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.
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.

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.
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.
More Fleet Management

BeyondTrucks Targets Rate Complexity with New AI RateAgents
BeyondTrucks says its new RateAgents can turn plain-language rate logic into working code, starting with fuel surcharges — a critical but notoriously complex piece of carrier revenue.
Read More →
Volvo Sees Market ‘Tipping Point’ as New VNL Orders Surge
Soft freight conditions persist, but aging fleets, strong order intake, and new-product momentum signal a more optimistic second half of 2026, Volvo Trucks North America says.
Read More →
Cargo Theft’s New Playbook: Strategic Fraud, Double Brokering, and Cybercrime Hit Trucking
Cargo theft is evolving from regional smash-and-grab operations to sophisticated fraud schemes. Strategic theft now accounts for roughly a third of cargo crime, with incidents rising sharply in recent years. Here’s how the schemes work — and what fleets can do to protect themselves.
Read More →
HDT Honors the Best New Products of 2025 at TMC [Photos]
Heavy Duty Trucking's Top 20 Products awards recognize the best new products and technologies. Check out the award presentations at the 2026 Technology & Maintenance Council annual meeting.
Read More →
Detroit Engines: Trusted Performance, Built for What's Next
The Detroit® Gen 6 engine platform proves that real progress doesn’t require a complete redesign. Built on 20 years of trusted technology, these engines are designed for efficiency, stronger performance, and greater reliability than before. And they do it all while complying with 2027 EPA standards on every mile.
Read More →
Q&A: What's Real in Advanced Truck Tech? ACT Expo's Erik Neandross Weighs In
The 2026 ACT Expo is focusing heavily on what organizer Erik Neandross calls trucking's digital frontier. This interview excerpt dives into artificial intelligence, zero-emission vehicles, and tips to make sense of it all.
Read More →
Trucking's Digital Frontier: AI, Connected Vehicles, Alternative Fuels and More
There's an amazing amount of new technology for trucking out there. For fleets, the challenge is figuring out what’s real, what’s hype, and what’s worth investing in.
Read More →
What's Real in Advanced Truck Technology? ACT Expo's Erik Neandross Weighs In
Artificial intelligence, the software-defined vehicle, telematics, autonomous trucks, electric trucks and alternative fuels, and more in this HDT Talks Trucking interview
Read More →
ACT: Trucking Volumes Rise, Capacity Tightens as Fuel Prices Cloud Outlook
ACT Research data shows volumes hitting a four-year high and supply-demand balance strengthening, but higher oil prices are undercutting tariff relief and tempering optimism.
Read More →
Wabash Teams Physical Security With Digital Tech For Better Cargo Visibility
The patent-pending cargo solution integrates a digitally connected cargo door and an intelligent locking system with the TrailerHawk.AI technology platform.
Read More →
