At the time it seemed surreal that Montana would suit up for any other team than the one he had led to four Super Bowl victories, in which he was named the game's MVP three times.
But Montana's career in San Francisco didn't end the way many had figured it would. After sustaining an injury in the 1990 NFC Championship game, Montana would miss the entire 1991 season and a good portion of the 1992 campaign.
By the time he returned, Steve Young was entrenched as the starter.
Despite throwing for over 35,000 yards and 244 touchdowns as a member of the 'Niners, Montana was sent to Kansas City, believing he could still play the game.
As a Chief Montana came in, along with big free-agent signing Marcus Allen, and the team was primed for a deep playoff run. Montana had many questions to answer regarding his talent level after almost two full seasons of inactivity, but he answered them the way the fans who watched him for 13 seasons in San Francisco would have expected.
In '93, Montana led the Chiefs all the way to the AFC championship game, the furthest Kansas City had been in the playoffs since it went to the Super Bowl in 1969. The Chiefs lost the game to the Bills, 30-13, but Montana was clearly still the on-field leader he had always been.
The 1994 season rolled in, and expectations were high.
Montana had 3,283 passing yards that season and 16 touchdowns. More importantly, he again took the Chiefs to the playoffs, but they were defeated by Miami in the Wild Card Round.
Montana decided to retire following that season at the age of 38, ending a sure Hall of Fame career.
What parallels can be drawn between this and Peyton Manning's decision to become a Denver Bronco?
Manning recently turned 36. Despite his signing a five-year contract, will the Broncos get him for that long?
Manning played 14 seasons for the Indianapolis Colts, helping the team win the Super Bowl to cap off the 2006 season. He threw for 54,828 yards and 399 touchdowns as a Colt.
Most importantly, Manning's tenure in Indy came to a close with questions concerning his health clouding his departure.
Manning has undergone several surgeries on his neck and missed the entire 2011 season.
Reports from OTAs suggest that Manning is throwing the ball very well.
The Broncos are not at all worried about Manning's being able to bounce back and feel they will get the Manning of old.
But with his new surroundings and new teammates, will Manning return to Pro Bowl form? Will he lead the Broncos to playoffs, the conference championship or even further?
Montana was the face of his franchise for many years, as was Manning. Montana experienced success with his new team, and Manning will do the same.
In fact, Manning has a good chance to do one better than Montana: win the Lombardi Trophy for a second team.