Stuart Levine, a longtime political insider himself, has been on the witness stand for five days, detailing at times his 30-year history of drug abuse and propensity toward bribes and illegal scams against even those close to him.
Cellini's lawyer, Dan Webb, zeroed in on the fact that a key conversation in which prosecutors say the two hatched the alleged plot wasn't recorded by investigators.
In testimony last week, Levine, whose credibility is under attack by the defense, said he asked Cellini, an influential behind-the-scenes player in state government for decades, to help him extort producer Thomas Rosenberg, who also had significant business with the state of Illinois. Cellini agreed to the scheme, Levine said.
Cellini faces federal charges of attempted extortion and fraud; he is accused of conspiring with Levine to squeeze Rosenberg to make a $1.5 million contribution to then-Gov. Rod Blagojevich's campaign.
Levine testified he and Cellini had made a deal with Blagojevich advisers Antoin "Tony" Rezko and Christopher Kelly to keep their influence in state government.
Levine was a corrupt member of the state Teachers' Retirement System board, which was to decide if Rosenberg's management firm would continue to invest $220 million for TRS. He appeared to be a ripe target for extortion but balked at making a $1.5 million contribution to Blagojevich to keep the state business, prosecutors allege.
In his third day of cross-examination, Webb walked Levine through the transcripts of several conversations recorded in May 2004 and repeatedly asked Levine to tell the jury precisely where Cellini agreed to the extortion of Rosenberg.
At one point, Webb asked Levine whether in a May 7 call Cellini ever agreed to ask Rosenberg for the cash so that he could protect his state business.
"Not those exact words," Levine said.
When Webb queried Levine about the key conversation with Cellini that wasn't recorded, he suggested Levine's drug-addled memory could be an issue.
"As you sit here, seven years later, you remember that?"
Levine answered yes.
Webb also quizzed Levine about details he kept from Cellini — like how much the extortion amount should be.
Levine never wavered from his contention, however, that Cellini was involved in the plot from the start.
"I believe Mr. Cellini understands the true nature of this conversation," Levine said in reference to one of the calls.
Several other witnesses have testified about Cellini's reach at TRS, suggesting that he had a motive to protect his influence there.
The government has highlighted moments in the tapes in which Cellini talked to Levine about Rosenberg and his pending TRS deal.
In one recording, Cellini talked to Levine about how to deal with Rosenberg, who had become angry about the alleged extortion. Cellini advised his longtime confidant on a compromise.
In another, Cellini was heard sharing with Levine some advice he gave Rezko and Kelly about what to do if law enforcement came calling to ask if they knew him.
"Just know before they ask that question that they have already checked all your phone logs," Cellini is heard saying in the call.
Neither realized then that federal investigators were secretly recording Levine's conversations at that point.
The cross-examination of Levine could wrap up Wednesday.