Last night, Illinois’ State Treasurer Alexi Giannoulias addressed the DNC, talking about his “friend and mentor”, Barack Obama, and calling for “a new type of leadership.” Giannoulias said that Obama has great integrity, yet the association between the two men raises questions along the lines of (and related to) convicted felon Tony Rezko.

Obama and Giannoulias have been mutual supporters, politically and otherwise, for at least five years, with Giannoulias having contributed $7,000 to Obama’s campaign for the Illinois State Senate seat in 2003 and 2004, an interesting choice for a man who was simultaneously giving $17,000 to the National Republican Congressional Committee.

Giannoulias, who was called Obama’s “protégé” in a Chicago-based publication, has also served as the National Chairman of Greeks for Obama Committee. The organization’s Vice Chairman, Michael Karloutsos, also has a history of supporting Republicans, including a donation to Rick Santorum and Bush-Cheney ’04. He was also a Pioneer for President George W. Bush, meaning he raised at least $200,000 for the Bush-Cheney ’04 ticket. In the past year, he switched his party affiliation “from R to D”.

Giannoulias also hosted a fund-raiser for Obama in Chicago in September, 2007, omitting it from his public schedule and keeping it closed to the press. Could it be that Obama didn’t want the press asking questions about a New York Post article published that same morning entitled “Obama's Mob-Tie $idekick”?

The NY Post story references the many questions about Giannoulias’ ties to organized crime through Broadway Bank, a Chicago bank that his family owns and where Alexi Giannoulias listed himself both as President and as Chairman of the Board on FEC filings surrounding the campaign contributions mentioned above.

According to a Chicago Tribune article from 2006, Giannoulias “has faced questions about the bank’s multi-million dollar loans to Michael Gioranago, a convicted bookmaker and prostitution ring promoter.” Barack Obama was quoted in the article as saying that he “is concerned by revelations that the bank owned by Illinois Democratic treasurer nominee Alexi Giannoulias' family gave loans to a Chicago crime figure and said the candidate owes him and the public a full accounting.”

And while Giannoulias claimed that the loans to Gioranago were made “before he became a full-time bank employee”, “newly discovered public records show Broadway Bank made $11.8 million in additional mortgage loans to Giorango just last year. Giannoulias said he oversaw the servicing of those loans.”

Giannoulias also appears to have lied about the bank's financing of a casino boat marina. And in what may or may not be an ugly coincidence, convicted felon Tony Rezko racked up $450,000 in gambling debts by writing bad checks on his Broadway Bank account. According to Crain’s Chicago Business, “Obama kept his 2004 Senate campaign funds” at Broadway Bank as well.

Giannoulias himself has accepted at least one controversial campaign contribution, from Spiros Naos, an owner of a line of gambling cruise ships, who got ownership of the company after his uncle “was gunned down in an execution-style slaying after selling the gambling fleet to a group that included indicted Washington lobbyist Jack Abramoff”, according to the Chicago Daily Herald. After initially defending the contribution as one Greek helping another, Giannoulias eventually returned the money once the media began dogging him about it.

We know what Giannoulias has done for Obama. What about the other way around? Why would a man with banking ties to organized crime (and a man who had generally not contributed to Democrats) become such a big supporter of Barack Obama?

Much in the same way that Obama was groomed for his elections by people in power in Chicago, and much in the same way that Obama supported the corrupt Stroger family even when he could have supported a reform-minded (liberal Democrat) opponent to the Strogers, the Obama-Giannoulias relationship seems one of political payback.

Obama endorsed Giannoulias for State Treasurer when the latter was just 29 years old, but the NY Post reported that “Giannoulias is so tainted by reputed mob links that several top Illinois Dems, including the state's speaker of the House and party chairman, refused to endorse him even after he won the Democratic nomination with Obama's help.” Obama remained a big supporter and is credited with having been an important factor in Giannoulias’s victory.

But, as Crain’s asked, “[J]ust why did Sen. Obama last week endorse for Illinois treasurer an unknown 29-year-old whose financial experience is limited to working at a family-owned Chicago bank, and who, as recently as five years ago, was shooting professional hoops as point guard with team Panionios of Athens, Greece?”

Media reports say that Obama was grateful for Giannoulias’s early support of Obama, including the six-figure fund-raising for Obama’s first campaign. But what about be the mutual connection to Tony Rezko, and could there be other connections we don’t yet know about?

Giannoulias has clearly believed he had something to gain. As someone who lived in Chicago for 15 years, I know that politics general and Chicago politics in particular is about who can help people make money or gain power. One way in which Obama could return the favor of political support to Giannoulias would be to support the possibility that Giannoulias could be selected to fill Obama’s US Senate seat if Obama wins the presidency.

The close association of Obama with a man who seems clearly to be involved in some shady deals with convicted criminals is yet another example of questionable judgment at best and typical dirty Chicago politics at worst. I wonder if Giannoulias will turn out to be the next in Obama’s never-ending series of “He’s not the man I knew”.