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For the seventh time, Benesch is honored to announce that it has been named Law Firm of the Year in Transportation Law by Best Lawyers® Best Law Firms. This marks our 12th consecutive year (2014–2025) as a national first-tier ranked firm in Transportation Law.
Many transportation and logistics (T&L) companies are family-owned or closely held businesses that often bear their founder's name. Some have been passed down through two or more generations of family ownership. But there comes a time for most businesses when selling full or partial ownership becomes a desire or even a necessity. This article is a brief seller's road map, based on years of experience helping owners sell their businesses or take on investments, from those first thoughts of selling your business through the closing process.
Getting Your House In Order. To paraphrase the old Boy Scouts of America motto—it is always a good time to prepare. Readying a business for eventual sale can add value and alleviate the obstacles that can slow or even derail a sale process. One initial point of consideration is determining exactly what is being sold, whether it includes some or all of the business's operations and assets, and whether the assets to be sold are ready for sale in their current condition. Ensuring that all books and records are ready also eliminates stress during the all-important due diligence process, when a seller needs to demonstrate clear title to assets, payment of taxes, appropriate licensing and operating authority, and due business formation and qualification.
Kicking-Off the Process. Early discussions with buyers are usually "exploratory" in nature. They are big-picture discussions about goals and fit to see whether more substantive conversations are worthwhile. Having a nondisclosure agreement (NDA) makes perfect sense even at this early stage because you will not want the details of your business shared—including the very fact that you are exploring a potential sale or investment.
Selling Your Transportation Company? Here's the Road Map
A key consideration in any sale process is whether or not to hire a financial advisor. In our experience, engaging an investment banker experienced in the T&L industry can be very helpful, and a qualified banker's value to the process should pay for itself. The role of the banker is to help you shop your business, test the market, and help you achieve the optimal outcome in terms of value and deal terms. Depending on your objectives, the process may be aimed at a wide audience or curated to a smaller subset of potential buyers. An investment banker will help to manage the sale process from start to finish, including organizing the due diligence production inherent in every transaction.
Selecting a Buyer. While the total "top line" purchase price consideration that a given buyer proposes to pay is certainly a major factor in selecting the ultimate buyer, there are a number of other factors to keep in mind. For instance, what form will the consideration take? All cash? Cash and a Seller Note (meaning that you, the seller, are financing part of the purchase)? Or is the buyer planning to use its stock to pay part of the purchase price? If so, there are many nuanced issues to address regardless of whether the buyer is a publicly traded business or a privately owned business. And, by the way, in the case of privately owned business, there will be significant differences in the approach of a private equity-sponsored company versus a non-sponsored company (i.e., a family-owned or closely held business).
Other factors to consider are cultural fit and the role you expect to have and the roles you expect your management team to have under new ownership. And, certainly a key consideration in differentiating among buyers is certainty of closing. What items have the various buyers indicated as conditions to their ability to close— and how will they finance the transaction?
Structuring the Sale. Eventually in every transaction the subject of asset purchase versus equity purchase arises. Buyers often have strong financial, tax and liability mitigation reasons for the type of structure they prefer. The T&L industry has its own unique character since some operating authorities, licenses and permits are not easily transferrable in asset transactions. Understanding the nature of the consents required in order to convey key customer and vendor contracts is an important part of identifying the viability of an asset sale versus an equity sale transaction. As a business seller, one of your objectives is to understand the nuances of various deal structures, how they impact the likelihood of a successful sale process and, ultimately, how they may impact the legacy of your company.
Going Through the Sale Process. Once it is time to talk price and the basics of structure, then a letter of intent (LOI) is often in order. The LOI will include key terms, such as the anticipated sale price, how that will be paid, and the proposed transaction structure (asset or stock purchase). In addition, the LOI will establish the buyer's exclusivity period, during which the seller is prohibited from negotiating an alternative transaction with another buyer. The full third-party due diligence process generally kicks off at this point, and the buyer's legal, accounting, insurance and IT professionals will review your company to confirm the buyer's expectations. Negotiations will also begin on a definitive purchase agreement between you and the buyer.
Closing Considerations. Transactions generally "close" (i.e., the deal is finalized, and the purchase price consideration is delivered to the seller) concurrent with the signing of the definitive purchase agreement. In some cases, though, the purchase agreement is signed, but the transaction "closing" is delayed until certain conditions have been satisfied. For instance, government approvals, third-party consents and confirmatory customer calls may be required; however, the parties may choose to pursue those only after the signing of the definitive purchase agreement. From the seller's perspective, the latter approach is often preferred because the definitive purchase agreement has been signed and the buyer has limited "outs" to not close the transaction.
Post-Closing Considerations. Not all deals mean that the seller walks away from the business. It is frequent for sellers of T&L businesses to stick around after close under a short- or long-term employment contract or consulting agreement. Keep in mind, that if you do walk away from business, you will likely be subject to noncompete obligations, meaning that you are prohibited from starting a competing business or soliciting customers for a period of time.
No single reason exists to sell, since every company is as different as its leaders and history. Still, for almost everyone, it is an emotional once-in-a-lifetime decision. A little effort in planning ahead and bringing the right team can help steady nerves through that unfamiliar terrain.
Every Victory Is a New Beginning: U.S. Supreme Court Agrees to Consider Freight Broker Liability
On Friday, October 3, 2025, the United States Supreme Court announced that it will provide vital guidance regarding the extent to which freight brokers are liable for alleged negligence in selecting motor carriers that transport goods for brokers' customers. The announcement was immediate cause for celebration among those in the freight brokerage industry for the reasons explained below.
I. What Is the Underlying Case?
The case now before the Court is Shawn Montgomery v. Caribe Transport II, LLC. In Montgomery, a customer retained a freight broker, C.H. Robinson Worldwide, Inc. (CHR), to arrange for the interstate transportation of a load of plastic pots. CHR contracted with a federally licensed motor carrier, Caribe Transport II, LLC (Caribe), to perform the transportation for the customer. Caribe's driver veered off the road while he was transporting the load through Illinois, colliding with a tractor-trailer that was stopped on the side of the road. The tractortrailer was being driven by Shawn Montgomery, who was injured as a result of the collision.
Mr. Montgomery commenced litigation in federal district court in Illinois to recover for his injuries. He sued not only Caribe and Caribe's driver but also CHR and certain affiliates of CHR.
"As a practical matter, certain parties currently embroiled in freight broker litigation should consider seeking to stay their cases until the Court issues its decision in Montgomery."
Mr. Montgomery alleged that CHR negligently selected Caribe to perform the transportation and that CHR was vicariously liable for the torts of Caribe and its driver due to alleged control exercised over Caribe and its driver. CHR moved for summary judgment on the vicarious liability claim, which the district court granted after finding that Caribe and its driver were independent contractors—not agents—of CHR. The district court also ultimately granted judgment for CHR on the negligent hiring claims on the basis that such claims were preempted by a federal statute, the Federal Aviation Administration Authorization Act ( FAAAA). Mr. Montgomery appealed to the U.S. Court of Appeals for the Seventh Circuit, which affirmed the district court's dismissal of the negligent hiring claims.
Mr. Montgomery then sought review from the U.S. Supreme Court. Notably, despite winning at the federal district court and in the Seventh Circuit, CHR also requested that the U.S. Supreme Court review the decision in order to provide clarity to the freight brokerage industry. The Court has now agreed to hear the case.
II. What Is the FAAAA?
In the late 1970s and early 1980s, Congress began to deregulate various types of interstate transportation services, culminating in the mid-1990s with the passage of the FAAAA and the Interstate Commerce Commission Termination Act (ICCTA). The FAAAA expressly preempted a wide variety of state and local regulations and state law claims affecting motor carriers. Among other things, the ICCTA also expanded federal preemption under the FAAAA to include preemption of claims not only against motor carriers but also against freight brokers in particular. The deregulatory goal of the FAAAA was to facilitate interstate commerce by eliminating the patchwork quilt of conflicting state laws and regulations that was hampering the operations of motor carriers and brokers.
However, the FAAAA not only preempts positive laws enacted by states but also other forms of state action (i.e., court judgments and jury verdicts) that have the effect of regulating the services of freight brokers. This latter form of state regulation often presents an existential risk to the freight brokerage industry. After all, personal injury lawsuits against motor carriers and freight brokers can end with multimilliondollar verdicts. In recent years, the number of lawsuits against brokers has only increased, causing insurance premiums to skyrocket and leaving brokers confounded about what level of "due diligence" they should be applying when selecting the motor carriers that haul their customers' goods.
III. What Is the Legal Issue that the Court Will Decide?
The key legal issue that the Court will decide is whether the so-called "safety exception" in the FAAAA saves negligence claims against brokers from being preempted. As amended, the FAAAA provides:
Except as provided in paragraphs (2) and (3), a State, political subdivision of a State, or political authority of 2 or more States may not enact or enforce a law, regulation, or other provision having the force and effect of law related to a price, route, or service of any motor carrier (other than a carrier affiliated with a direct air carrier covered by section 41713(b)(4)) or any motor private carrier, broker, or freight forwarder with respect to the transportation of property.
49 U.S.C § 14501(c)(1). While courts have broadly agreed that this language preempts claims against freight brokers as a general rule, courts disagree about the meaning of one of the statutory exceptions in the FAAAA. At issue here is the meaning of the so-called "safety exception," a savings clause that provides that the FAAAA does not "restrict the safety regulatory authority of a State with respect to motor vehicles." Id. § 14501(c)(2)(A) (emphasis added).
The straightforward text of the exception seems clear enough: Under the FAAAA, states retain regulatory authority over motor vehicles, despite the otherwise broad preemption language in the statute. Stated another way, the savings clause allows states to continue to regulate the safety of motor carriers, trucks and other vehicles operating in the state.
Yet, the federal appellate courts are deeply divided over the meaning of this exception when it comes to freight brokers. Stretching the law's text to its breaking point, plaintiffs' lawyers have argued that the phrase "with respect to motor vehicles" permits states to exercise safety regulatory authority not only over motor carriers (who obviously operate motor vehicles) but also over brokers (who do not operate motor vehicles).
IV. Why Is the Supreme Court Decision so Important to Freight Brokers?
Courts across the nation have reached conflicting decisions about the extent to which the FAAAA protects freight brokers from such lawsuits.
Two federal circuits (the Ninth and Sixth Circuits) have accepted plaintiffs' interpretation and allowed state tort law claims to proceed against brokers. Those circuits include federal courts in Alaska, Arizona, California, Hawaii, Idaho, Kentucky, Michigan, Montana, Nevada, Ohio, Oregon, Tennessee and Washington. Two other federal circuits (the Seventh and Eleventh Circuits) have rejected that approach, holding that the so-called safety exception covers only motor carriers, not brokers, meaning that claims against brokers remain preempted. Those circuits include federal courts in Alabama, Florida, Georgia, Illinois, Indiana and Wisconsin. District courts in other circuits and state courts across the country have likewise issued differing opinions.
The resulting landscape leaves brokers subject to a dizzying array of conflicting standards across the country. For instance, a freight broker sued in federal court in California or Ohio remains exposed to negligence claims. However, if the same freight broker is sued in federal court in Illinois or Florida, the freight broker is protected from negligence claims. Freight brokers cannot function effectively in an environment where liability depends on how far the chosen motor carrier made it down the road—and in which federal Circuit that road lies—when an accident occurs. Without a single, uniform ruling about the meaning of the so-called "safety exception" in the FAAAA, brokers are simply left to guess about what law governs their businesses.
The U.S. Supreme Court has now agreed to resolve this deep divide over an issue that is of exceptional public importance. The Court's eventual decision will bind not only federal courts but all state courts as well.
V. When Will the Court Issue a Decision?
Persuading the Court to accept a case for review is an achievement in and of itself, since the Court only accepts a small handful of the many thousands of petitions submitted for review each year. However, CHR must now persuade the Court on the merits of the issue. The granting of certiorari kicks off a schedule that, absent any extensions, will extend well into the new year.
Mr. Montgomery's merits brief will be due in mid-November, and CHR's brief will be due thirty (30) days afterward in mid-December. Mr. Montgomery is entitled to a reply brief that will be due in mid-January 2026. Likewise, any amicus briefs supporting either party must be filed within seven (7) days of the date on which the party supported by the amicus filed its merits brief. The Court will schedule an oral argument to occur after briefing is complete. Oral arguments are generally scheduled on specified Monday, Tuesday and Wednesday mornings between now and the end of April. The Court issues its decisions weeks to months after oral argument depending on the Justices' respective workloads and the number of concurring and dissenting opinions.
Regardless, the Court will issue a decision before the Court's summer recess in late June or early July of 2026.
VI. Are Any Other Cases Pending Before the U.S. Supreme Court on This Issue?
Total Quality Logistics, LLC (TQL) has a petition for review pending before the U.S. Supreme Court on the very same legal issue. Whereas the court decision in Montgomery held that the negligence claims against CHR were preempted, the court decision in TQL v. Robert Cox held that the negligence claims against TQL were not preempted. When the Court granted certiorari in Montgomery, the Court did not announce what it will do with the petition in Cox. Several possibilities exist.
First, the Court could consolidate, group or otherwise link the petition in Cox with the petition in Montgomery, since the two petitions obviously raise the same core legal issue, albeit from different procedural postures and with subtle distinctions in the respective petitioners' arguments. Second, the Court could let Cox linger on the docket without any action and then, upon disposition of Montgomery, "GVR" the petition in Cox (meaning "grant" certiorari, "vacate" and "remand" based upon the decision that it renders in Montgomery). Third, the Court could simply treat Montgomery as the effective "stand-in" for Cox (while not expressly stating so) and deny cert in Cox, which would seem counterintuitive but is possible.
Regardless of the procedural treatment of Cox, the core issue is now going to be addressed by the U.S. Supreme Court.
VII. What Does This Mean for the Industry in the Meantime?
When issued, the Court's decision will have a profound effect upon the way in which brokers perform their core service of selecting and arranging motor carriers to transport freight.
In the meantime, while the briefing and oral argument unfold over the upcoming months, various interest groups on both sides of this issue will begin preparing amicus briefs to support or oppose a particular outcome in the U.S. Supreme Court. As a practical matter, certain parties currently embroiled in freight broker litigation should consider seeking to stay their cases until the Court issues its decision in Montgomery. Underwriters who insure the freight brokerage industry should begin planning for various possible outcomes in Montgomery and evaluating what effect those possible outcomes could have on reserves and future premiums.
Motor carriers must also assess how to prepare for the Court's eventual decision; a reversal of Montgomery would effectively eliminate some motor carriers from the transportation market altogether, since brokers would be driven to work with only the most established motor carriers. Shippers, who themselves have benefited from FAAAA both directly and indirectly, will also begin evaluating the effect that a favorable or unfavorable decision will have upon their procurement of transportation services. And, of course, forward-thinking freight brokers will be workshopping the ways in which they will operate going forward depending on the Court's decision.
In short, while the granting of certiorari in Montgomery is truly momentous news for the freight brokerage industry, this victory is simply the beginning of a new phase of the important fight to preserve Congress's deregulatory goals in enacting the FAAAA.
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