The private chauffeur who was sentenced to nearly five years in federal prison for stealing $34 million from Oregon-based publisher Win McCormack is making his third bid for early release — this time pointing to a commercial driver’s license he recently earned behind bars.
In early August, Sergey Lebedenko became one of the first four inmates at the federal prison in Sheridan to receive a commercial driver’s license through a special program coordinated with Chemeketa Community College. Inmates in the program are given furloughs to complete driver training in Salem.
A commercial driver’s license allows a person to drive buses and large trucks, and it can allow a driver to transport hazardous materials.
Lebedenko, 56, filed a court motion from prison, saying his confinement since March 2025 has been “mentally and physically difficult.” He expressed remorse, pledged never to reoffend and vowed to liquidate his assets to pay millions of dollars in restitution. He said he wants to turn the page as a “re-invented, law-abiding citizen.”
Lebedenko and his wife carried out what prosecutors called the largest theft against a single individual in Oregon federal court history. While working as McCormack’s chauffeur, Lebedenko exploited the publisher’s trust and made thousands of unauthorized charges on McCormack’s American Express card — nearly every day from 2017 through 2023 — to fund an extravagant lifestyle.
The couple used the stolen money to purchase 14 properties across Oregon, Washington and California that were worth more than $8.6 million combined. The properties included a $2.1 million home in Bermuda Dunes, California; a $1.1 million home in Battle Ground, Washington; and several houses in the greater Portland area, including residences for their two adult daughters and their pastor.
The court had ordered forfeiture of the assets the Lebedenkos purchased with proceeds of their fraud, including the properties and 19 financial accounts. As of earlier this year, the government reported it had recovered more than $4.5 million from the Lebedenko couple.
Lebedenko asked the court to cut nine months off his 57-month sentence, reducing it to a total term of 46 months, or three years and 10 months. He sought credit for the year and two months he spent on home detention before sentencing.
He argued that keeping him locked up longer would only delay his ability to make “financial amends,” and that early transfer to a federal halfway house would let him “re-enter society and become employed.”
He cited his clean record in custody, noting that he and three fellow inmates were the first at Sheridan permitted to leave the facility for community-based driver training. He said he pursued the license to “re-invent himself” with a “new high-paid profession,” and stressed that he is a first-time, non-violent offender.
Federal prosecutors were unmoved.
Assistant U.S. Attorney Sarah Barr noted this is Lebedenko’s third motion for early release — a judge denied both previous requests. She also pointed out that Lebedenko’s 57-month sentence was already at the low end of the guideline range of 57 to 71 months.
This time, Lebedenko also cited Amendment 838 to the U.S. Sentencing Guidelines to support his request. The amendment, which took effect Nov. 1, revises the associated penalties for sentencing in economic crimes by adjusting for inflation the amounts of money stolen. It should reduce his sentence by close to a year, he argued.
But Barr countered that the amendment was not made retroactive, making it an invalid basis for a sentence reduction for Lebedenko.
U.S. District Judge Amy Baggio has not yet ruled on the latest request.
Lebedenko, 56, who was convicted of conspiracy to commit wire fraud, wire fraud, and conspiracy to commit money laundering, has a projected prison release date of July 5, 2028. His wife, Galina Lebedenko, 51, who faced the same sentence of four years and nine months, is being held at the federal prison in Victorville, California, with a projected release date of July 4, 2028.
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