Media firm Hollinger is reported to have paid former chief Conrad Black and other senior executives $3m (£1.62m) in bonuses via an offshore bank.
The UK's Daily Telegraph is Hollinger's flagship publication
The money was wired to the Caribbean unit of a Canadian bank in December 2000, according to the New York Times.
The claim comes amid an official investigation into reports that Lord Black and other executives received unauthorised payments worth $32.2m.
Those revelations led Lord Black to quit as chief executive in November.
The bonuses were paid in December 2000 by Hollinger Digital, an offshoot of Hollinger, after the company had completed an offering in one business while selling off another.
Tax experts said that while the complex routing of the transactions was unusual, there did not appear to be anything illegal about the bonus payments.
And all of Hollinger's bonus payments for 2000, including a $1.8m (£1m) payment to Lord Black, were reported in its ffilings to the US stock market regulator.
However, the company - which owns a string of high-profile newspapers including the Telegraph titles in the UK - failed to disclose that some money had come from the operating unit.
Late last year, an internal investigation at Hollinger revealed that Lord Black and other
top executives pocketed payments worth £32.2m without the approval of the firm's audit committee.
The cash came from 'non-competition' fees paid by buyers of Hollinger titles in return for undertakings that the firm would not launch new rival products.
This angered shareholders, who argued that the money should have been ploughed back into the company.
Lord Black and other executives involved have agree to repay the money in full, with interest, by June next year.
Hollinger is considering selling off the Telegraph titles in an effort to shore up its finances, with several potential buyers thought to be lining up bids.