The U.S. Supreme Court devoted spent more than an hour and a half on Wednesday chewing on a trademark question that pits the iconic Jack Daniel's trademark against a chewy dog toy company that is making money by lampooning the whiskey.

Ultimately the case centers on.....well, dog poop.

Lisa Blatt, the Jack Daniel's lawyer, got right to the point with her opening sentence. "This case involves a dog toy that copies Jack Daniel's trademark and trade dress and associates its whiskey with dog poop," she told the justices.

Indeed, Jack Daniel's is trying to stop the sale of that dog toy, contending that it infringes on its trademark, confuses consumers, and tarnishes its reputation. VIP, the company that manufactures and markets the dog toy, says it is not infringing on the trademark; it's spoofing it.

What the two sides argued

The toy looks like a vinyl version of a Jack Daniel's whiskey bottle, but the label is called Bad Spaniels, features a drawing of a spaniel on the chewy bottle, and instead of promising 40% alcohol by volume, instead promises "43% poo," and "100% smelly." VIP says no reasonable person would confuse the toy with Jack Daniel's. Rather, it says its product is a humorous and expressive work, and thus immune from the whiskey company's charge of patent infringement.

At Wednesday's argument, the justices struggled to reconcile their own previous decisions enforcing the nation's trademark laws and what some of them saw as a potential threat to free speech.

Jack Daniel's argued that a trademark is a property right that by its very nature limits some speech. "A property right by definition in the intellectual property area is one that restricts speech," said Blatt. "You have a limited monopoly on a right to use a name that's associated with your good or service."

Making the contrary argument was VIP's lawyer, Bennet Cooper. "In our popular culture, iconic brands are another kind of celebrity," he said. "People are constitutionally entitled to talk about celebrities and, yes, even make fun of them."

No clear sign from justices

As for the justices, they were all over the place, with conservative Justice Samuel Alito and liberal Justice Sonia Sotomayor both asking questions about how the first amendment right of free speech intersects with trademark laws that are meant to protect brands and other intellectual property.

Assume, asked Sotomayor, that someone uses a political party logo, and creates a T-shirt with a picture of an obviously drunk Elephant, and a message that says, "Time to sober up America," and then sells it on Amazon. Isn't that a message protected by the First Amendment?

Justice Alito observed that if there is a conflict between trademark protection and the First Amendment, free speech wins. Beyond that, he said, no CEO would be stupid enough to authorize a dog toy like this one. "Could any reasonable person think that Jack Daniel's had approved this use of the mark?" he asked.

"Absolutely," replied lawyer Blatt, noting that business executives make blunders all the time. But Alito wasn't buying it. "I had a dog. I know something about dogs," he said. "The question is not what the average person would think. It's whether this should be a reasonable person standard, to simplify this whole thing."

But liberal Justice Elena Kagan and conservative Justice Neil Gorsuch repeatedly looked for an off ramp, a way for this case to be sent back to the lower court with instructions to either screen out or screen in some products when considering trademark infringement.

Kagan in particular did not find the dog toy remotely funny.

"This is a standard commercial product." she said. "This is not a political T-shirt. It's not a film. It's not an artistic photograph. It's nothing of those things."

What's more, she said, "I don't see the parody, but, you know, whatever."

At the end of the day, whatever the court is going to do with this case remained supremely unclear. Indeed, three of the justices were remarkably silent, giving no hints of their thinking whatsoever.