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  1. People

Robert Pleines, Jr.

Senior Managing Associate
Cleveland
T.
216.363.4491
liamE

Bob represents a variety of commercial shippers, motor carriers, freight brokers, manufacturers, and distributors with regulatory compliance counseling, contract and policy drafting, and business consultation. He has experience advising clients in several transportation modes, including truckload, less-than-truckload (LTL), and refrigerated, and regularly provides strategic legal and operational guidance to clients who engage independent contractor owner-operators.

Bob works closely with a number of last-mile freight delivery providers and freight brokers to develop compliant transportation models that meet the demands of modern deliveries while adhering to federal and state transportation regulations. He regularly counsels clients on contract design and compliance procedures that minimize risk and enhance operational efficiency.

He is also well-versed in a variety of transportation-related rules regulations, including the Federal Leasing Regulations (FLRs), Federal Motor Carrier Safety Regulations, (FMCSRs), regulations set forth by the California Air Resources Board (CARB), and the Federal Motor Vehicle Safety Standards (FMVSS). He has previous experience as a litigator at a regional insurance defense firm where he represented commercial motor carriers and their drivers in complex pre-suit claims and lawsuits involving wrongful death, personal injury, cargo, and property damage.

Outside of his practice, Bob is a Major in the United States Marine Corps Reserve and currently serves as a Detachment Officer-in-Charge. He is a commissioned officer with over a decade of experience in collaborative project development and leadership-driven unit cohesion.

Representative Experience

  • Representation of numerous carriers, brokers, and shippers in contractual drafting and negotiations.

  • Offered specialized counsel and tactical guidance to clients transitioning between transportation service providers, ensuring seamless operational shifts and regulatory compliance.

  • Reviewed and offered strategic guidance on multiple owner-operator models, ensuring compliance with the Federal Leasing Regulations and acceptable industry practice.

  • Developed ground transportation models and crafted template agreements to support these new models, ensuring legal compliance and operational efficiency.

  • Advised freight brokers and motor carriers in the last-mile delivery space as to applicable permitting and licensure requirements.

  • Drafted, reviewed, and provided comprehensive counsel on multiple dedicated motor carrier services agreements, tailoring solutions to meet shippers’ specific transportation needs.

  • Litigation
  • Transportation & Logistics
  • International Trade & Supply Chain Management
  • Cleveland State University College of Law, 2016, Juris Doctor
    • Cleveland State Law Review, Associate of the Year (2013-2014)
    • Managing Editor of the Year (2015-2016)
  • Ohio University, 2012, Bachelor of Arts
    • magna cum laude
    • Randolph Stone Award Winner, History Essay Competition, 2012
    • Political Science Outstanding Intern Award, 2012
    • Publication: “The New Deal’s Impact on American Socialism,” Ohio University Undergraduate Journal of History
  • Ohio
  • Listed, Ohio Super Lawyers - Rising Stars, 2024-2025
  • Member, Ohio State Bar Association
  • Member, Cleveland Metropolitan Bar Association

Highlights

Articles and Presentations
October 16, 2025
Delivery Network Carrier Models and the Evolution of Last-Mile Residential Delivery
September 3, 2025
Jonathan R. Todd, Brian Cullen, and Robert Pleines, Jr. Publish Article in Star Carrier | New Emissions Environment & You
July 24, 2025
Marc S. Blubaugh, Vanessa I. Gomez, Robert Pleines, Jr., and Jonathan R. Todd publish article in Star Carrier | English Language Enforcement - Changes coming to FMCSA rules for truck drivers

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News
July 8, 2025
Benesch Client Bulletin Tops Mondaq Readership Rankings | "Government Contracting Under the Trump 47 Administration"
December 17, 2024
49 Benesch Attorneys Selected to 2025 Ohio Super Lawyers and Rising Stars
July 25, 2024
Benesch Managing Associate Bob Pleines Promoted to Major in U.S. Marine Corps Reserve

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