Former V/Line chief executive James Pinder was jailed for two years and eight months with a non-parole period of one year and nine months for misconduct of public office in the Victorian County Court on Thursday.
Transclean co-director George Haritos was handed a term of two years and three months with a minimum of one year and five months for conspiracy to give secret commission and two counts of giving secret commissions.
The company's other co-director Alex Kyritsis and employees Steven Kyritsis and Maria Tsakopoulos were each given community corrections orders and ordered to do unpaid community service.
All five pleaded guilty to charges brought by the Victorian corruption watchdog following its Operation Esperance investigation into serious corrupt conduct in the state's V/Line and Metro's tendering and procurement processes.
The offending occurred between April 2018 to August 2020, when Pinder, as V/Line boss, participated in awarding a large-scale cleaning contract to Transclean worth more than $54 million.
Pinder, 58, had corruptly pocketed $330,000, including a $100,000 loan for the deposit on his Williamstown home, to further the interests of his friend's cleaning business.
The court was told Pinder met Haritos when they worked together at Metro. Tsakopoulos was in a relationship with Haritos and Alex was married to his sister and is the father of Steven.
When his application for a loan for settlement was rejected Tsakopoulos wired Pinder another $220,000.
Haritos was captured on a secret camera placing a bundle of cash totalling $10,000 in a white envelope into Pinder's car on another occasion.
Tskapolous had discussed with her lawyer and friend a false loan agreement to explain the sudden influx of funds to Pinder's bank account and whether to destroy an earlier, inconsistent version of the document.
The extent of Alex's involvement in the scheme revolved around him gathering $8000 at Haritos' direction to supply to Pinder as a secret commission.
His son Steven's involvement was not peripheral and included handing over sums of cash in envelopes to former Metro Trains boss Peter Bollas with Haritos, telling him he "earned it".
"It is is an evaluative remark unavailable to a person who did not know the extent of what the recipient had done," the judge said.
Bollas was sentenced in 2024 to a community corrections order after he helped Transclean pass audits on the company's work by sharing audit schedules ahead of time.
Judge Todd said the conduct was "corrosive of public trust" and had a "metastatic quality" leading honest contractors thinking they must behave in the way they did to secure work.
"Loss (in this case) is referable to the corruption of the trust that citizens of this state place in public servants, that taxpayer funds will be honestly expended in the public interest," she said.
Supporters of Haritos cried in court when his jail term was announced and Pinder, a permanent resident, faces the possibility of deportation to the United Kingdom upon his release.
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