Alexi Giannoulias has big trouble ahead.

The wealthy, young, telegenic Democratic candidate for state treasurer scored a decisive victory in all regions of the state over Paul Mangieri in Tuesday’s primary. U.S. Sen. Barack Obama appeared in his TV ad.

Giannoulias has repeatedly claimed that his experience working at his family’s bank makes him qualified to be state treasurer, but late questions have arisen about some loans the bank made to an ex-mobster, and the candidate’s response has cast doubt on whether Giannoulias is ready — or even fit — to hold statewide office.

Michael “Jaws” Giorango was apparently a member of the old Chicago Heights mob operation. Years ago, he was convicted twice on bookmaking charges. One of the bookmaking operations he worked for used “threats of bombings, beatings and robbery to collect unpaid debts,” according to the Tribune.

Then, in 2004, Jaws Giorango was busted again, this time for promoting a nationwide prostitution ring through a hotel he co-owns in Florida. His interest in that hotel was at least partially financed with millions of dollars lent to him by Giannoulias’ family bank.

There have been no suggestions that either the young Giannoulias or his bank knew what was going on at the Florida hotel, or that the bank did anything illegal. But when pressed about the connection at a press conference, Giannoulias’ answers left many shaking their heads.

After saying he had met Jaws Giorango at the bank “a few” times, Giannoulias launched into a bizarre defense of the man. 

Giannoulias called the ex-con “a very nice person,” and then kept right on flapping his gums. “Is he a crime figure?” Giannoulias asked reporters. “I don’t know what the charges are that makes him this huge crime figure.”

It’s completely unbelievable that Giannoulias had no idea that the former bookie was a convict. Crain’s Chicago Business published a high-profile piece about the connection well before the press conference, so Giannoulias had to have known that the subject would be brought up.

His campaign staff played off Giannoulias’ remarks as simply a “gaffe” made by an inexperienced candidate. That response only bolstered my long-held belief that politically inexperienced rich people usually make lousy statewide candidates. If they started lower on the rung, the media and their opponents would have a chance to examine their backgrounds before they moved up to higher office.

But starting at the bottom, or even the middle, is usually beneath them. And that means we end up with disasters like Democratic US Senate wannabe Blair Hull, who spent $30 million but won just ten percent of the vote in 2004 because it came out that the cops were called after he allegedly hit his wife.

Or Jack Ryan, who had to drop out of the US Senate race after he won the 2004 Republican primary when his divorce records were unsealed.

The revelations about Giannoulias are emerging so late in the campaign that they may not impact Tuesday’s primary. His personal wealth and Obama’s endorsement may drown out most of the negative coverage.

But there is more to come about the Giannoulias family bank’s ties to Jaws Giorango, like how the bank lent $3.9 million to a Giorango family member last year. Most of that money, $3.4 million, was also loaned to a person with a Greek surname who appears on official records as an investor in that Florida hotel. 

Or how, according to official records, one of the other investors in that very same Florida hotel was Spiros Naos. Naos became such a controversial figure in the treasurer’s race a couple of weeks ago that Giannoulias was forced to return his campaign contribution. Naos’ uncle owned a casino fleet in Florida that he sold to disgraced Washington, DC lobbyist Jack Abramoff. The uncle was gunned down Gangland style after he sold the fleet. Later, Spiros Naos bought the fleet back.

There’s no real indication that the Giannoulias family bank did anything illegal. The younger Giannoulias didn’t even work at the bank when most of this stuff went down. But his public defense of Jaws Giorango puts all of this on his shoulders and guarantees a lot more media coverage down the road if he wins Tuesday’s primary.

And that’s why I think, like Jack Ryan before him, Giannoulias may not even make it to November despite his win on Tuesday.

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Rich Miller also publishes Capitol Fax, a daily political newsletter. He can be reached at thecapitolfaxblog.com