A Delaware judge has ordered the CEO of Dole Food Co. and his former right-hand man to pay $148 million in damages for misleading directors and shareholders in a deal that took the company private in 2013.

The judge on Thursday said David Murdock and former Dole chief operating officer and general counsel C. Michael Carter breached their fiduciary duties of loyalty in structuring a $1.2 billion cash buyout that left the company in Murdock's hands.

The judge said the 92-year-old Murdock and Carter deliberately took steps to drive down the stock price and understate the value of the food conglomerate.

A Dole Food spokeswoman said the company had no comment on the ruling.

Lawyers for Murdock and Carter did not immediately respond to email messages seeking comment.