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It is never possible to know for certain how justices may vote based on their questions at oral argument, and the new virtual format the court has taken to in response to Covid-19 has made speculating somewhat trickier.

Harrington noted that a general rule of thumb is that justices tend to ask more questions of the side they are less likely to vote for. So far, though, justices have been asking about the same number of questions to each side in arguments conducted by phone, she said. 

One clue came last month, when the justices asked attorneys to provide more arguments about something called the “political question doctrine.”

The doctrine refers to the practice in which courts sometimes decline to rule on heated political issues. If the court says it cannot rule in the congressional cases, that could effectively be a loss for Trump, who is asking the justices to prevent the subpoenas for his records from going into effect. 

“I could see, for example, somebody like [Chief Justice John] Roberts, maybe not wanting to rule directly against Trump but saying I do not want to get involved,” said Elliot Mincberg, a former chief counsel for oversight and investigations for the House Judiciary Committee. 

Experts say there are other lines of inquiry they will be watching closely. 

“I think the key questions to Congress will be: What is the valid legislative purpose for seeking these records?” said Hans von Spakovsky, a senior legal fellow at the Heritage Foundation’s Center for Legal and Judicial Studies. 

If the justices seem skeptical of the congressional committees’ reasoning for the subpoenas, that could doom their case. 

On the other hand, Chemerinsky said that if the justices focus on the fact that the activity being investigated predates Trump’s time in office, “I think that it would be a bad sign for the president.”

Cole, of the ACLU, said that he will be listening for whether the justices seem to be looking for common ground. 

“Are the justices simply lining up on partisan sides, or are they searching for principles that would allow them to rise above partisan division?” he said.