The Kansas City Chiefs don’t have the most prestigious history when it comes to the quarterback position. The Chiefs franchise is mostly based on running and defense; however, there have been a number of great quarterbacks to wear a Chiefs’ uniform.
5. Bill Kenney
77.0 Passer Rating
Kenney played every game of his career in a Chiefs’ uniform, and he proved a lot of people wrong. He was drafted in the 12th round by the Miami Dolphins in 1978 but was cut immediately. The Chiefs took little risk in signing Kenney and he responded. Despite drafting Todd Blackledge No. 7 overall in 1983, it was Kenney who would start and excel as the Chiefs starter for the next few seasons. His 4,348 yards was a franchise record until 2004.
A great story but Kenney wasn’t the most consistent and in his only playoff appearance against the New York Jets he failed to register a single touchdown in a 35-15 loss. And unfortunately he was just 34-43 as starter. 
4. Steve DeBerg
81.8 Passer Rating
DeBerg bounced around quite a bit early in his career. He, like Kenney, was also a late round pick in the 10th round in the 1977 NFL draft. With the 49ers bringing in Joe Montana, the Broncos bringing in John Elway, and the Buccaneers signing Steve Young, DeBerg didn’t land in Kansas City until 1988. Despite only playing 52 games for the Chiefs, an aged DeBerg managed to win 31 times, including a playoff game over rival Oakland Raiders.
DeBerg’s 1990 season (23TDs 4INTs) was great, but he was only a Chiefs quarterback for four seasons and showed inaccuracy at times. 
3. Joe Montana
85.0 Passer Rating
Montana made his legacy in San Fransisco, but he wouldn’t go without a fight. He won two playoff games for the Chiefs and nearly took them to the Super Bowl in 1994. Montana is the last Chiefs quarterback to win a playoff game. He brought his fourth quarter clutch abilities from the 49ers with him. In his final season, the Chiefs defeated the 49ers in a much anticipated “revenge game” of Montana vs. Young. Chiefs won 24-17.
Montana had a great stint with the Chiefs, but he only started 25 games and inherited a good team as well. 
2. Trent Green
87.3 Passer Rating
Another high drafted quarterback who finds destiny in Kansas City. Green was drafted in the eighth round.
So many memorable battles and shootouts with Peyton Manning and other quarterbacks with one punt and sometimes none at all. It’s really unfortunate he never had a quality defense to back him up. Green never won a playoff game, but who could blame him when both playoff match-ups were against Manning. Green still holds Chiefs franchise records for most passing yards in a single season, completion percentage in a season, career completion percentage, and career passer rating. 
1. Len Dawson
83.2 Passer Rating
As if there was any doubt. Dawson is a Hall of Fame quarterback who guided the Kansas City Chiefs to two Super Bowls, including a monumental upset victory in Super Bowl four. For his performance in the big game, Dawson was awarded Super Bowl MVP. Despite being small and short, Dawson was an underrated mobile quarterback who was known for playing through pain. He would also win the 1962 AFL Championship as a member of the Dallas Texans.
Despite playing in a league with only 14 games, Dawson still holds the Chiefs record for most and second most touchdowns thrown in a single season with 29 and 30. 
Keep in mind, these stats shown are only what the quarterback has acquired in a Chiefs uniform. You can view them here as well.