Former Rangers players and staff paid through an offshore trust have been told they have just weeks to approach HMRC over a settlement or face an even larger tax liability.
Last year, the Supreme Court upheld a Court of Session ruling that £47 million paid to Rangers employees between 2001-2010 from an Employee Benefit Trust (EBT) was taxable employment income.
Now beneficiaries of the EBT, many of whom were led to believe these were loans that would not have to be repaid, are being warned to seek "urgent advice".
The most high-profile names at risk are understood to be former captain Barry Ferguson, former manager - and current Scotland boss - Alex McLeish and former owner Sir David Murray.
Where HMRC is unable to recover the tax from the employer, it may attempt to transfer the liability for unpaid tax to its employees or former employees.
While they can still pursue the liquidators for a portion of what the company owed, more could be salvaged by pursuing the former employees, which could put many on the hook for hundreds of thousands, or even millions, of pounds.
Time appears to be running out for former staff and players to try to negotiate a deal, with further charges to be applied by HMRC if tax liabilities have not been settled by 5 April 2019. To do that, those in question will have to approach HMRC by 30 September this year to enter into an agreement.
HMRC is tightening the net on the use of EBTs and have been contacting individuals whom they believe have benefited from the use of an EBT in a similar way. Many of these will be contractors and can date back years.
The implications of the Rangers case is being felt far beyond the world of football.
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