The six-time Super Bowl champion appeared on the show Thursday. After a conversation, Kimmel asked Brady about the strength of his arm.
"Do you feel like your arm is as strong as it ever was?" Kimmel asked.
Brady said yes, before Kimmel asked him to prove it. Brady and Kimmel walked outside of the studio and joked about knocking down a column of the building with a football.
They opted to jump inside of a Taxi and take it to Damon's home. Once they exited the taxi, Kimmel asked Brady if he could throw the football through a second story window on the home.
Brady pulled the football back and launched it through the window, smashing the glass.
Damon came out and asked who threw the football, but didn't appear to care after Brady admitted to breaking the window. The Patriots fan then asked to take a photo with Brady. Kimmel held his phone to take the photo, before throwing the device through one of Damon's first floor windows.
Brady took the taxi back to the set to continue his conversation with Kimmel.
The future Hall of Famer also spoke about his fans, his wife Gisele's income and how he wants to keep winning Super Bowls.
"I think the thing I've always felt for me in my life, winning has been a priority and my wife makes a lot of money," Brady said.