In exchange for the bribes, Simpkins, 61, of Haymarket, Va., steered multi-million-dollar Navy business deals to Leonard Glenn Francis, a Singapore-based contractor known as “Fat Leonard,” according to court records. Francis’s company, Glenn Defense Marine Asia, held contracts for more than 25 years to resupply and refuel Navy ships and submarines at ports across Asia.

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Court records show that Simpkins and Francis met in a Singapore hotel bar in 2006 to discuss how to rig the awarding of lucrative contracts to service Navy vessels in Thailand. Prosecutors have said Francis first gave the Navy official an envelope stuffed with $50,000 in cash. In subsequent months, according to the plea agreement in the case, Francis wired another $300,000 in bribes to a Japanese bank account controlled by Simpkins’ wife.

Prosecutors say that Simpkins received more money in bribes than any other Navy official charged in the scandal. “Simpkins valued and sold his office to Francis in the same manner as an automobile dealer sells used cars,” they wrote in a court filing.

Besides steering contracts to Glenn Defense, Simpkins acted as a secret enforcer of the company’s interests. According to the plea agreement, he ordered other Navy officials to stop reviewing fraudulent invoices from the firm, and blocked the installation of special equipment that would have detected a scheme by Francis to overcharge the Navy for pumping wastewater from its ships. On another occasion, he overruled a recommendation from a junior officer to cancel one of Glenn Defense’s contracts for poor performance.

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Simpkins also had a fondness for prostitutes that Francis exploited, court records show. After his retirement from the Navy, Simpkins returned to Singapore for a visit in 2012 and emailed the contractor with a request for “some clean, disease-free wome[n].” Francis replied that he would arrange for prostitutes, referring to them as “honeys and bunnys.”

In a letter sent to the court for his sentencing, Simpkins said he took “total responsibility and accountability for my actions and offer no excuse[s]. There are not enough words to accurately and sincerely express my apology to the United States and my family.” He did not make any reference to Francis — who has also pleaded guilty and is in jail awaiting sentencing — or shed any more light on their actions.

“Mr. Simpkins is sincerely remorseful and looks forward to putting this chapter of his life behind him,” his attorney, John Lemon of San Diego, said in an email.