Anglo Irish Bank chiefs tried to get Sean Quinn to sell his secret shares in the bank by putting pressure on his top manager, it was claimed in court.
Matt Moran, Anglo's former chief financial officer, said the businessman failed to stick with a plan to 'dribble' his stake on the market months before the bank lent money to its top customers money to buy them out.
A jury in the trial of three Anglo executives saw an email from Mr Moran describing a conversation with the Quinn Group's chief executive Liam McCaffrey.
"S***ted him up significantly and no doubting his own deep concern," Mr Moran wrote to his colleagues in May 2008.
The court heard the Financial Regulator was also putting pressure on Anglo as Quinn had only released 400,000 shares over two weeks, instead of an expected 800,000 a day.
"It was my understanding from conversations with Liam McCaffrey that Sean Quinn did not want to proceed with the sale," Mr Moran told the court.
Mr Moran, who has been granted immunity from prosecution, was giving evidence for a third day at the trial of Sean FitzPatrick (65), from Greystones, Co Wicklow; Patrick Whelan (51), of Malahide, Co Dublin; and William McAteer (63), of Rathgar in Dublin.
The men have pleaded not guilty to 16 charges of unlawfully providing financial assistance to individuals for the purpose of buying shares in Anglo Irish Bank in 2008.
Mr Whelan has also denied seven charges of being privy to the fraudulent alteration of a loan facility letter.
The court heard David Drumm, the former chief executive of Anglo who is not on trial, had raised the possibility of there being a "legal issue" under the 1963 Companies Act over lending money to buy its own shares four months before the Maple 10 deal.
"If we had the approval of the regulator would there be any legal issue (company law) with lending against our own shares," Mr Drumm wrote on March 19, 2008, to Mr Moran.
"As I understand it, we have an out under Section 60 if our loan is in the 'ordinary course of business'.
"In our case that means lending. Let's look at this option tomorrow."
The jury was shown a series of emails from March 2008 – when the bank was first trying to finalise an agreement to unwind Mr Quinn's near 30pc interest in the bank – and July when the deal was executed.
Mr Moran said he got an email from Mr Drumm on March 31 saying "he" wanted regulator references to be removed from the agreement between the bank and Mr Quinn.
"I believe he refers to Con Horan," Mr Moran said under cross-examination by Brendan Grehan, for Pat Whelan.
"So the regulator wanted references to the regulator removed?" Mr Grehan asked.
"That's my understanding," Mr Moran replied at the Circuit Criminal Court.
Mr Moran said the Financial Regulator had been told a short-term loan would be made available by the Quinn family to fund them buying the shares and that he would have expected the regulator to raise a flag if there was an issue.
Mr Moran also alleged that during discussions with the bank's solicitor, Robert Herron, in March 2008, Mr Herron said the regulator would raise no objection to the deal.
The former Anglo executive again outlined several initiatives the bank took to try to unwind the Quinn stake before its top 10 customers were approached in July 2008 to take part in a €450m deal.
The trial continues.