Federal investigators have confirmed that they are looking into Jackson's spending of campaign funds. There are allegations that he used those finances to decorate his home.
Candidates are required by law to itemize all their campaign expenditures. While Congressman Jackson is being investigated for the misuse of funds, for the past 10 years, there are many ways he has spent campaign money that is legal. However, some of it is considered pushing the envelope.
Jackson is known to like cigars. He was holding one when his photo was taken this week leaving his Washington, D.C., home. According to his campaign expenditures, Jackson has spent hundreds of campaign fund dollars over the years at cigar stores, either for fundraisers, an inaugural reception and in one case a cigar caucus.
"Expenditures in that area would fall into a gray area, where it would depend on if it is some way connected to his official duties or campaign expenditure," said DePaul University political science professor Zachary Cook.
Cook says the cigars are legal, according to Federal Election Commission rules, as are many of Jackson's expenditures that may be perceived as questionable.
Jackson lists many high-end hotels and restaurants as campaign expenses, but the biggest expense is the amount of money the congressman has paid his wife, Alderman Sandi Jackson.
Since 2003, Sandi Jackson's consulting firm J. Donatella and Associates has been paid monthly, totaling $429,000.
"The consultancy fees that he pays to his wife he actually got an FEC decision on that back in 2001, where he said that this was permissible, but the size of the amount he's paid his wife for consultancy fees has been unusually high," Cook said.
Sandi Jackson's mother and sister have received thousands of dollars in campaign money for their services.
While it may be pushing the envelope, Cook says it does not cross the legal line where money is being used for personal use only.
"Anything having to do with truly personal use, particularly anything having to do with your house," said Cook. "This has come up before...you're not supposed to use any kind of congressional or campaign funds to do anything that would upgrade your own residence."
And using funds to redecorate Jackson's home is being reported as the subject of a new federal investigation.
As for the legal expenditures, Jackson is not the only member of Congress to employ relatives or spend campaign funds at high-end hotels or restaurants, although there are many candidates who choose to be more conservative with their campaign funds.
Jackson's campaign nor his congressional office had comment.