Almost a decade ago, he signed away a multimillion-dollar coal licence to a union mate at a lavish dinner featuring suckling pig and a magnum of wine.
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On Thursday, former NSW Labor minister Ian Macdonald was found guilty of criminal misconduct over the deal and faces the prospect of joining his one-time political ally Eddie Obeid in jail.
A jury of 12 men and women took just under four days to find Macdonald guilty of two counts of wilful misconduct in public office.
Macdonald's political associate, former Construction, Forestry, Mining and Energy Union boss John Maitland, was found guilty of being an accessory before the fact.
It is second major trial resulting from historic inquiries by the Independent Commission Against Corruption into the activities of the former NSW Labor government.
The two men will remain on bail until they are sentenced by Supreme Court Justice Christine Adamson.
"Lock him up and throw away the key," Labor Opposition leader Luke Foley said after the verdict was delivered.
Obeid was jailed in December for a maximum of five years over his family's secret business dealings at Circular Quay. He has lodged an appeal against his conviction.
Obeid and Macdonald have also been charged over an alleged coal deal relating to an Obeid family property.
The Supreme Court heard Macdonald awarded a coal exploration licence to Doyles Creek Mining, a company chaired by Maitland, to cultivate the "friendship and loyalty" of the former union boss.
NSW Labor Opposition Leader Luke Foley gave evidence that Maitland supported Macdonald's bid for preselection for a seat in the upper house in 2007 at a time when others, including Mr Foley, were urging him to quit politics.
The jury was told unexplored coal resources were "as rare as hen's teeth" in NSW and the state was facing "budget constraints" when the multimillion-dollar licence was given away without a competitive tender in December 2008.
A BHP subsidiary paid $91 million in 2006 to explore for coal at Caroona in NSW while China Shenhua Energy Ltd paid $276 million in 2008 for its Watermark licence.
The court heard Doyles Creek Mining made no such payment.
The ICAC heard the men signed off on the deal at the upmarket Catalina restaurant in Rose Bay over an $1800 dinner.
Maitland made $6 million selling shares in a company that acquired Doyles Creek Mining after the licence was granted.
Macdonald had insisted he acted in the interests of the state and the Doyles Creek proposal included a plan for a training mine in addition to a commercial mining operation.
The two men also told the court they were not friends and had only a professional working relationship.
But Mr McHugh said Macdonald "misused his power" by placing the interests of a company chaired by his "mate" above the interests of the state.
Macdonald is now facing the prospect of a second criminal trial.
The former mining minister is accused of striking a deal to create a lucrative coal tenement over the Obeid family's rural property, Cherrydale Park.
The ICAC heard the decision made the Obeids $30 million with the prospect of millions more.
Macdonald and Obeid, along with Obeid's middle son Moses, will face a committal hearing in August to test the strength of the prosecution's case and determine if they should stand trial.
