Bertelsmann has been ordered to pay $260.8m to two internet businessmen in a breach of contract lawsuit in the US.
The case centred on music giant's web ventures
Jan Buettner and Andreas von Blottnitz took action against the music giant over the creation and sale AOL Europe.
The two helped put together the music firm's 1995 merger with the web portal, but Bertelsmann later sold half its stake in AOL Europe for $6.7bn.
They said they were entitled to a slice of the proceeds when Bertelsmann sold its holding to Time Warner.
The payout decision comes more than a month after the pair won their case at a Californian court and a jury said the two should be awarded up to $1bn.
The jury found against Germany's Bertelsmann and in favour of each of the two men on four counts, awarding $250m on each count.
But lawyers for the two entrepreneurs accepted that the jury's intentions about the scale of the total payment and how it should be divided were unclear and required the judge's decision.
Judge James Brown then had to decide the full scale of the award for the pair.
In his ruling, Judge Brown also tacked on 4% in interest from the date the lawsuit was filed three years ago, which added $31m to the judgment - bringing the total pay-out to $292m.
However, he cleared Bertelsmann's former chairman and chief executive Thomas Middelhoff of personal liability in the case, saying the $40m jury award against him had been wrongly awarded.
Although Mr Buettner and Mr Blottnitz had asked the jury for $3.5bn, their lawyer Bill Price said his clients were "ecstatic" about the decision.
Mr Price added: "They think it's fair and just."
Following the news, Bertelsmann's lawyer attorney Anthony Murray said he planned to file motions asking the judge to either overrule the jury and find in favour of the company or grant a new trial.
If those motions fail, he said the company would appeal.