For a billionaire businessman, Donald Trump’s presidential campaign is a financial mess. According to Trump’s latest Federal Election Commission filing, released Monday night, the presumptive Republican nominee collected less than $6 million in May (including $2.2 million he loaned himself), and finished the month with just $1.3 million cash on hand. (Hillary Clinton, meanwhile, raised $28 million over the same period, and headed into June with more than $42 million.) And the details of Trump’s screwball financials only get stranger from there, including a wrinkle that invokes those fictional gray-flanneled ad men of peak TV past, Don Draper and Roger Sterling.

Of the $6.7 million that Trump paid out last month, roughly $1.1 million was funneled back toward Trump’s companies or toward reimbursements for his children on the campaign trail, including $350,000 spent on his personal jet. His golf courses received about $65,000, while his son Eric Trump’s wine company nabbed about $4,000. Another $125,000 was spent on Trump restaurants. And of the roughly $830,000 spent on event staging and rentals, the biggest expenditure was for Trump’s own Mar-a-Lago resort in Palm Beach, Florida. One wonders if he got a good deal.

Among the odd assortment of vendors listed on Trump’s F.E.C. filing, perhaps the strangest expenditure is for an advertising firm called Draper Sterling—an apparent reference to the fictional Mad Men ad agency—which received $35,000 in late April for “web advertising.” According to its limited-liability-company registration application, Draper Sterling LLC was formed as a consulting business in December 2015, and was registered with the state of New Hampshire in March 2016. The company is registered to Jon Adkins, the co-founder of Dynamic Solutions, a consulting firm, and more recently, XenoTherapeutics, an “early stage medical device and research company,” according to his LinkedIn. Reached by telephone, a man who identified himself as Adkins declined to comment on what Trump’s $35,000 went towards.

And the story gets stranger still. Adkins’s medical device company was co-founded by Paul Holzer, a Dartmouth medical student who worked on the gubernatorial campaigns of Charlie Baker in Massachusetts and John Brunner in Missouri. As ThinkProgress’s Judd Legum reports, Draper Sterling LLC is owed $56,234 by Patriots For America, a super PAC involved in the Missouri governor’s race. That PAC is run by Adam McLain, who is Holzer’s brother. The “mysterious” and “highly unusual” debt is highlighted in a F.E.C. complaint against Patriots For America, which allegedly spent the money on “business consulting.”

Legum, attempting to pin down the connection between Trump, Adkins, Holzer, and McLain, ends up even further down the rabbit hole: