In June 1997, his gun turned on then-police captain Morales, who was working undercover.
"We're trying to kill each other," Morales recalled.
More than 20 years later, they say hello with a smile and a warm hug.
"I once hated anything that stood for authority here I was embracing authority now," said Armour.
Now the men share a common goal- making Milwaukee safer starting with the next generation.
"I grew up like a lot of people, kind of. Not everybody, but a lot of people in my neck of the woods grow up," explained Armour. "There was a lot of abuse, there was a lot of abuse mentally, physically and emotionally. So, I kind of grew up kind of hating all forms of authority," he said.
The men believe that's the root of so many issues Milwaukee faces.
"They're born into a life that they're going to lose," said Morales.
"Since I was hurting," Armour said. "I began to try to lash out at other people."
The men agree their story can't be told without acknowledging the ongoing debate in Milwaukee surrounding trust and community policing. Morales said the men each have a different type of credibility.
"He's got that credibility and some people call it street creds and I believe on my side I have the credibility to influence the police department," he said.
It's a reminder both men hope the community and those in uniform remember after the deadliest year for Milwaukee Police in 20 years.
"In [Officer Michael] Michalski's ceremony I brought this up, it's easy to lose focus what our responsibility and our job is," said Morales.
"I thought right away, 'man this is going to really stir the pot,"Armour said. "To kind of go backwards, almost like, you get one of us, we get one of you kind of thing," he elaborated.
But the men hope understanding prevails. They want to see community-based work mend the broken pieces of the city and build up the next generation.
"This is a huge story in my life," Morales said. "But there's stories like this in the City that we have to show. Bring back those people that are true that went through a dark stage in their life and were able to live through it," he said.
"You see an old rundown building and then a few years later you come back and somebody sees some magnificent beautiful building," described Armour. "That's just how I examine my own beautiful life."