He was hurt while battling a fire in the city's Burnside neighborhood.
John Anderson is now partially paralyzed, but fellow firefighters are banding together to help Anderson and his family with his mounting medical expenses.
Anderson is described as a character, known to always crack a joke.
"You're not around him very long without laughing about something," Chicago Fire Capt. Chris Steinmetz said.
Steinmetz has gotten to know Anderson very well. They're both firefighters working out of a fire station in Burnside.
At age 50, Anderson is the oldest among his colleagues. He assumed a father-figure role and took on duties as the fire house cook.
"It was one of the best things about being here, having great meals every day. He was outstanding all the time," Steinmetz said.
But now, Anderson is being looked after by his colleagues, after suffering a catastrophic injury.
On Friday night, the firefighters responded to a house fire at 90th Street and Langley Avenue, and Anderson was outside when a large object fell on him.
He is now permanently paralyzed from the waist down.
"We had just come back from a fire just before this one. So, we were just working with each other. And then, in the blink of an eye, things change," Steinmetz said.
Anderson's older brother, Roy, is among those stunned by the tragic turn of events.
Both have carried on the family tradition of being firefighters.
"His brother, father, grandfather, uncle, cousins all served in the fire department. His grandfather actually died in the line of duty in 1962," Steinmetz said.
Steinmetz said Anderson has a challenging road to recovery, but seems to be making the best of it.
"He's in great spirits; he was joking around. He was back to old John pretty much," Steinmetz said.
Steinmetz started a fundraiser for Anderson's medical expenses and home modification costs. Visit www.theyardfoundation.org/mayday/john-anderson for more information.