When a reporter found Wilson, she asked about pawning the bonds.
"Yes! I remember the pawn shop!" Wilson said.
Wilson was surprised to learn that his handful of $100 savings bonds were now fully matured and worth more than $3,000.
"You could use $3,000, right?" the reporter asked Wilson.
"Yeah! Yeah!" he replied, but he remained skeptical until he got on the telephone with Mathis.
"She told me about it but I thought she was trying to trick me,” Wilson said to Mathis, who made plans to return the cash by Friday.
It was relief to Wilson, who had been turned away by crowded shelters and was desperate for a warm place to sleep for more than a week, WGN reported.
"They've been jam packed,” he said. “You just can't get in.”
With just two pairs of pants and a blanket in his backpack, Wilson said the money will be enough to get him off the street for good this winter.
"He could have kept it himself and cashed it in. I'm surprised he's going to give it back to me,” Wilson told WGN. “It means a lot because I don't have nothing. It really helps me.”