courtesy Creative Commons

Two of Cain’s top aides were also in charge of a private company called Prosperity USA that is based in Wisconsin. The group paid for several of Cain’s campaign expenses early on. Items paid for include iPads, chartered flights and trips to Las Vegas, the Milwaukee Journal-Sentinel reports.

Under federal election and tax laws, such payments are forbidden. Nonprofit charities are not allowed to participate or donate money or services to political campaigns, reports the Washington Post.

Prosperity USA also paid $100,000 to the Congress of Racial Equality, a conservative black organization. This payment came, according to the Milwaukee Journal-Sentinel, right before the Congress of Racial Equality featured Cain as a speaker at their annual Martin Luther King Jr. dinner in January. Cain was not paid for the appearance.

Prosperity USA said it was owed roughly $40,000 by Cain for items in February and March. The group is now defunct and it is unclear if Cain ever paid the group back. His federal election fillings give no indication that he did.

Prosperity USA was run by Cain’s current chief of staff and deputy chief of staff.

Election law experts told the Milwaukee Journal-Sentinel that the transactions raise questions for Cain and the group, which billed itself as a tax-exempt nonprofit.

"The number of questionable and possibly illegal transactions conducted on behalf of Herman Cain is staggering," Michael Maistelman, a Democrat who has represented politicians from both parties on campaign issues told the Milwaukee Journal-Sentinel.

In an interview with Fox News Cain said that he had not yet read the report, but would “look at the report and see if there is any validity.”

The allegation comes when Cain is already in the spotlight for accusations of sexual harassment.

Reach associate news editor Hannah Madans here.