But the intertwining interests of the Trump campaign and his businesses raise some disconcerting ethical and legal questions as the race for the White House continues. This financial morass is alienating Republican donors and lawmakers who already have their doubts about the presumptive GOP presidential nominee—and raises questions about just how far Trump could theoretically go if he wanted to profit from his campaign.

“Presidential campaigns generally try to separate themselves from their businesses. What he is doing is unprecedented,” said Larry Noble, general counsel of the Campaign Legal Center. “Using all of your companies to provide services to your campaign—whether it’s illegal or not, that’s questionable… if he’s doing this to enrich himself, it is illegal.”…

Trump’s campaign is also employing a number of individuals who also have roles in the Trump Organization, the umbrella group for the likely GOP nominee’s businesses. This could profit Trump if these employees are being paid with political funds while spending time working on the business side.

If he overpays for these employees with campaign funds, he’s helping subsidize the company; if he pays them below-market rates, the company is subsidizing his campaign. This legal mess is the reason campaigns steer clear of personal businesses.