court in Boston that she believes IBRC - formerly Anglo Irish Bank - owes Mr Drumm money.
Ms Dwyer is suing the bank for $3.68 million in unpaid compensation due to Mr Drumm.
She said she was challenging Mr Drumm's bankruptcy application because he had not fully disclosed his assets and transfers, and that this had impeded her efforts to distribute his estate to those he owes a combined $10.5m to.
However, under intense cross-examination, she admitted that she felt Mr Drumm was owed at least part of the $3.68m in unpaid compensation from Anglo Irish Bank.
Ms Dwyer was appointed as bankruptcy trustee to Mr Drumm's case, the day after he applied to have his debts discharged.
But Anglo Irish Bank - as it was then - challenged her appointment and a subsequent election voted for another attorney Michael Epstein to take over.
Ms Dwyer then filed a lawsuit outlining why Anglo Irish Bank was not entitled to vote on her appointment, citing a number of reasons, including the fact that the bank still owed Mr Drumm $3.68m.
This comprises $1.6m in unpaid salary, $1m in unpaid pension contributions and $62,000 in employee expenses, along with his 2006 bonus of over $900,000.
Ultimately the bank did not continue with its efforts to replace her as trustee and she went on to hire the bank's choice of trustee as an advisor on forensic financial matters.
But this lawsuit is still active, and when questioned by Mr Drumm's lawyers today as to whether she thought he had a claim to the money, she said that she believed that Mr Drumm is still owed money from the bank.
A decision on this lawsuit is due next week.
When questioned by Mr Drumm's lawyers about specific allegations of fraud that she had made against him, Ms Dwyer said that she could not recall why she had claimed it was fraud.
She insisted that she had made Mr Drumm and his lawyers aware at an early stage that they needed to refile their financial statements to include the cash transfers of over $1m made to his wife.
The court has previously heard from Mr Drumm's lawyers that they did not know about their failure to include the transfers until April 2011.
Ms Dwyer says she told them repeatedly up until and including 24 January 2011.