Famed lawyer Alan Dershowitz said Monday the list of open-ended questions special counsel Robert Mueller reportedly wants to ask President Trump may have been specifically drafted to trip Trump up if he provides long-winded responses.

"They are really designed to let him ramble and talk, and I suspect that's the strategy of the special counsel because they know that may be President Trump's weakness," Dershowitz told CNN.

"If they were to ask him direct, tough questions to which he can answer yes or no, that might not give them the advantage they are seeking," he continued.

The list encompasses inquiries about former national security adviser Michael Flynn, fired FBI Director James Comey, Attorney General Jeff Sessions, and possible Trump campaign coordination with Russia, according to the New York Times.

Dershowitz also advised Trump's personal attorneys to respond to as many queries as possible in writing, if permitted by Mueller, in order to prevent the president from making statements that could expose him to legal risk.

While most of the questions were predictable, Dershowitz added the line of inquiry about Trump's business transactions before he was elected could pose a problem.

"He can refuse to answer questions based on executive privilege that focus on reasons why he engaged in activities that are covered by Article II of the Constitution," Dershowitz said. "The problem is those are the easy questions and he can answer those whereas the hardest questions, the one about his financial dealings, he has no executive privilege."