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They literally spent a decent chunk of money spinning up a line of business that could only make money if the tariffs were illegal.

> Did they know it was illegal

it doesnt have to be black and white. they knew enough to spin up a business that when it is overturned they could make money... which means they knew the probability was high.

even if they were not sure 100%, the fact that introducing the legislation is connected to him making money is a conflict of interest.

That's not really the comparable here, you need to find a person with vested interest in the outcome of the student loan forgiveness program.* Someone that was working within the agency responsible for the program and actively was in the discussions where the legality was discussed. Then made a scheme to financially get rewarded. Not only that used his son as a way to create the illusion of separation.

* And not just a borrower that wouldn't be anywhere similar to this level of conflict.