Chicago Bootcamp
Thursday, January 22, 2026
Justin Olsen will be opening the Broker Bootcamp with a primer on the legal framework in which freight broker operates. He will lead a discussion on the statutes and federal regulations that define brokers, the requirements to be a broker, and the statutes and regulations that govern the business of freight brokers.
Moderator: Stevan Baxter, Skoubye Nielson & Johansen, LLC, Salt Lake City, Utah
Panelist: Justin Olsen, England Logistics, Inc., Salt Lake City, Utah
Every broker experiences cargo claims. Caroline Synakowski and Brittani Bushman will outline what cargo claims are, brokers’ exposure to liability by contract or by actions, federal statutes addressing broker liability, and the case law interpreting broker liability. This is a nuanced topic that will cover everything from business considerations for freight brokers to legal strategies in defending cargo claims, and up to date tips training brokerage employees to identify fraud indicators and out-maneuver would-be fraudsters.
Moderator: John F. Wilcox, Jr., Dysart Taylor McMonigle Brumitt & Wilcox, P.C., Kansas City, Missouri
Panelists: Brittani Bushman, Skoubye Nielson & Johansen, LLC, Salt Lake City, Utah
Caroline Synakowski, Associate Corporate Counsel, Flexport, Inc., Stanfield, North Carolina
Casualty claims present serious exposure problems for brokers. Matt Koch and Seth Howard will lead a panel on the FAAAA relationship to casualty claims, exceptions to broker protections, issues of vicarious liability, joint venture, and financial control. They will end with a discussion on negligent hiring and the Restatement of Torts section 411.
Moderator: John F. Wilcox, Jr., Dysart Taylor McMonigle Brumitt & Wilcox, P.C., Kansas City, Missouri
Panelists: Matt Koch, Marwedel, Minichello & Reeb, P.C., Chicago, Illinois
William S. Howard, Chartwell Law, Chicago, Illinois
Torrie N. Poplin, Of Counsel, Chartwell Law, Chicago, Illinois
Good contracts are the foundation of every successful brokerage. Rob Moseley and Matt Grimm will walk through shipper broker contracts, broker carrier contracts, co-broker contracts, and the insurance framework that every broker needs to understand when building their risk management program.
Moderator: Stevan Baxter, Skoubye Nielson & Johansen, LLC, Salt Lake City, Utah
Panelists: Rob Moseley, Moseley Marcinak Law Group, Greenville, South Carolina
Matt Grimm, Integrated Specialty Coverages, Tyler, Texas
The Broker Bootcamp will end with Arturo Rivera, Jaclyne Reive, and Jonathan Todd teaching a class on brokerage standards and procedures in Canada and Mexico and the relationship between brokers, shippers, and motor carriers in those jurisdictions. They will also provide important insights on cross-border brokerage and international freight forwarding.
Moderator: John F. Wilcox, Jr., Dysart Taylor McMonigle Brumitt & Wilcox, P.C., Kansas City, Missouri
Panelists: Arturo Rivera, Sesma, Sesma & McNeese, S.C., Mexico City, Mexico
Jaclyne Reive, Miller Thomson LLP, Toronto, Ontario, Canada
Jonathan Todd, Benesch, Friedlander, Coplan & Aronoff, LLP, Cleveland, Ohio
Presentation Slides (Jonathan Todd)
Chicago Regional Seminar
Friday, January 23, 2026
In today’s highly litigious business environment, effectively structuring your operations is crucial for safeguarding assets and minimizing risk. Join us for a comprehensive session that outlines strategic approaches to carve out services and assets, ensuring your most valuable resources remain protected while managing exposure in riskier segments. Our expert panel will discuss the advantages of creating distinct entities for various operational facets—such as separating warehousing as a parent entity from riskier asset-based and brokerage transportation services. Learn how proper structuring can impact insurance coverage and cost allocation while shielding the corporate veil, ultimately leading to a more resilient business model. We will also address the challenges involved in communicating these changes to leadership, sales teams, customers, and employees. Effective execution is key, and we’ll cover essential considerations like licensing requirements (FMCSA, NMFTA, UCR, and more), amending contracts with customers, carriers, and vendors, and aligning employee structures with IRS regulations and payroll considerations. Additionally, we’ll explore the importance of business alignment through technology systems, including Transportation Management Systems (TMS) and HR Information Systems (HRIS), to ensure smooth integration and ongoing operational success. Whether you’re contemplating a major restructuring or looking to optimize your current setup, this session will provide you with the tools and insights necessary for a successful transition.
Panelists: Jay B. Freeman, Vice President, Deputy General Counsel, CJ Logistics America, LLC, Des Plaines, IL
Jeffrey Simmons, Vice President, National Transportation Practice, McGriff, a Marsh & McLennan Agency LLC company, Phoenix, Arizona
Union Pacific and Norfolk Southern have announced plans to combine, but the consolidation is subject to approval by the Surface Transportation Board under an untested standard that the combination must enhance competition. One way in which UP and NS are making this case publicly is through greater competition with trucks. This panel will provide an explanation of the regulatory process ahead and potential impacts on the industry generally.
Moderator: Jameson Rice, Partner, Holland & Knight LLP, Jacksonville, FL and Washington, D.C.
Panelists: Greg E. Summy, Of Counsel, Woods Rogers Vandeventer Black PLC, Norfolk, VA
Bradon J. Smith, Attorney, Fletcher & Sippel LLC, Chicago, IL
The ‘America First Trade Policy’ under the Trump Administration has rapidly changed international trade practices in the supply chain. A panel of experts including private lawyers and an FMC Commissioner will address tariffs on imported merchandise, U.S. Supreme Court litigation over the constitutionality of those imposed tariffs, demurrage and detention billing practices by ocean cargo carriers, services contracts and anticompetitive agreements, and improving efficiency in the maritime and intermodal supply chain.
Panelists: Daniel Maffei, FMC Commissioner, Washington, D.C.
Peter Quinter, Chair, U.S. Customs and International Trade Law Group, Gunster, Miami, FL
Cameron Roberts, Roberts & Kehagiaras LLP, Los Angeles, CA
Stefan Kuuskne, Berkow Youd Lev-Farrell DAS LLP, Toronto, ON, CA
FMCSA Chief Counsel Jesse Elison will present on the Administration’s top issues and priorities.
Panelist: Jesse Elison, Chief Counsel, Federal Motor Carrier Safety Administration, Washington, D.C.
The American Trucking Association estimates that the trucking industry has a shortage of approximately 60,000 – 80,000 qualified drivers. It predicts that the shortage could surpass 160,000 by the end of the decade. This panel will explore differing opinions on the causes (and even existence) of the shortage, as well as emerging legal and regulatory issues that impact driver recruitment and retention. The panel will also include a discussion of best practices and technologies that help get drivers seated and keep them happy.
Moderator: Chris Merrick, Flaster Greenberg PC, Philadelphia, PA
Panelists: Andrew Poliakoff, Executive Director, Commercial Vehicle Training Association, Alexandria, VA
Matthew Leffler, Managing Partner of Armchair Attorney, LLC, Adjunct Professor of Supply Chain Law at Michigan State University, and host of the Armchair Attorney podcast, Saint Charles, Illinois
Steve Keppler, Scopelitis Transportation Consulting, Arlington, VA
This panel will address and provide tips with respect to insurance issues frequently encountered by defense counsel in transportation litigation, including obligations regarding disclosure of insurance towers, policy limit considerations, and coverage available to clients under the third-party insurance policies as additional or omnibus insureds, tenders of defense to third-party insurers, and the implications of the same on the control of the client’s defense. The panel will also discuss tips on how counsel can best position their transportation clients on the front-end through the procurement of essential insurance coverage and contractual terms relating to insurance.
Moderator: Matthew Koch, Marwedel, Minichello & Reeb, P.C.
Panelists: Brad Bertkau, Canty Novy Bertkau Gordon, LLC, Chicago, Illinois
Elizabeth Bass, Richardson Law Group, Nashville, Tennessee
Patrick Foppe, Lashly & Baer, P.C., St. Louis, Missouri
Litigation is often messy, as most litigators know. The panel will examine the many ethical issues that can arise in litigation, drawing from news-headlines, reported case law, and ethics opinions. Topics will include the allocation of authority between attorney and client, settlement discussions, court room antics, ex-parte communications, conflicts of interests.
Moderator: Matt Barrette, Blitch Westley Barrette, S.C, Chicago, IL
Panelist: Mary Andreoni, Deputy Registrar, Illinois Attorney Registration and Disciplinary Commission, Chicago, Illinois