3. Sid Luckman
This is where your opinions might change as a fan, because Sid Luckman could still be looked at as the best quarterback the Bears have ever had if you're considered one of those "old heads," as the kids say these days.
As the number two overall pick back in 1939, Luckman came to Chicago by way of Columbia University.
Luckman spent his entire 12-year career with Chicago, earning All Pro honors on five occasions. He played from 1939 to 1950. On four separate occasions, the Bears great led the league in passing yards per game. Luckman finished as the league leader in passing yards, yards per attempt, passer rating and passing touchdowns three times. He also led the league once in completion percentage.
He did a whole lot of good as the Bears quarterbacks back when the game was still early on and developing into what it's become today. There is something to be said about everything Luckman was able to accomplish so long ago, along with his loyalty to the Bears organization.
His name will always bring positive, heartwarming feelings to Chicago fans for those reasons. And, he also sits number two on the team's all-time passing yardage list with 14,686 yards. Luckman was inducted into the Pro Football Hall of Fame back in 1965.