The billionaire chief executive of Dole Food Co. and his top lieutenant must pay $148.2 million of damages to shareholders they shortchanged when the produce company went private in 2013, a Delaware judge ruled on Thursday.

In a decision that may cast a pall on management-led buyouts, Vice Chancellor Travis Laster said Dole Chief Executive David Murdock, 92, and former Chief Operating Officer C. Michael Carter were liable for depressing the stock so that Murdock, who owned 40 percent of Dole, could buy the rest at a lowball price.

The judge said the $1.2 billion buyout undervalued Dole by 17 percent, letting Murdock pay $13.50 per share rather than the $16.24 that Dole was worth.

Deutsche Bank AG, which advised Murdock on the buyout, was cleared of liability because it did not knowingly participate in wrongdoing. Murdock is worth $3.4 billion, Forbes magazine said.

Thursday’s award is among the largest in a class action lawsuit alleging that a company sold itself for too low a price, and highlights conflicts that managers wanting to buy their own companies may face in wanting to keep costs down.

“It will make it harder to do management buyouts, and it should be,” said Charles Elson, a governance specialist at the University of Delaware. “The inherent conflicts are almost impossible to resolve. The ruling sends a signal that Delaware courts will be suspicious of these sorts of transactions.”

More than half of U.S. publicly-traded companies are incorporated in Delaware, whose courts hear many valuation-based challenges to takeover bids.

Judge Finds Fraud

Shareholders accused Murdock and Carter of driving down Dole’s share price by downplaying the Westlake Village, California-based company’s ability to boost profit by cutting costs and buying farms, and canceling a stock buyback.

In his 106-page decision, Laster saw Carter as the main engineer of the scheme, calling him Murdock’s “right-hand man” and saying Carter “actually engaged” in fraud.

“Although facially large, the award is conservative to what the evidence could support,” Laster wrote.

A nine-day trial was held in February. Several hedge funds had asked Laster to appraise Dole’s value, but the judge said that issue may be moot.

Dole declined immediate comment on behalf of the itself, Murdock and Carter. Deutsche Bank spokeswoman Renee Calabro declined to comment.

Objecting shareholders had sought higher damages, but their lawyer Stuart Grant called the decision a “decisive” victory.

“It wakes insiders and investment banks on their proper roles in a management-led buyout, and shows that management can’t dictate the terms and the flow of information,” Grant said in an interview. “It shouldn’t be a Wild West.”

Not A “Confused Old Man”

A high school dropout who made much of his fortune in real estate, Murdock was Dole’s chief executive from 1985 to 2007, and again starting in 2013.

He had taken Dole private in 2003 and sold 60 percent in a 2009 initial public offering, in part to pay down debt as the U.S. economy struggled.

Murdock said he hoped through the latest buyout to combine Dole with his North Carolina research center, which seeks to unlock secrets of health and longevity.

But shareholders called the move a power play. Laster appeared to agree, calling Murdock “an old-school, my-way-or-the-highway controller, fixated on his authority and the power and privileges that came with it.”

The judge said Murdock hurt himself during trial testimony, where defense counsel portrayed him as both a “confused old man” and a disengaged CEO.

“By dint of his prodigious wealth and power, he has grown accustomed to deference and fallen into the habit of characterizing events however he wants,” Laster wrote.

“That habit serves a witness poorly when he faces a skilled cross-examiner who has contrary documents and testimony,” he added.

The cases are In re: Dole Food Co. Inc. Stockholder Litigation and In re: Appraisal of Dole Food Co. Inc., Delaware Chancery Court, Nos. 8703, 9079.

(Reporting by Jonathan Stempel in New York; Editing by Alden Bentley and Christian Plumb)