A leading entertainment and media lawyer has been ordered to repay a loan of $540,000 to Barclays bank after he lost a landmark case relating to the collapsed US firm Dewey & LeBoeuf.

The dispute arose after Barclays sought to recover $56m in outstanding loans from 220 of the firm's partners, who had borrowed the money to fund their capital contributions, after Dewey & LeBoef filed for bankruptcy in 2012.

Partner Londell McMillan, whose clients included Michael Jackson and Stevie Wonder, disputed his obligation to repay the loan, claiming that as it was negotiated by the firm, he was not responsible.

But, in his ruling, the honourable Mr Justice Popplewell said he could not describe McMillan, who represented himself with the help of a McKenzie friend, as a careful and straightforward witness whose evidence could be treated as reliable.

'He was at times unwilling to accept what was plain on the face of documents and seemed to me to have convinced himself of a version of events which was inconsistent with the contemporaneous record. I do not feel able to rely on his evidence where it was in dispute and not supported by a document,’ the judgment said. 

During the trial McMillan had asserted that he had neither wanted nor needed to fund his capital account, saying the loan was used to provide working capital for the firm, which was in financial difficulties. He also said that he was ‘confused’ when signing the loan agreement and did not understand that it would be used to fund his capital contributions.

Ruling against him, Popplewell said this view was ‘untenable’ based on correspondence shown in court, and said that as an experienced and senior partner in a major international law firm, McMillan was not ‘a naïve or vulnerable consumer’.

He also pointed out that the terms of the loan were standard at the time for partner capital loan programmes and that McMillan was under no obligation to finance his capital contribution through a loan from Barclays.

The case had been listed to be heard with three other partners at the firm, Lester Charles Landgraf, Elias Farrah and Lewis Rosenbloom, but they all settled out of court.