There was a stretch of questioning of Theodore Boutrous during oral arguments Wednesday before the U.S. Supreme Court on Montgomery vs. Caribe Transport II, the possibly groundbreaking case involving broker liability, that very likely made the 3PL community nervous.

Boutrous is the outside counsel for C.H. Robinson (NASDAQ: CHRW), the 3PL that hired Caribe, which in turn had a truck that struck and seriously injured truck driver Shawn Montgomery on the side of an Illinois road in 2017. Boutrous, a partner with the Los Angeles office of law firm Griffin Dunn, was taking questions from the judges about his interpretation of the Federal Aviation Administration Authorization Act (F4A), the transportation-focused law from 1994 with sections that could be interpreted to be at odds with each other.

Justice Elena Kagan, who over the course of the roughly 90-minute proceedings sounded largely sympathetic to the idea that brokers could be held liable or negligent for safety issues involving trucks they hired, said she was making an admittedly 'simple-minded way of looking at this.'

The question before the court, and the circuit courts whose conflicting decisions led to this seminal moment Wednesday, was whether the safety exception in F4A opened the door to brokers being dragged into lawsuits over carrier safety.