That is a reasonable view. I think that comment by Trump can be read many ways, depending on one's biases. 

But, the reason I give it the spin I did was because of his past comments. He belittled working poor people for not paying taxes. Their not paying taxes is also fully within the law, but he clearly does not think of them as smart for not paying taxes. So from this we know that following the law by not paying taxes is not sufficient to be smart in Trump's view.