"It's Uncle Joe's money?" Orlando asked in the 2002 conversation, recorded by the FBI.
"Yeah," Canalichio said.
Federal prosecutors on Friday played that tape - and a handful of others - in a bid to persuade jurors that even the smaller loans were part of a larger organized gambling, extortion and loan-shark racket controlled by Ligambi and his associates, and that the money flowed up.
The testimony came on the second day of Orlando's coming out as a government cooperator at the trial for Ligambi, Canalichio and five others. It was also his first day of cross-examination, and the lawyers pounced.
Under questioning from Ligambi's lawyer, Orlando conceded he was never beaten over his mounting debt, and that he never saw Canalichio or others on trial beat someone else who owed them money. He also agreed that tough talk and name-dropping is routine in South Philly, the false currency that people trade to get things done.
The lawyer, Edwin Jacobs, Jr., suggested that Orlando deliberately inserted Ligambi's name into the conversation that day, when Canalichio could have been referring to someone else named Joey.
"You were a cooperating witness for the government, and you knew darn well what they were trying to do was get something on tape that implicated Joe Ligambi," Jacobs asserted.
Orlando denied it.
"I was not instructed to use his name, Uncle Joe," he said "That's not true."
Often looking toward the defendants, Orlando, 45, has portrayed himself as tortured over the decision to cooperate.
Canalichio, he said, was "a dear friend." Reputed underboss Joseph "Mousie" Massimino had his utmost respect, "treated me very well" and may have intervened to keep one particularly aggressive loan shark off his back.
But Orlando told jurors he felt like he had no choice after learning in 2001 that his half-brother had been wearing a wire and gathering evidence against mobsters, including when he paid off some of Orlando's debts.
The defense lawyers have argued the case is built on fabrications from criminals trying to save themselves.
At the time he began cooperating, Orlando owed thousands of dollars to several sharks, loaned at 30 percent interest that compounded weekly.
"One of the reasons you had debt was because you're a complete gambling degenerate, isn't that right?" said Canalichio's lawyer, Maggie Gross, delivering a point Orlando didn't contest.
Jacobs noted that Orlando had admitted staging a fake auto accident, running a credit scam, selling drugs and robbing a drug dealer - but that none of the proceeds went to the defendants who prosecutors contend controlled South Philadelphia crime.
He parsed the plea agreement, one that Orlando signed with prosecutors after being charged in the credit scheme almost a decade ago. He faced up to 16 months in prison under federal sentencing guidelines, but ended up getting probation.
"The bottom line is that for the bank fraud, drug dealing, the robbery, bogus auto accidents . . . The total time you did in jail is what, zero? Not a day in jail?" Jacobs asked.
"I put my life at risk just wearing a wire," Orlando said. "I put my life at risk here today testifying. That's enough to do. For the rest of my life I have to look over my shoulder."
"But not one day in jail, right?" Jacobs shot back.
"Not one day in jail," Orlando conceded, "but maybe a bullet in my head someday."
Orlando has spent nearly a decade in the witness protection program. He said he is married with children and a steady job in another state.
"Can you ever come back to Philadelphia?" Assistant U.S. Attorney John Han asked.
"Absolutely not," Orlando said. "What I'm doing here today will be my death sentence."
His testimony is scheduled to resume Tuesday.
Contact John P. Martin at 215-854-4774, at firstname.lastname@example.org, or follow @JPMartinInky on Twitter.