Republican Donald Trump has so far paid $7.7 million in campaign contributions to his own companies and children, according to a filing with the Federal Elections Commission, and as the campaign transitions to the general election those payments are increasing. In May, they totaled at least $1.1 million—nearly 20 percent of all campaign spending that month—and in July, another $800,000 came into the Trump brood.

Campaign finance laws on the topic are hazy and contradictory, largely because no candidate for federal office has ever had such a sprawling business empire that could be employed for a campaign. The FEC allows candidates to rent themselves their own office space—as the Trump campaign does at Trump Tower—but bans them from collecting royalties on any memoirs purchased by the campaign. Money ultimately flows back to the candidate in both cases but the FEC has issued divergent rules.

Nevertheless, when it comes to payments to relatives or family-owned companies, the Trump campaign is breaking new ground. "The extent of Mr. Trump's use of his own companies for goods and services during the campaign is unprecedented," says Paul S. Ryan, a campaign finance expert and the Deputy Executive Director of The Campaign Legal Center. "It has the potential to transfer donations to himself and his children."

In July alone, Trump's campaign paid $169,758.33 in rent to Trump Tower Corporation LLC, $48,239.77 for rent and catering at Trump National Golf Club in Weschester, $1,000 to Trump Restaurants LLC, and $428.53 worth of Trump's bottled water Trump Ice. In May, Trump's campaign spent $3,938.58 at the vineyard run by his son Eric. Campaign dollars are also funneled to allies of Trump's children. Each month, the campaign spends millions on apparel like the "Make America Great Again" trucker hats. The manufacturer, Ace Specialties, is owned by Christl Mahfouz, a board member on Eric Trump's charitable foundation.

The intertwining of campaign and business takes shape in other ways. The day after daughter Ivanka gave her speech at the Republican convention wearing a dress from her eponymous fashion line, she tweeted about where people could buy it (Nordstroms.com and Macys.com quickly sold out).