How Caleb Williams’ Breakout Changes the Chicago Bears’ All-Time QB Rankings

Ranking the greatest quarterbacks in Chicago Bears history is a complicated exercise. It's impacted by era, scheme, and overall league context.

Still, I had to try.

Here's my best swing at the Chicago Bears' top five list following Caleb Williams' breakout 2025 NFL season.

5. Erik Kramer (1994-1998)

Kramer's peak was brief but impactful for the Bears. His 1995 season was the best in franchise history until Caleb Williams' 2025 campaign. It culminated in a Pro Bowl selection and a Bears playoff berth. In a franchise defined by defense-first football, Kramer delivered one of its rare quarterback-led seasons.

4. Jay Cutler (2009-2016)

Cutler is the Bears' all-time leader in passing yards and touchdowns, a reflection of both his rare longevity and Chicago's futile history at the position. Though the Bears were inconsistent as a team with Culter at the helm, he did lead the Bears to an NFC Championship appearance and often carried an offense that lacked a quality supporting cast.

3. Jim McMahon (1982-1988)

McMahon's legacy is defined by winning. He was the starting quarterback of the 1985 Bears, one of the most dominant teams in NFL history, and led Chicago to its lone Super Bowl title. While his career stats were modest, his toughness, leadership, and postseason resume remain undeniable.

2. Caleb Williams (2024-present)

By the end of his second NFL season, Williams had already broken the Bears' single-season passing record and came just shy of becoming the team's first 4,000-yard quarterback. Under Ben Johnson in 2025, Williams showed clear growth as a passer and playmaker, helping guide Chicago to the playoffs and emerging as the long-term face of the franchise. Perhaps this is a bit of a projection pick, but I feel good about it.

1. Sid Luckman (1939-1950)

Luckman remains the gold standard for quarterbacking in Chicago. He led the Bears to four NFL championships and was the central figure in George Halas' modernization of the passing game. Luckman retired holding multiple league records and was later inducted into the Pro Football Hall of Fame.