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Former Trucking Company Operator Given 3 Years in Prison

Dragan Simovski, the operator of Illinois-based Freedom Transportation was sentenced to 3 years in prison for his connection to an illegal double-brokering scheme.

by Staff
May 15, 2015
Former Trucking Company Operator Given 3 Years in Prison

 

1 min to read


Dragan Simovski, the operator of Illinois-based Freedom Transportation was sentenced to 3 years in prison for his connection to an illegal double-brokering scheme. He was also ordered to pay $532,000 in restitution.

Simovski pleaded guilty in December of last year to wire fraud in connection with the scheme. He admitted that he and other individuals were involved in a fraudulent double-brokering scheme by falsely representing that Freedom would use its own trucks to transport freight, knowing that Freedom had no trucks.

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Simovski entered into contracts with companies on behalf of Freedom promising to transport the freight and used information on the freight to find other companies to transport and deliver it.  Freedom would bill the customers for the jobs with Simovski and a co-conspiring broker pocketing the money.

The companies that actually carried out the work were never paid costing them approximately $532,000 in losses.

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