While this year's annual RainbowPUSH conference focuses on the future of the economy, there was a look back Monday when Jackson was reunited with the men.
Each incident made news headlines at the time. Stuart Lockwood was 5 years old when he was taken hostage in 1990 while his family was living in Kuwait.
"The convoy over to Iraq was the most traumatic experience because we didn't know where we were going," Lockwood said.
The boy came face-to-face with Saddam Hussein, who wanted to pose with the frightened boy for a photo-op, but Lockwood refused.
"It was one of those things where he tried to sit me on his knee, and I just didn't fall for it," he said.
Lockwood was released after one month in captivity. Since then, the now-24-year-old has settled in Wooster england, where he's a teacher.
He flew in to Chicago to thank Jackson for his efforts and to meet Andrew Ramirez, one of three soldiers taken hostage in Serbia in 1999.
Ramirez says his captors weren't physical.
"Nothing like you see on TV, nothing like you would think, but enough where we were actually better off getting out," Ramirez said.
That time came one month later.
"We were actually awakened in the middle of the night and told, 'You're going home tomorrow,' and I didn't want to believe them until I was on a bus or somewhere else other than Serbia," said Ramirez.
Ramirez, now age 35, is also a teacher, but he lives in Los Angeles. He says he wanted a chance to say thank you for his freedom.
One more similarity between Lockwood and Ramirez is that Monday was the first time either man had been to Chicago, and they both said they hoped to take in the Taste of Chicago.